libmongocrypt-helper 1.7.4.0.1001 → 1.8.0.0.1001

data/ext/libmongocrypt/libmongocrypt/src/mongocrypt-marking.c

@@ -16,197 +16,184 @@
 
 #include "mc-fle-blob-subtype-private.h"
 #include "mc-fle2-encryption-placeholder-private.h"
+#include "mc-fle2-find-equality-payload-private-v2.h"
 #include "mc-fle2-find-equality-payload-private.h"
+#include "mc-fle2-find-range-payload-private-v2.h"
 #include "mc-fle2-find-range-payload-private.h"
+#include "mc-fle2-insert-update-payload-private-v2.h"
 #include "mc-fle2-insert-update-payload-private.h"
 #include "mc-fle2-payload-uev-private.h"
-#include "mc-range-mincover-private.h"
-#include "mc-range-encoding-private.h"
+#include "mc-fle2-payload-uev-v2-private.h"
 #include "mc-range-edge-generation-private.h"
+#include "mc-range-encoding-private.h"
+#include "mc-range-mincover-private.h"
 #include "mc-tokens-private.h"
-#include "mongocrypt.h"
 #include "mongocrypt-buffer-private.h"
 #include "mongocrypt-ciphertext-private.h"
 #include "mongocrypt-crypto-private.h"
 #include "mongocrypt-key-broker-private.h"
 #include "mongocrypt-marking-private.h"
 #include "mongocrypt-util-private.h" // mc_bson_type_to_string
+#include "mongocrypt.h"
 
 #include <math.h> // isinf
 
 static bool
-_mongocrypt_marking_parse_fle1_placeholder (const bson_t *in,
-                                            _mongocrypt_marking_t *out,
-                                            mongocrypt_status_t *status)
-{
-   bson_iter_t iter;
-   bool has_ki = false, has_ka = false, has_a = false, has_v = false;
-
-   BSON_ASSERT_PARAM (in);
-   BSON_ASSERT_PARAM (out);
-
-   out->type = MONGOCRYPT_MARKING_FLE1_BY_ID;
-
-   if (!bson_iter_init (&iter, in)) {
-      CLIENT_ERR ("invalid BSON");
-      return false;
-   }
-
-   while (bson_iter_next (&iter)) {
-      const char *field;
-
-      field = bson_iter_key (&iter);
-      BSON_ASSERT (field);
-      if (0 == strcmp ("ki", field)) {
-         has_ki = true;
-         if (!_mongocrypt_buffer_from_uuid_iter (&out->key_id, &iter)) {
-            CLIENT_ERR ("key id must be a UUID");
-            return false;
-         }
-         continue;
-      }
-
-      if (0 == strcmp ("ka", field)) {
-         has_ka = true;
-         /* Some bson_value types are not allowed to be key alt names */
-         const bson_value_t *value;
-
-         value = bson_iter_value (&iter);
-
-         if (!BSON_ITER_HOLDS_UTF8 (&iter)) {
-            CLIENT_ERR ("key alt name must be a UTF8");
-            return false;
-         }
-         /* CDRIVER-3100 We must make a copy of this value; the result of
-          * bson_iter_value is ephemeral. */
-         bson_value_copy (value, &out->key_alt_name);
-         out->type = MONGOCRYPT_MARKING_FLE1_BY_ALTNAME;
-         continue;
-      }
-
-      if (0 == strcmp ("v", field)) {
-         has_v = true;
-         memcpy (&out->v_iter, &iter, sizeof (bson_iter_t));
-         continue;
-      }
-
-
-      if (0 == strcmp ("a", field)) {
-         int32_t algorithm;
-
-         has_a = true;
-         if (!BSON_ITER_HOLDS_INT32 (&iter)) {
-            CLIENT_ERR ("invalid marking, 'a' must be an int32");
-            return false;
-         }
-         algorithm = bson_iter_int32 (&iter);
-         if (algorithm != MONGOCRYPT_ENCRYPTION_ALGORITHM_DETERMINISTIC &&
-             algorithm != MONGOCRYPT_ENCRYPTION_ALGORITHM_RANDOM) {
-            CLIENT_ERR ("invalid algorithm value: %d", algorithm);
-            return false;
-         }
-         out->algorithm = (mongocrypt_encryption_algorithm_t) algorithm;
-         continue;
-      }
-
-      CLIENT_ERR ("unrecognized field '%s'", field);
-      return false;
-   }
-
-   if (!has_v) {
-      CLIENT_ERR ("no 'v' specified");
-      return false;
-   }
-
-   if (!has_ki && !has_ka) {
-      CLIENT_ERR ("neither 'ki' nor 'ka' specified");
-      return false;
-   }
-
-   if (has_ki && has_ka) {
-      CLIENT_ERR ("both 'ki' and 'ka' specified");
-      return false;
-   }
-
-   if (!has_a) {
-      CLIENT_ERR ("no 'a' specified");
-      return false;
-   }
-
-   return true;
-}
+_mongocrypt_marking_parse_fle1_placeholder(const bson_t *in, _mongocrypt_marking_t *out, mongocrypt_status_t *status) {
+    bson_iter_t iter;
+    bool has_ki = false, has_ka = false, has_a = false, has_v = false;
+
+    BSON_ASSERT_PARAM(in);
+    BSON_ASSERT_PARAM(out);
+
+    out->type = MONGOCRYPT_MARKING_FLE1_BY_ID;
+
+    if (!bson_iter_init(&iter, in)) {
+        CLIENT_ERR("invalid BSON");
+        return false;
+    }
+
+    while (bson_iter_next(&iter)) {
+        const char *field;
+
+        field = bson_iter_key(&iter);
+        BSON_ASSERT(field);
+        if (0 == strcmp("ki", field)) {
+            has_ki = true;
+            if (!_mongocrypt_buffer_from_uuid_iter(&out->key_id, &iter)) {
+                CLIENT_ERR("key id must be a UUID");
+                return false;
+            }
+            continue;
+        }
 
-static bool
-_mongocrypt_marking_parse_fle2_placeholder (const bson_t *in,
-                                            _mongocrypt_marking_t *out,
-                                            mongocrypt_status_t *status)
-{
-   BSON_ASSERT_PARAM (in);
-   BSON_ASSERT_PARAM (out);
-
-   out->type = MONGOCRYPT_MARKING_FLE2_ENCRYPTION;
-   return mc_FLE2EncryptionPlaceholder_parse (&out->fle2, in, status);
-}
+        if (0 == strcmp("ka", field)) {
+            has_ka = true;
+            /* Some bson_value types are not allowed to be key alt names */
+            const bson_value_t *value;
 
-bool
-_mongocrypt_marking_parse_unowned (const _mongocrypt_buffer_t *in,
-                                   _mongocrypt_marking_t *out,
-                                   mongocrypt_status_t *status)
-{
-   bson_t bson;
-
-   BSON_ASSERT_PARAM (in);
-   BSON_ASSERT_PARAM (out);
-
-   _mongocrypt_marking_init (out);
-   /* 5 for minimal BSON object, plus one for blob subtype */
-   if (in->len < 6) {
-      CLIENT_ERR ("invalid marking, length < 6");
-      return false;
-   }
-
-   if (!bson_init_static (&bson, in->data + 1, in->len - 1) ||
-       !bson_validate (&bson, BSON_VALIDATE_NONE, NULL)) {
-      CLIENT_ERR ("invalid BSON");
-      return false;
-   }
-
-   if (in->data[0] == MC_SUBTYPE_FLE1EncryptionPlaceholder) {
-      return _mongocrypt_marking_parse_fle1_placeholder (&bson, out, status);
-   } else if (in->data[0] == MC_SUBTYPE_FLE2EncryptionPlaceholder) {
-      return _mongocrypt_marking_parse_fle2_placeholder (&bson, out, status);
-   } else {
-      CLIENT_ERR ("invalid marking, first byte must be 0 or 3");
-      return false;
-   }
+            value = bson_iter_value(&iter);
+
+            if (!BSON_ITER_HOLDS_UTF8(&iter)) {
+                CLIENT_ERR("key alt name must be a UTF8");
+                return false;
+            }
+            /* CDRIVER-3100 We must make a copy of this value; the result of
+             * bson_iter_value is ephemeral. */
+            bson_value_copy(value, &out->key_alt_name);
+            out->type = MONGOCRYPT_MARKING_FLE1_BY_ALTNAME;
+            continue;
+        }
+
+        if (0 == strcmp("v", field)) {
+            has_v = true;
+            memcpy(&out->v_iter, &iter, sizeof(bson_iter_t));
+            continue;
+        }
+
+        if (0 == strcmp("a", field)) {
+            int32_t algorithm;
+
+            has_a = true;
+            if (!BSON_ITER_HOLDS_INT32(&iter)) {
+                CLIENT_ERR("invalid marking, 'a' must be an int32");
+                return false;
+            }
+            algorithm = bson_iter_int32(&iter);
+            if (algorithm != MONGOCRYPT_ENCRYPTION_ALGORITHM_DETERMINISTIC
+                && algorithm != MONGOCRYPT_ENCRYPTION_ALGORITHM_RANDOM) {
+                CLIENT_ERR("invalid algorithm value: %d", algorithm);
+                return false;
+            }
+            out->algorithm = (mongocrypt_encryption_algorithm_t)algorithm;
+            continue;
+        }
+
+        CLIENT_ERR("unrecognized field '%s'", field);
+        return false;
+    }
+
+    if (!has_v) {
+        CLIENT_ERR("no 'v' specified");
+        return false;
+    }
+
+    if (!has_ki && !has_ka) {
+        CLIENT_ERR("neither 'ki' nor 'ka' specified");
+        return false;
+    }
+
+    if (has_ki && has_ka) {
+        CLIENT_ERR("both 'ki' and 'ka' specified");
+        return false;
+    }
+
+    if (!has_a) {
+        CLIENT_ERR("no 'a' specified");
+        return false;
+    }
+
+    return true;
 }
 
+static bool
+_mongocrypt_marking_parse_fle2_placeholder(const bson_t *in, _mongocrypt_marking_t *out, mongocrypt_status_t *status) {
+    BSON_ASSERT_PARAM(in);
+    BSON_ASSERT_PARAM(out);
 
-void
-_mongocrypt_marking_init (_mongocrypt_marking_t *marking)
-{
-   BSON_ASSERT_PARAM (marking);
+    out->type = MONGOCRYPT_MARKING_FLE2_ENCRYPTION;
+    return mc_FLE2EncryptionPlaceholder_parse(&out->fle2, in, status);
+}
 
-   memset (marking, 0, sizeof (*marking));
+bool _mongocrypt_marking_parse_unowned(const _mongocrypt_buffer_t *in,
+                                       _mongocrypt_marking_t *out,
+                                       mongocrypt_status_t *status) {
+    bson_t bson;
+
+    BSON_ASSERT_PARAM(in);
+    BSON_ASSERT_PARAM(out);
+
+    _mongocrypt_marking_init(out);
+    /* 5 for minimal BSON object, plus one for blob subtype */
+    if (in->len < 6) {
+        CLIENT_ERR("invalid marking, length < 6");
+        return false;
+    }
+
+    if (!bson_init_static(&bson, in->data + 1, in->len - 1) || !bson_validate(&bson, BSON_VALIDATE_NONE, NULL)) {
+        CLIENT_ERR("invalid BSON");
+        return false;
+    }
+
+    if (in->data[0] == MC_SUBTYPE_FLE1EncryptionPlaceholder) {
+        return _mongocrypt_marking_parse_fle1_placeholder(&bson, out, status);
+    } else if (in->data[0] == MC_SUBTYPE_FLE2EncryptionPlaceholder) {
+        return _mongocrypt_marking_parse_fle2_placeholder(&bson, out, status);
+    } else {
+        CLIENT_ERR("invalid marking, first byte must be 0 or 3");
+        return false;
+    }
 }
 
+void _mongocrypt_marking_init(_mongocrypt_marking_t *marking) {
+    BSON_ASSERT_PARAM(marking);
 
-void
-_mongocrypt_marking_cleanup (_mongocrypt_marking_t *marking)
-{
-   if (!marking) {
-      return;
-   }
-   if (marking->type == MONGOCRYPT_MARKING_FLE2_ENCRYPTION) {
-      mc_FLE2EncryptionPlaceholder_cleanup (&marking->fle2);
-      return;
-   }
-
-   // else FLE1
-   _mongocrypt_buffer_cleanup (&marking->key_id);
-   bson_value_destroy (&marking->key_alt_name);
+    memset(marking, 0, sizeof(*marking));
 }
 
+void _mongocrypt_marking_cleanup(_mongocrypt_marking_t *marking) {
+    if (!marking) {
+        return;
+    }
+    if (marking->type == MONGOCRYPT_MARKING_FLE2_ENCRYPTION) {
+        mc_FLE2EncryptionPlaceholder_cleanup(&marking->fle2);
+        return;
+    }
+
+    // else FLE1
+    _mongocrypt_buffer_cleanup(&marking->key_id);
+    bson_value_destroy(&marking->key_alt_name);
+}
 
 /**
  * Calculates:
@@ -221,1404 +208,1768 @@ _mongocrypt_marking_cleanup (_mongocrypt_marking_t *marking)
  * E?CDerivedFromDataTokenAndCounter is saved to out,
  * which is initialized even on failure.
  */
-#define DERIVE_TOKEN_IMPL(Name)                                                \
-   static bool _fle2_derive_##Name##_token (                                   \
-      _mongocrypt_crypto_t *crypto,                                            \
-      _mongocrypt_buffer_t *out,                                               \
-      const mc_CollectionsLevel1Token_t *level1Token,                          \
-      const _mongocrypt_buffer_t *value,                                       \
-      bool useCounter,                                                         \
-      int64_t counter,                                                         \
-      mongocrypt_status_t *status)                                             \
-   {                                                                           \
-      BSON_ASSERT_PARAM (crypto);                                              \
-      BSON_ASSERT_PARAM (out);                                                 \
-      BSON_ASSERT_PARAM (level1Token);                                         \
-      BSON_ASSERT_PARAM (value);                                               \
-                                                                               \
-      _mongocrypt_buffer_init (out);                                           \
-                                                                               \
-      mc_##Name##Token_t *token =                                              \
-         mc_##Name##Token_new (crypto, level1Token, status);                   \
-      if (!token) {                                                            \
-         return false;                                                         \
-      }                                                                        \
-                                                                               \
-      mc_##Name##DerivedFromDataToken_t *fromDataToken =                       \
-         mc_##Name##DerivedFromDataToken_new (crypto, token, value, status);   \
-      mc_##Name##Token_destroy (token);                                        \
-      if (!fromDataToken) {                                                    \
-         return false;                                                         \
-      }                                                                        \
-                                                                               \
-      if (!useCounter) {                                                       \
-         /* FindEqualityPayload uses *fromDataToken */                         \
-         _mongocrypt_buffer_copy_to (                                          \
-            mc_##Name##DerivedFromDataToken_get (fromDataToken), out);         \
-         mc_##Name##DerivedFromDataToken_destroy (fromDataToken);              \
-         return true;                                                          \
-      }                                                                        \
-                                                                               \
-      BSON_ASSERT (counter >= 0);                                              \
-      /* InsertUpdatePayload continues through *fromDataTokenAndCounter */     \
-      mc_##Name##DerivedFromDataTokenAndCounter_t *fromTokenAndCounter =       \
-         mc_##Name##DerivedFromDataTokenAndCounter_new (                       \
-            crypto, fromDataToken, (uint64_t) counter, status);                \
-      mc_##Name##DerivedFromDataToken_destroy (fromDataToken);                 \
-      if (!fromTokenAndCounter) {                                              \
-         return false;                                                         \
-      }                                                                        \
-                                                                               \
-      _mongocrypt_buffer_copy_to (                                             \
-         mc_##Name##DerivedFromDataTokenAndCounter_get (fromTokenAndCounter),  \
-         out);                                                                 \
-      mc_##Name##DerivedFromDataTokenAndCounter_destroy (fromTokenAndCounter); \
-                                                                               \
-      return true;                                                             \
-   }
-
-DERIVE_TOKEN_IMPL (EDC)
-DERIVE_TOKEN_IMPL (ESC)
-DERIVE_TOKEN_IMPL (ECC)
+#define DERIVE_TOKEN_IMPL(Name)                                                                                        \
+    static bool _fle2_derive_##Name##_token(_mongocrypt_crypto_t *crypto,                                              \
+                                            _mongocrypt_buffer_t *out,                                                 \
+                                            const mc_CollectionsLevel1Token_t *level1Token,                            \
+                                            const _mongocrypt_buffer_t *value,                                         \
+                                            bool useCounter,                                                           \
+                                            int64_t counter,                                                           \
+                                            mongocrypt_status_t *status) {                                             \
+        BSON_ASSERT_PARAM(crypto);                                                                                     \
+        BSON_ASSERT_PARAM(out);                                                                                        \
+        BSON_ASSERT_PARAM(level1Token);                                                                                \
+        BSON_ASSERT_PARAM(value);                                                                                      \
+                                                                                                                       \
+        _mongocrypt_buffer_init(out);                                                                                  \
+                                                                                                                       \
+        mc_##Name##Token_t *token = mc_##Name##Token_new(crypto, level1Token, status);                                 \
+        if (!token) {                                                                                                  \
+            return false;                                                                                              \
+        }                                                                                                              \
+                                                                                                                       \
+        mc_##Name##DerivedFromDataToken_t *fromDataToken =                                                             \
+            mc_##Name##DerivedFromDataToken_new(crypto, token, value, status);                                         \
+        mc_##Name##Token_destroy(token);                                                                               \
+        if (!fromDataToken) {                                                                                          \
+            return false;                                                                                              \
+        }                                                                                                              \
+                                                                                                                       \
+        if (!useCounter) {                                                                                             \
+            /* FindEqualityPayload uses *fromDataToken */                                                              \
+            _mongocrypt_buffer_copy_to(mc_##Name##DerivedFromDataToken_get(fromDataToken), out);                       \
+            mc_##Name##DerivedFromDataToken_destroy(fromDataToken);                                                    \
+            return true;                                                                                               \
+        }                                                                                                              \
+                                                                                                                       \
+        BSON_ASSERT(counter >= 0);                                                                                     \
+        /* InsertUpdatePayload continues through *fromDataTokenAndCounter */                                           \
+        mc_##Name##DerivedFromDataTokenAndCounter_t *fromTokenAndCounter =                                             \
+            mc_##Name##DerivedFromDataTokenAndCounter_new(crypto, fromDataToken, (uint64_t)counter, status);           \
+        mc_##Name##DerivedFromDataToken_destroy(fromDataToken);                                                        \
+        if (!fromTokenAndCounter) {                                                                                    \
+            return false;                                                                                              \
+        }                                                                                                              \
+                                                                                                                       \
+        _mongocrypt_buffer_copy_to(mc_##Name##DerivedFromDataTokenAndCounter_get(fromTokenAndCounter), out);           \
+        mc_##Name##DerivedFromDataTokenAndCounter_destroy(fromTokenAndCounter);                                        \
+                                                                                                                       \
+        return true;                                                                                                   \
+    }
+
+DERIVE_TOKEN_IMPL(EDC)
+DERIVE_TOKEN_IMPL(ESC)
+DERIVE_TOKEN_IMPL(ECC)
 
 #undef DERIVE_TOKEN_IMPL
 
-static bool
-_fle2_placeholder_aes_ctr_encrypt (_mongocrypt_key_broker_t *kb,
-                                   const _mongocrypt_buffer_t *key,
-                                   const _mongocrypt_buffer_t *in,
-                                   _mongocrypt_buffer_t *out,
-                                   mongocrypt_status_t *status)
-{
-   BSON_ASSERT_PARAM (kb);
-   BSON_ASSERT_PARAM (key);
-   BSON_ASSERT_PARAM (in);
-   BSON_ASSERT_PARAM (out);
-   BSON_ASSERT (kb->crypt);
-
-   _mongocrypt_crypto_t *crypto = kb->crypt->crypto;
-   _mongocrypt_buffer_t iv;
-   const uint32_t cipherlen =
-      _mongocrypt_fle2_calculate_ciphertext_len (in->len, status);
-   if (cipherlen == 0) {
-      return false;
-   }
-   uint32_t written = 0;
-
-   _mongocrypt_buffer_init_size (out, cipherlen);
-
-   BSON_ASSERT (
-      _mongocrypt_buffer_from_subrange (&iv, out, 0, MONGOCRYPT_IV_LEN));
-   if (!_mongocrypt_random (crypto, &iv, MONGOCRYPT_IV_LEN, status)) {
-      return false;
-   }
-
-   if (!_mongocrypt_fle2_do_encryption (
-          crypto, &iv, key, in, out, &written, status)) {
-      _mongocrypt_buffer_cleanup (out);
-      _mongocrypt_buffer_init (out);
-      return false;
-   }
-
-   return true;
+static bool _fle2_derive_serverDerivedFromDataToken(_mongocrypt_crypto_t *crypto,
+                                                    _mongocrypt_buffer_t *out,
+                                                    const mc_ServerTokenDerivationLevel1Token_t *level1Token,
+                                                    const _mongocrypt_buffer_t *value,
+                                                    mongocrypt_status_t *status) {
+    BSON_ASSERT_PARAM(crypto);
+    BSON_ASSERT_PARAM(out);
+    BSON_ASSERT_PARAM(level1Token);
+    BSON_ASSERT_PARAM(value);
+    BSON_ASSERT_PARAM(status);
+
+    _mongocrypt_buffer_init(out);
+
+    mc_ServerDerivedFromDataToken_t *token = mc_ServerDerivedFromDataToken_new(crypto, level1Token, value, status);
+    if (!token) {
+        return false;
+    }
+
+    _mongocrypt_buffer_copy_to(mc_ServerDerivedFromDataToken_get(token), out);
+    mc_ServerDerivedFromDataToken_destroy(token);
+    return true;
 }
 
+static bool _fle2_placeholder_aes_ctr_encrypt(_mongocrypt_crypto_t *crypto,
+                                              const _mongocrypt_buffer_t *key,
+                                              const _mongocrypt_buffer_t *in,
+                                              _mongocrypt_buffer_t *out,
+                                              mongocrypt_status_t *status) {
+    const _mongocrypt_value_encryption_algorithm_t *fle2alg = _mcFLE2Algorithm();
+    BSON_ASSERT_PARAM(crypto);
+    BSON_ASSERT_PARAM(key);
+    BSON_ASSERT_PARAM(in);
+    BSON_ASSERT_PARAM(out);
+
+    _mongocrypt_buffer_t iv;
+    const uint32_t cipherlen = fle2alg->get_ciphertext_len(in->len, status);
+    if (cipherlen == 0) {
+        return false;
+    }
+    uint32_t written = 0;
+
+    _mongocrypt_buffer_init_size(out, cipherlen);
+
+    BSON_ASSERT(_mongocrypt_buffer_from_subrange(&iv, out, 0, MONGOCRYPT_IV_LEN));
+    if (!_mongocrypt_random(crypto, &iv, MONGOCRYPT_IV_LEN, status)) {
+        return false;
+    }
+
+    if (!fle2alg->do_encrypt(crypto, &iv, NULL /* aad */, key, in, out, &written, status)) {
+        _mongocrypt_buffer_cleanup(out);
+        _mongocrypt_buffer_init(out);
+        return false;
+    }
+
+    return true;
+}
 
-static bool
-_fle2_placeholder_aead_encrypt (_mongocrypt_key_broker_t *kb,
-                                const _mongocrypt_buffer_t *keyId,
-                                const _mongocrypt_buffer_t *in,
-                                _mongocrypt_buffer_t *out,
-                                mongocrypt_status_t *status)
-{
-   BSON_ASSERT_PARAM (kb);
-   BSON_ASSERT_PARAM (keyId);
-   BSON_ASSERT_PARAM (in);
-   BSON_ASSERT_PARAM (out);
-   BSON_ASSERT (kb->crypt);
-
-   _mongocrypt_crypto_t *crypto = kb->crypt->crypto;
-   _mongocrypt_buffer_t iv, key;
-   const uint32_t cipherlen =
-      _mongocrypt_fle2aead_calculate_ciphertext_len (in->len, status);
-   if (cipherlen == 0) {
-      return false;
-   }
-   uint32_t written = 0;
-   bool res;
-
-   if (!_mongocrypt_key_broker_decrypted_key_by_id (kb, keyId, &key)) {
-      CLIENT_ERR ("unable to retrieve key");
-      return false;
-   }
-
-   _mongocrypt_buffer_init_size (&iv, MONGOCRYPT_IV_LEN);
-   if (!_mongocrypt_random (crypto, &iv, iv.len, status)) {
-      _mongocrypt_buffer_cleanup (&key);
-      return false;
-   }
-
-   _mongocrypt_buffer_init_size (out, cipherlen);
-   res = _mongocrypt_fle2aead_do_encryption (
-      crypto, &iv, keyId, &key, in, out, &written, status);
-   _mongocrypt_buffer_cleanup (&key);
-   _mongocrypt_buffer_cleanup (&iv);
-
-   if (!res) {
-      _mongocrypt_buffer_cleanup (out);
-      _mongocrypt_buffer_init (out);
-      return false;
-   }
-
-   return true;
+static bool _fle2_placeholder_aes_aead_encrypt(_mongocrypt_key_broker_t *kb,
+                                               const _mongocrypt_value_encryption_algorithm_t *algorithm,
+                                               _mongocrypt_buffer_t *out,
+                                               const _mongocrypt_buffer_t *keyId,
+                                               const _mongocrypt_buffer_t *in,
+                                               mongocrypt_status_t *status) {
+    BSON_ASSERT_PARAM(kb);
+    BSON_ASSERT_PARAM(keyId);
+    BSON_ASSERT_PARAM(in);
+    BSON_ASSERT_PARAM(out);
+    BSON_ASSERT(kb->crypt);
+
+    _mongocrypt_crypto_t *crypto = kb->crypt->crypto;
+    _mongocrypt_buffer_t iv, key;
+    const uint32_t cipherlen = algorithm->get_ciphertext_len(in->len, status);
+    if (cipherlen == 0) {
+        return false;
+    }
+    uint32_t written = 0;
+    bool res;
+
+    if (!_mongocrypt_key_broker_decrypted_key_by_id(kb, keyId, &key)) {
+        CLIENT_ERR("unable to retrieve key");
+        return false;
+    }
+
+    _mongocrypt_buffer_init_size(&iv, MONGOCRYPT_IV_LEN);
+    if (!_mongocrypt_random(crypto, &iv, iv.len, status)) {
+        _mongocrypt_buffer_cleanup(&key);
+        return false;
+    }
+
+    _mongocrypt_buffer_init_size(out, cipherlen);
+    res = algorithm->do_encrypt(crypto, &iv, keyId, &key, in, out, &written, status);
+    _mongocrypt_buffer_cleanup(&key);
+    _mongocrypt_buffer_cleanup(&iv);
+
+    if (!res) {
+        _mongocrypt_buffer_cleanup(out);
+        _mongocrypt_buffer_init(out);
+        return false;
+    }
+
+    return true;
 }
 
+// p := EncryptCTR(ECOCToken, ESCDerivedFromDataTokenAndCounter ||
+//                            ECCDerivedFromDataTokenAndCounter)
+static bool _fle2_derive_encrypted_token(_mongocrypt_crypto_t *crypto,
+                                         _mongocrypt_buffer_t *out,
+                                         const mc_CollectionsLevel1Token_t *collectionsLevel1Token,
+                                         const _mongocrypt_buffer_t *escDerivedToken,
+                                         const _mongocrypt_buffer_t *eccDerivedToken,
+                                         mongocrypt_status_t *status) {
+    mc_ECOCToken_t *ecocToken = mc_ECOCToken_new(crypto, collectionsLevel1Token, status);
+    if (!ecocToken) {
+        return false;
+    }
+
+    _mongocrypt_buffer_t tmp;
+    _mongocrypt_buffer_init(&tmp);
+    const _mongocrypt_buffer_t *p = &tmp;
+    if (!eccDerivedToken) {
+        // FLE2v2
+        p = escDerivedToken;
+    } else {
+        // FLE2v1
+        const _mongocrypt_buffer_t tokens[] = {*escDerivedToken, *eccDerivedToken};
+        _mongocrypt_buffer_concat(&tmp, tokens, 2);
+    }
+
+    const bool ok = _fle2_placeholder_aes_ctr_encrypt(crypto, mc_ECOCToken_get(ecocToken), p, out, status);
+    _mongocrypt_buffer_cleanup(&tmp);
+    mc_ECOCToken_destroy(ecocToken);
+    return ok;
+}
 
 // Field derivations shared by both INSERT and FIND payloads.
 typedef struct {
-   _mongocrypt_buffer_t tokenKey;
-   mc_CollectionsLevel1Token_t *collectionsLevel1Token;
-   _mongocrypt_buffer_t edcDerivedToken;
-   _mongocrypt_buffer_t escDerivedToken;
-   _mongocrypt_buffer_t eccDerivedToken;
+    _mongocrypt_buffer_t tokenKey;
+    mc_CollectionsLevel1Token_t *collectionsLevel1Token;
+    mc_ServerDataEncryptionLevel1Token_t *serverDataEncryptionLevel1Token;
+    mc_ServerTokenDerivationLevel1Token_t *serverTokenDerivationLevel1Token; // v2
+    _mongocrypt_buffer_t edcDerivedToken;
+    _mongocrypt_buffer_t escDerivedToken;
+    _mongocrypt_buffer_t eccDerivedToken;            // v1
+    _mongocrypt_buffer_t serverDerivedFromDataToken; // v2
 } _FLE2EncryptedPayloadCommon_t;
 
-static void
-_FLE2EncryptedPayloadCommon_cleanup (_FLE2EncryptedPayloadCommon_t *common)
-{
-   if (!common) {
-      return;
-   }
-
-   _mongocrypt_buffer_cleanup (&common->tokenKey);
-   mc_CollectionsLevel1Token_destroy (common->collectionsLevel1Token);
-   _mongocrypt_buffer_cleanup (&common->edcDerivedToken);
-   _mongocrypt_buffer_cleanup (&common->escDerivedToken);
-   _mongocrypt_buffer_cleanup (&common->eccDerivedToken);
-   memset (common, 0, sizeof (*common));
+static void _FLE2EncryptedPayloadCommon_cleanup(_FLE2EncryptedPayloadCommon_t *common) {
+    if (!common) {
+        return;
+    }
+
+    _mongocrypt_buffer_cleanup(&common->tokenKey);
+    mc_CollectionsLevel1Token_destroy(common->collectionsLevel1Token);
+    mc_ServerDataEncryptionLevel1Token_destroy(common->serverDataEncryptionLevel1Token);
+    mc_ServerTokenDerivationLevel1Token_destroy(common->serverTokenDerivationLevel1Token);
+    _mongocrypt_buffer_cleanup(&common->edcDerivedToken);
+    _mongocrypt_buffer_cleanup(&common->escDerivedToken);
+    _mongocrypt_buffer_cleanup(&common->eccDerivedToken);
+    _mongocrypt_buffer_cleanup(&common->serverDerivedFromDataToken);
+    memset(common, 0, sizeof(*common));
 }
 
 // _get_tokenKey returns the tokenKey identified by indexKeyId.
 // Returns false on error.
-static bool
-_get_tokenKey (_mongocrypt_key_broker_t *kb,
-               const _mongocrypt_buffer_t *indexKeyId,
-               _mongocrypt_buffer_t *tokenKey,
-               mongocrypt_status_t *status)
-{
-   BSON_ASSERT_PARAM (kb);
-   BSON_ASSERT_PARAM (indexKeyId);
-   BSON_ASSERT_PARAM (tokenKey);
-
-   _mongocrypt_buffer_t indexKey = {0};
-   _mongocrypt_buffer_init (tokenKey);
-
-   if (!_mongocrypt_key_broker_decrypted_key_by_id (
-          kb, indexKeyId, &indexKey)) {
-      CLIENT_ERR ("unable to retrieve key");
-      return false;
-   }
-
-   if (indexKey.len != MONGOCRYPT_KEY_LEN) {
-      CLIENT_ERR ("invalid indexKey, expected len=%" PRIu32
-                  ", got len=%" PRIu32,
-                  MONGOCRYPT_KEY_LEN,
-                  indexKey.len);
-      _mongocrypt_buffer_cleanup (&indexKey);
-      return false;
-   }
-
-   // indexKey is 3 equal sized keys: [Ke][Km][TokenKey]
-   BSON_ASSERT (MONGOCRYPT_KEY_LEN == (3 * MONGOCRYPT_TOKEN_KEY_LEN));
-   if (!_mongocrypt_buffer_copy_from_data_and_size (
-          tokenKey,
-          indexKey.data + (2 * MONGOCRYPT_TOKEN_KEY_LEN),
-          MONGOCRYPT_TOKEN_KEY_LEN)) {
-      CLIENT_ERR ("failed allocating memory for token key");
-      _mongocrypt_buffer_cleanup (&indexKey);
-      return false;
-   }
-   _mongocrypt_buffer_cleanup (&indexKey);
-   return true;
+static bool _get_tokenKey(_mongocrypt_key_broker_t *kb,
+                          const _mongocrypt_buffer_t *indexKeyId,
+                          _mongocrypt_buffer_t *tokenKey,
+                          mongocrypt_status_t *status) {
+    BSON_ASSERT_PARAM(kb);
+    BSON_ASSERT_PARAM(indexKeyId);
+    BSON_ASSERT_PARAM(tokenKey);
+
+    _mongocrypt_buffer_t indexKey = {0};
+    _mongocrypt_buffer_init(tokenKey);
+
+    if (!_mongocrypt_key_broker_decrypted_key_by_id(kb, indexKeyId, &indexKey)) {
+        CLIENT_ERR("unable to retrieve key");
+        return false;
+    }
+
+    if (indexKey.len != MONGOCRYPT_KEY_LEN) {
+        CLIENT_ERR("invalid indexKey, expected len=%" PRIu32 ", got len=%" PRIu32, MONGOCRYPT_KEY_LEN, indexKey.len);
+        _mongocrypt_buffer_cleanup(&indexKey);
+        return false;
+    }
+
+    // indexKey is 3 equal sized keys: [Ke][Km][TokenKey]
+    BSON_ASSERT(MONGOCRYPT_KEY_LEN == (3 * MONGOCRYPT_TOKEN_KEY_LEN));
+    if (!_mongocrypt_buffer_copy_from_data_and_size(tokenKey,
+                                                    indexKey.data + (2 * MONGOCRYPT_TOKEN_KEY_LEN),
+                                                    MONGOCRYPT_TOKEN_KEY_LEN)) {
+        CLIENT_ERR("failed allocating memory for token key");
+        _mongocrypt_buffer_cleanup(&indexKey);
+        return false;
+    }
+    _mongocrypt_buffer_cleanup(&indexKey);
+    return true;
 }
 
-static bool
-_mongocrypt_fle2_placeholder_common (_mongocrypt_key_broker_t *kb,
-                                     _FLE2EncryptedPayloadCommon_t *ret,
-                                     const _mongocrypt_buffer_t *indexKeyId,
-                                     const _mongocrypt_buffer_t *value,
-                                     bool useCounter,
-                                     int64_t maxContentionCounter,
-                                     mongocrypt_status_t *status)
-{
-   BSON_ASSERT_PARAM (kb);
-   BSON_ASSERT_PARAM (ret);
-   BSON_ASSERT_PARAM (indexKeyId);
-   BSON_ASSERT_PARAM (value);
-
-   _mongocrypt_crypto_t *crypto = kb->crypt->crypto;
-   _mongocrypt_buffer_t indexKey = {0};
-   *ret = (_FLE2EncryptedPayloadCommon_t){{0}};
-
-   if (!_get_tokenKey (kb, indexKeyId, &ret->tokenKey, status)) {
-      goto fail;
-   }
-
-   ret->collectionsLevel1Token =
-      mc_CollectionsLevel1Token_new (crypto, &ret->tokenKey, status);
-   if (!ret->collectionsLevel1Token) {
-      CLIENT_ERR ("unable to derive collectionLevel1Token");
-      goto fail;
-   }
-
-   if (!_fle2_derive_EDC_token (crypto,
+static bool _mongocrypt_fle2_placeholder_common(_mongocrypt_key_broker_t *kb,
+                                                _FLE2EncryptedPayloadCommon_t *ret,
+                                                const _mongocrypt_buffer_t *indexKeyId,
+                                                const _mongocrypt_buffer_t *value,
+                                                bool useCounter,
+                                                int64_t maxContentionCounter,
+                                                mongocrypt_status_t *status) {
+    BSON_ASSERT_PARAM(kb);
+    BSON_ASSERT_PARAM(ret);
+    BSON_ASSERT_PARAM(indexKeyId);
+    BSON_ASSERT_PARAM(value);
+
+    _mongocrypt_crypto_t *crypto = kb->crypt->crypto;
+    _mongocrypt_buffer_t indexKey = {0};
+    *ret = (_FLE2EncryptedPayloadCommon_t){{0}};
+
+    if (!_get_tokenKey(kb, indexKeyId, &ret->tokenKey, status)) {
+        goto fail;
+    }
+
+    ret->collectionsLevel1Token = mc_CollectionsLevel1Token_new(crypto, &ret->tokenKey, status);
+    if (!ret->collectionsLevel1Token) {
+        CLIENT_ERR("unable to derive collectionLevel1Token");
+        goto fail;
+    }
+
+    ret->serverDataEncryptionLevel1Token = mc_ServerDataEncryptionLevel1Token_new(crypto, &ret->tokenKey, status);
+    if (!ret->serverDataEncryptionLevel1Token) {
+        CLIENT_ERR("unable to derive serverDataEncryptionLevel1Token");
+        goto fail;
+    }
+
+    if (!_fle2_derive_EDC_token(crypto,
                                 &ret->edcDerivedToken,
                                 ret->collectionsLevel1Token,
                                 value,
                                 useCounter,
                                 maxContentionCounter,
                                 status)) {
-      goto fail;
-   }
+        goto fail;
+    }
 
-   if (!_fle2_derive_ESC_token (crypto,
+    if (!_fle2_derive_ESC_token(crypto,
                                 &ret->escDerivedToken,
                                 ret->collectionsLevel1Token,
                                 value,
                                 useCounter,
                                 maxContentionCounter,
                                 status)) {
-      goto fail;
-   }
+        goto fail;
+    }
+
+    if (kb->crypt->opts.use_fle2_v2) {
+        /* FLE2v2 */
+        ret->serverTokenDerivationLevel1Token = mc_ServerTokenDerivationLevel1Token_new(crypto, &ret->tokenKey, status);
+        if (!ret->serverTokenDerivationLevel1Token) {
+            CLIENT_ERR("unable to derive serverTokenDerivationLevel1Token");
+            goto fail;
+        }
 
-   if (!_fle2_derive_ECC_token (crypto,
-                                &ret->eccDerivedToken,
-                                ret->collectionsLevel1Token,
-                                value,
-                                useCounter,
-                                maxContentionCounter,
-                                status)) {
-      goto fail;
-   }
+        if (!_fle2_derive_serverDerivedFromDataToken(crypto,
+                                                     &ret->serverDerivedFromDataToken,
+                                                     ret->serverTokenDerivationLevel1Token,
+                                                     value,
+                                                     status)) {
+            goto fail;
+        }
+    } else {
+        /* FLE2v1 */
+        if (!_fle2_derive_ECC_token(crypto,
+                                    &ret->eccDerivedToken,
+                                    ret->collectionsLevel1Token,
+                                    value,
+                                    useCounter,
+                                    maxContentionCounter,
+                                    status)) {
+            goto fail;
+        }
+    }
 
-   _mongocrypt_buffer_cleanup (&indexKey);
-   return true;
+    _mongocrypt_buffer_cleanup(&indexKey);
+    return true;
 
 fail:
-   _FLE2EncryptedPayloadCommon_cleanup (ret);
-   _mongocrypt_buffer_cleanup (&indexKey);
-   return false;
+    _FLE2EncryptedPayloadCommon_cleanup(ret);
+    _mongocrypt_buffer_cleanup(&indexKey);
+    return false;
 }
 
+// Shared implementation for insert/update and insert/update ForRange (v1)
+static bool _mongocrypt_fle2_placeholder_to_insert_update_common_v1(_mongocrypt_key_broker_t *kb,
+                                                                    mc_FLE2InsertUpdatePayload_t *out,
+                                                                    int64_t *contentionFactor,
+                                                                    _FLE2EncryptedPayloadCommon_t *common,
+                                                                    const mc_FLE2EncryptionPlaceholder_t *placeholder,
+                                                                    bson_iter_t *value_iter,
+                                                                    mongocrypt_status_t *status) {
+    BSON_ASSERT_PARAM(kb);
+    BSON_ASSERT_PARAM(out);
+    BSON_ASSERT_PARAM(common);
+    BSON_ASSERT_PARAM(placeholder);
+    BSON_ASSERT_PARAM(value_iter);
+    BSON_ASSERT(kb->crypt);
+    BSON_ASSERT(kb->crypt->opts.use_fle2_v2 == false);
+    BSON_ASSERT(placeholder->type == MONGOCRYPT_FLE2_PLACEHOLDER_TYPE_INSERT);
+
+    _mongocrypt_crypto_t *crypto = kb->crypt->crypto;
+    _mongocrypt_buffer_t value = {0};
+    bool res = false;
+
+    *contentionFactor = 0;
+    if (placeholder->maxContentionCounter > 0) {
+        /* Choose a random contentionFactor in the inclusive range [0,
+         * placeholder->maxContentionCounter] */
+        if (!_mongocrypt_random_int64(crypto, placeholder->maxContentionCounter + 1, contentionFactor, status)) {
+            goto fail;
+        }
+    }
+
+    _mongocrypt_buffer_from_iter(&value, value_iter);
+    if (!_mongocrypt_fle2_placeholder_common(kb,
+                                             common,
+                                             &placeholder->index_key_id,
+                                             &value,
+                                             true, /* derive tokens using counter */
+                                             *contentionFactor,
+                                             status)) {
+        goto fail;
+    }
+
+    // d := EDCDerivedToken
+    _mongocrypt_buffer_steal(&out->edcDerivedToken, &common->edcDerivedToken);
+    // s := ESCDerivedToken
+    _mongocrypt_buffer_steal(&out->escDerivedToken, &common->escDerivedToken);
+    // c := ECCDerivedToken
+    _mongocrypt_buffer_steal(&out->eccDerivedToken, &common->eccDerivedToken);
+
+    // p := EncryptCTR(ECOCToken, ESCDerivedFromDataTokenAndCounter ||
+    // ECCDerivedFromDataTokenAndCounter)
+    if (!_fle2_derive_encrypted_token(crypto,
+                                      &out->encryptedTokens,
+                                      common->collectionsLevel1Token,
+                                      &out->escDerivedToken,
+                                      &out->eccDerivedToken,
+                                      status)) {
+        goto fail;
+    }
+
+    _mongocrypt_buffer_copy_to(&placeholder->index_key_id,
+                               &out->indexKeyId); // u
+    out->valueType = bson_iter_type(value_iter);  // t
+
+    // v := UserKeyId + EncryptCTRAEAD(UserKey, value)
+    {
+        _mongocrypt_buffer_t ciphertext = {0};
+        if (!_fle2_placeholder_aes_aead_encrypt(kb,
+                                                _mcFLE2AEADAlgorithm(),
+                                                &ciphertext,
+                                                &placeholder->user_key_id,
+                                                &value,
+                                                status)) {
+            goto fail;
+        }
+        const _mongocrypt_buffer_t v[2] = {placeholder->user_key_id, ciphertext};
+        const bool ok = _mongocrypt_buffer_concat(&out->value, v, 2);
+        _mongocrypt_buffer_cleanup(&ciphertext);
+        if (!ok) {
+            goto fail;
+        }
+    }
 
-static bool
-_mongocrypt_fle2_placeholder_to_insert_update_ciphertext (
-   _mongocrypt_key_broker_t *kb,
-   _mongocrypt_marking_t *marking,
-   _mongocrypt_ciphertext_t *ciphertext,
-   mongocrypt_status_t *status)
-{
-   BSON_ASSERT_PARAM (kb);
-   BSON_ASSERT_PARAM (marking);
-   BSON_ASSERT_PARAM (ciphertext);
-   BSON_ASSERT (kb->crypt);
-
-   _mongocrypt_crypto_t *crypto = kb->crypt->crypto;
-   _FLE2EncryptedPayloadCommon_t common = {{0}};
-   _mongocrypt_buffer_t value = {0};
-   mc_FLE2EncryptionPlaceholder_t *placeholder = &marking->fle2;
-   mc_FLE2InsertUpdatePayload_t payload;
-   bool res = false;
-
-   BSON_ASSERT (marking->type == MONGOCRYPT_MARKING_FLE2_ENCRYPTION);
-   BSON_ASSERT (placeholder->type == MONGOCRYPT_FLE2_PLACEHOLDER_TYPE_INSERT);
-   _mongocrypt_ciphertext_init (ciphertext);
-   _mongocrypt_buffer_init (&value);
-   mc_FLE2InsertUpdatePayload_init (&payload);
-
-   _mongocrypt_buffer_from_iter (&value, &placeholder->v_iter);
-
-   int64_t contentionFactor = 0;
-   if (placeholder->maxContentionCounter > 0) {
-      /* Choose a random contentionFactor in the inclusive range [0,
-       * placeholder->maxContentionCounter] */
-      if (!_mongocrypt_random_int64 (crypto,
-                                     placeholder->maxContentionCounter + 1,
-                                     &contentionFactor,
-                                     status)) {
-         goto fail;
-      }
-   }
-
-   if (!_mongocrypt_fle2_placeholder_common (
-          kb,
-          &common,
-          &placeholder->index_key_id,
-          &value,
-          true, /* derive tokens using counter */
-          contentionFactor,
-          status)) {
-      goto fail;
-   }
-
-   // d := EDCDerivedToken
-   _mongocrypt_buffer_steal (&payload.edcDerivedToken, &common.edcDerivedToken);
-   // s := ESCDerivedToken
-   _mongocrypt_buffer_steal (&payload.escDerivedToken, &common.escDerivedToken);
-   // c := ECCDerivedToken
-   _mongocrypt_buffer_steal (&payload.eccDerivedToken, &common.eccDerivedToken);
-
-   // p := EncryptCTR(ECOCToken, ESCDerivedFromDataTokenAndCounter ||
-   // ECCDerivedFromDataTokenAndCounter)
-   {
-      _mongocrypt_buffer_t tokens[] = {payload.escDerivedToken,
-                                       payload.eccDerivedToken};
-      _mongocrypt_buffer_t p;
-      _mongocrypt_buffer_concat (&p, tokens, 2);
-      mc_ECOCToken_t *ecocToken =
-         mc_ECOCToken_new (crypto, common.collectionsLevel1Token, status);
-      if (!ecocToken) {
-         _mongocrypt_buffer_cleanup (&p);
-         goto fail;
-      }
-      bool ok = _fle2_placeholder_aes_ctr_encrypt (kb,
-                                                   mc_ECOCToken_get (ecocToken),
-                                                   &p,
-                                                   &payload.encryptedTokens,
-                                                   status);
-      _mongocrypt_buffer_cleanup (&p);
-      mc_ECOCToken_destroy (ecocToken);
-      if (!ok) {
-         goto fail;
-      }
-   }
-
-   _mongocrypt_buffer_copy_to (&placeholder->index_key_id,
-                               &payload.indexKeyId);          // u
-   payload.valueType = bson_iter_type (&placeholder->v_iter); // t
-
-   // v := UserKeyId + EncryptAEAD(UserKey, value)
-   {
-      _mongocrypt_buffer_t tmp[2] = {placeholder->user_key_id, {0}};
-      if (!_fle2_placeholder_aead_encrypt (
-             kb, &placeholder->user_key_id, &value, &tmp[1], status)) {
-         goto fail;
-      }
-      bool ok = _mongocrypt_buffer_concat (&payload.value, tmp, 2);
-      _mongocrypt_buffer_cleanup (&tmp[1]);
-      if (!ok) {
-         goto fail;
-      }
-   }
-
-   // e := ServerDataEncryptionLevel1Token
-   {
-      mc_ServerDataEncryptionLevel1Token_t *serverToken =
-         mc_ServerDataEncryptionLevel1Token_new (
-            crypto, &common.tokenKey, status);
-      if (!serverToken) {
-         goto fail;
-      }
-      _mongocrypt_buffer_copy_to (
-         mc_ServerDataEncryptionLevel1Token_get (serverToken),
-         &payload.serverEncryptionToken);
-      mc_ServerDataEncryptionLevel1Token_destroy (serverToken);
-   }
-
-   {
-      bson_t out;
-      bson_init (&out);
-      mc_FLE2InsertUpdatePayload_serialize (&payload, &out);
-      _mongocrypt_buffer_steal_from_bson (&ciphertext->data, &out);
-   }
-   // Do not set ciphertext->original_bson_type and ciphertext->key_id. They are
-   // not used for FLE2InsertUpdatePayload.
-   ciphertext->blob_subtype = MC_SUBTYPE_FLE2InsertUpdatePayload;
-
-   res = true;
+    // e := ServerDataEncryptionLevel1Token
+    _mongocrypt_buffer_copy_to(mc_ServerDataEncryptionLevel1Token_get(common->serverDataEncryptionLevel1Token),
+                               &out->serverEncryptionToken);
+
+    res = true;
 fail:
-   mc_FLE2InsertUpdatePayload_cleanup (&payload);
-   _mongocrypt_buffer_cleanup (&value);
-   _FLE2EncryptedPayloadCommon_cleanup (&common);
+    _mongocrypt_buffer_cleanup(&value);
+    return res;
+}
 
-   return res;
+/**
+ * Payload subtype 4: FLE2InsertUpdatePayload
+ *
+ * {d: EDC, s: ESC, c: ECC,
+ *  p: encToken, u: indexKeyId, t: type,
+ *  v: value, e: serverToken}
+ */
+static bool _mongocrypt_fle2_placeholder_to_insert_update_ciphertext_v1(_mongocrypt_key_broker_t *kb,
+                                                                        _mongocrypt_marking_t *marking,
+                                                                        _mongocrypt_ciphertext_t *ciphertext,
+                                                                        mongocrypt_status_t *status) {
+    BSON_ASSERT_PARAM(kb);
+    BSON_ASSERT_PARAM(marking);
+    BSON_ASSERT_PARAM(ciphertext);
+    BSON_ASSERT_PARAM(status);
+    BSON_ASSERT(kb->crypt);
+    BSON_ASSERT(kb->crypt->opts.use_fle2_v2 == false);
+    BSON_ASSERT(marking->type == MONGOCRYPT_MARKING_FLE2_ENCRYPTION);
+    BSON_ASSERT(marking->fle2.algorithm == MONGOCRYPT_FLE2_ALGORITHM_EQUALITY);
+
+    mc_FLE2EncryptionPlaceholder_t *placeholder = &marking->fle2;
+    _FLE2EncryptedPayloadCommon_t common = {{0}};
+    mc_FLE2InsertUpdatePayload_t payload;
+    mc_FLE2InsertUpdatePayload_init(&payload);
+    bool res = false;
+
+    int64_t contentionFactor = 0; /* ignored */
+    if (!_mongocrypt_fle2_placeholder_to_insert_update_common_v1(kb,
+                                                                 &payload,
+                                                                 &contentionFactor,
+                                                                 &common,
+                                                                 placeholder,
+                                                                 &placeholder->v_iter,
+                                                                 status)) {
+        goto fail;
+    }
+
+    {
+        bson_t out;
+        bson_init(&out);
+        mc_FLE2InsertUpdatePayload_serialize(&payload, &out);
+        _mongocrypt_buffer_steal_from_bson(&ciphertext->data, &out);
+    }
+    // Do not set ciphertext->original_bson_type and ciphertext->key_id. They are
+    // not used for FLE2InsertUpdatePayload.
+    ciphertext->blob_subtype = MC_SUBTYPE_FLE2InsertUpdatePayload;
+
+    res = true;
+fail:
+    mc_FLE2InsertUpdatePayload_cleanup(&payload);
+    _FLE2EncryptedPayloadCommon_cleanup(&common);
+
+    return res;
+}
+
+// Shared implementation for insert/update and insert/update ForRange (v2)
+static bool _mongocrypt_fle2_placeholder_to_insert_update_common(_mongocrypt_key_broker_t *kb,
+                                                                 mc_FLE2InsertUpdatePayloadV2_t *out,
+                                                                 _FLE2EncryptedPayloadCommon_t *common,
+                                                                 const mc_FLE2EncryptionPlaceholder_t *placeholder,
+                                                                 bson_iter_t *value_iter,
+                                                                 mongocrypt_status_t *status) {
+    BSON_ASSERT_PARAM(kb);
+    BSON_ASSERT_PARAM(out);
+    BSON_ASSERT_PARAM(common);
+    BSON_ASSERT_PARAM(placeholder);
+    BSON_ASSERT_PARAM(value_iter);
+    BSON_ASSERT(kb->crypt);
+    BSON_ASSERT(kb->crypt->opts.use_fle2_v2 == true);
+    BSON_ASSERT(placeholder->type == MONGOCRYPT_FLE2_PLACEHOLDER_TYPE_INSERT);
+
+    _mongocrypt_crypto_t *crypto = kb->crypt->crypto;
+    _mongocrypt_buffer_t value = {0};
+    bool res = false;
+
+    out->contentionFactor = 0; // k
+    if (placeholder->maxContentionCounter > 0) {
+        /* Choose a random contentionFactor in the inclusive range [0,
+         * placeholder->maxContentionCounter] */
+        if (!_mongocrypt_random_int64(crypto, placeholder->maxContentionCounter + 1, &out->contentionFactor, status)) {
+            goto fail;
+        }
+    }
+
+    _mongocrypt_buffer_from_iter(&value, value_iter);
+    if (!_mongocrypt_fle2_placeholder_common(kb,
+                                             common,
+                                             &placeholder->index_key_id,
+                                             &value,
+                                             true, /* derive tokens using counter */
+                                             out->contentionFactor,
+                                             status)) {
+        goto fail;
+    }
+
+    // d := EDCDerivedToken
+    _mongocrypt_buffer_steal(&out->edcDerivedToken, &common->edcDerivedToken);
+    // s := ESCDerivedToken
+    _mongocrypt_buffer_steal(&out->escDerivedToken, &common->escDerivedToken);
+    BSON_ASSERT(common->eccDerivedToken.data == NULL);
+
+    // p := EncryptCBC(ECOCToken, ESCDerivedFromDataTokenAndCounter)
+    if (!_fle2_derive_encrypted_token(crypto,
+                                      &out->encryptedTokens,
+                                      common->collectionsLevel1Token,
+                                      &out->escDerivedToken,
+                                      NULL, // unused in v2
+                                      status)) {
+        goto fail;
+    }
+
+    _mongocrypt_buffer_copy_to(&placeholder->index_key_id,
+                               &out->indexKeyId); // u
+    out->valueType = bson_iter_type(value_iter);  // t
+
+    // v := UserKeyId + EncryptCBCAEAD(UserKey, value)
+    {
+        _mongocrypt_buffer_t ciphertext = {0};
+        if (!_fle2_placeholder_aes_aead_encrypt(kb,
+                                                _mcFLE2v2AEADAlgorithm(),
+                                                &ciphertext,
+                                                &placeholder->user_key_id,
+                                                &value,
+                                                status)) {
+            goto fail;
+        }
+        const _mongocrypt_buffer_t v[2] = {placeholder->user_key_id, ciphertext};
+        const bool ok = _mongocrypt_buffer_concat(&out->value, v, 2);
+        _mongocrypt_buffer_cleanup(&ciphertext);
+        if (!ok) {
+            goto fail;
+        }
+    }
+
+    // e := ServerDataEncryptionLevel1Token
+    _mongocrypt_buffer_copy_to(mc_ServerDataEncryptionLevel1Token_get(common->serverDataEncryptionLevel1Token),
+                               &out->serverEncryptionToken);
+
+    // l := ServerDerivedFromDataToken
+    _mongocrypt_buffer_steal(&out->serverDerivedFromDataToken, &common->serverDerivedFromDataToken);
+
+    res = true;
+fail:
+    _mongocrypt_buffer_cleanup(&value);
+    return res;
+}
+
+/**
+ * Payload subtype 11: FLE2InsertUpdatePayloadV2
+ * Delegates to ..._insert_update_ciphertext_v1 for subtype 4
+ *   when crypt.opts.use_fle2_v2 == false
+ *
+ * {d: EDC, s: ESC, p: encToken,
+ *  u: indexKeyId, t: valueType, v: value,
+ *  e: serverToken, l: serverDerivedFromDataToken,
+ *  k: contentionFactor}
+ */
+static bool _mongocrypt_fle2_placeholder_to_insert_update_ciphertext(_mongocrypt_key_broker_t *kb,
+                                                                     _mongocrypt_marking_t *marking,
+                                                                     _mongocrypt_ciphertext_t *ciphertext,
+                                                                     mongocrypt_status_t *status) {
+    BSON_ASSERT_PARAM(kb);
+    BSON_ASSERT_PARAM(marking);
+    BSON_ASSERT_PARAM(ciphertext);
+    BSON_ASSERT(kb->crypt);
+    BSON_ASSERT(marking->type == MONGOCRYPT_MARKING_FLE2_ENCRYPTION);
+
+    if (!kb->crypt->opts.use_fle2_v2) {
+        return _mongocrypt_fle2_placeholder_to_insert_update_ciphertext_v1(kb, marking, ciphertext, status);
+    }
+
+    mc_FLE2EncryptionPlaceholder_t *placeholder = &marking->fle2;
+    _FLE2EncryptedPayloadCommon_t common = {{0}};
+    mc_FLE2InsertUpdatePayloadV2_t payload;
+    mc_FLE2InsertUpdatePayloadV2_init(&payload);
+    bool res = false;
+
+    if (!_mongocrypt_fle2_placeholder_to_insert_update_common(kb,
+                                                              &payload,
+                                                              &common,
+                                                              placeholder,
+                                                              &placeholder->v_iter,
+                                                              status)) {
+        goto fail;
+    }
+
+    {
+        bson_t out;
+        bson_init(&out);
+        mc_FLE2InsertUpdatePayloadV2_serialize(&payload, &out);
+        _mongocrypt_buffer_steal_from_bson(&ciphertext->data, &out);
+    }
+
+    // Do not set ciphertext->original_bson_type and ciphertext->key_id. They are
+    // not used for FLE2InsertUpdatePayloadV2.
+    ciphertext->blob_subtype = MC_SUBTYPE_FLE2InsertUpdatePayloadV2;
+
+    res = true;
+fail:
+    mc_FLE2InsertUpdatePayloadV2_cleanup(&payload);
+    _FLE2EncryptedPayloadCommon_cleanup(&common);
+
+    return res;
 }
 
 // get_edges creates and returns edges from an FLE2RangeInsertSpec. Returns NULL
 // on error.
-static mc_edges_t *
-get_edges (mc_FLE2RangeInsertSpec_t *insertSpec,
-           size_t sparsity,
-           mongocrypt_status_t *status)
-{
-   BSON_ASSERT_PARAM (insertSpec);
-
-   bson_type_t value_type = bson_iter_type (&insertSpec->v);
-
-
-   if (value_type == BSON_TYPE_INT32) {
-      return mc_getEdgesInt32 (
-         (mc_getEdgesInt32_args_t){
-            .value = bson_iter_int32 (&insertSpec->v),
-            .min = OPT_I32 (bson_iter_int32 (&insertSpec->min)),
-            .max = OPT_I32 (bson_iter_int32 (&insertSpec->max)),
-            .sparsity = sparsity},
-         status);
-   }
-
-   else if (value_type == BSON_TYPE_INT64) {
-      return mc_getEdgesInt64 (
-         (mc_getEdgesInt64_args_t){
-            .value = bson_iter_int64 (&insertSpec->v),
-            .min = OPT_I64 (bson_iter_int64 (&insertSpec->min)),
-            .max = OPT_I64 (bson_iter_int64 (&insertSpec->max)),
-            .sparsity = sparsity},
-         status);
-   }
-
-   else if (value_type == BSON_TYPE_DATE_TIME) {
-      return mc_getEdgesInt64 (
-         (mc_getEdgesInt64_args_t){
-            .value = bson_iter_date_time (&insertSpec->v),
-            .min = OPT_I64 (bson_iter_date_time (&insertSpec->min)),
-            .max = OPT_I64 (bson_iter_date_time (&insertSpec->max)),
-            .sparsity = sparsity},
-         status);
-   }
-
-   else if (value_type == BSON_TYPE_DOUBLE) {
-      mc_getEdgesDouble_args_t args = {
-         .value = bson_iter_double (&insertSpec->v), .sparsity = sparsity};
-      if (insertSpec->precision.set) {
-         // If precision is set, pass min/max/precision to mc_getEdgesDouble.
-         // Do not pass min/max if precision is not set. All three must be set
-         // or all three must be unset in mc_getTypeInfoDouble.
-         args.min = OPT_DOUBLE (bson_iter_double (&insertSpec->min));
-         args.max = OPT_DOUBLE (bson_iter_double (&insertSpec->max));
-         args.precision = insertSpec->precision;
-      }
-
-      return mc_getEdgesDouble (args, status);
-   }
-
-   else if (value_type == BSON_TYPE_DECIMAL128) {
+static mc_edges_t *get_edges(mc_FLE2RangeInsertSpec_t *insertSpec, size_t sparsity, mongocrypt_status_t *status) {
+    BSON_ASSERT_PARAM(insertSpec);
+
+    bson_type_t value_type = bson_iter_type(&insertSpec->v);
+
+    if (value_type == BSON_TYPE_INT32) {
+        return mc_getEdgesInt32((mc_getEdgesInt32_args_t){.value = bson_iter_int32(&insertSpec->v),
+                                                          .min = OPT_I32(bson_iter_int32(&insertSpec->min)),
+                                                          .max = OPT_I32(bson_iter_int32(&insertSpec->max)),
+                                                          .sparsity = sparsity},
+                                status);
+    }
+
+    else if (value_type == BSON_TYPE_INT64) {
+        return mc_getEdgesInt64((mc_getEdgesInt64_args_t){.value = bson_iter_int64(&insertSpec->v),
+                                                          .min = OPT_I64(bson_iter_int64(&insertSpec->min)),
+                                                          .max = OPT_I64(bson_iter_int64(&insertSpec->max)),
+                                                          .sparsity = sparsity},
+                                status);
+    }
+
+    else if (value_type == BSON_TYPE_DATE_TIME) {
+        return mc_getEdgesInt64((mc_getEdgesInt64_args_t){.value = bson_iter_date_time(&insertSpec->v),
+                                                          .min = OPT_I64(bson_iter_date_time(&insertSpec->min)),
+                                                          .max = OPT_I64(bson_iter_date_time(&insertSpec->max)),
+                                                          .sparsity = sparsity},
+                                status);
+    }
+
+    else if (value_type == BSON_TYPE_DOUBLE) {
+        mc_getEdgesDouble_args_t args = {.value = bson_iter_double(&insertSpec->v), .sparsity = sparsity};
+        if (insertSpec->precision.set) {
+            // If precision is set, pass min/max/precision to mc_getEdgesDouble.
+            // Do not pass min/max if precision is not set. All three must be set
+            // or all three must be unset in mc_getTypeInfoDouble.
+            args.min = OPT_DOUBLE(bson_iter_double(&insertSpec->min));
+            args.max = OPT_DOUBLE(bson_iter_double(&insertSpec->max));
+            args.precision = insertSpec->precision;
+        }
+
+        return mc_getEdgesDouble(args, status);
+    }
+
+    else if (value_type == BSON_TYPE_DECIMAL128) {
 #if MONGOCRYPT_HAVE_DECIMAL128_SUPPORT
-      const mc_dec128 value = mc_dec128_from_bson_iter (&insertSpec->v);
-      mc_getEdgesDecimal128_args_t args = {
-         .value = value,
-         .sparsity = sparsity,
-      };
-      if (insertSpec->precision.set) {
-         const mc_dec128 min = mc_dec128_from_bson_iter (&insertSpec->min);
-         const mc_dec128 max = mc_dec128_from_bson_iter (&insertSpec->max);
-         args.min = OPT_MC_DEC128 (min);
-         args.max = OPT_MC_DEC128 (max);
-         args.precision = insertSpec->precision;
-      }
-      return mc_getEdgesDecimal128 (args, status);
+        const mc_dec128 value = mc_dec128_from_bson_iter(&insertSpec->v);
+        mc_getEdgesDecimal128_args_t args = {
+            .value = value,
+            .sparsity = sparsity,
+        };
+        if (insertSpec->precision.set) {
+            const mc_dec128 min = mc_dec128_from_bson_iter(&insertSpec->min);
+            const mc_dec128 max = mc_dec128_from_bson_iter(&insertSpec->max);
+            args.min = OPT_MC_DEC128(min);
+            args.max = OPT_MC_DEC128(max);
+            args.precision = insertSpec->precision;
+        }
+        return mc_getEdgesDecimal128(args, status);
 #else // ↑↑↑↑↑↑↑↑ With Decimal128 / Without ↓↓↓↓↓↓↓↓↓↓
-      CLIENT_ERR ("unsupported BSON type (Decimal128) for range: libmongocrypt "
-                  "was built without extended Decimal128 support");
-      return NULL;
+        CLIENT_ERR("unsupported BSON type (Decimal128) for range: libmongocrypt "
+                   "was built without extended Decimal128 support");
+        return NULL;
 #endif
-   }
+    }
 
-
-   CLIENT_ERR ("unsupported BSON type: %s for range",
-               mc_bson_type_to_string (value_type));
-   return NULL;
+    CLIENT_ERR("unsupported BSON type: %s for range", mc_bson_type_to_string(value_type));
+    return NULL;
 }
 
-// _mongocrypt_fle2_placeholder_to_insert_update_ciphertextForRange transforms a
-// FLE2EncryptedPlaceholder to an FLE2InsertUpdatePayload for the range
-// algorithm.
-static bool
-_mongocrypt_fle2_placeholder_to_insert_update_ciphertextForRange (
-   _mongocrypt_key_broker_t *kb,
-   _mongocrypt_marking_t *marking,
-   _mongocrypt_ciphertext_t *ciphertext,
-   mongocrypt_status_t *status)
-{
-   BSON_ASSERT_PARAM (kb);
-   BSON_ASSERT_PARAM (marking);
-   BSON_ASSERT_PARAM (ciphertext);
-   BSON_ASSERT (kb->crypt);
-
-   _mongocrypt_crypto_t *crypto = kb->crypt->crypto;
-   _FLE2EncryptedPayloadCommon_t common = {{0}};
-   _mongocrypt_buffer_t value = {0};
-   mc_FLE2EncryptionPlaceholder_t *placeholder = &marking->fle2;
-   mc_FLE2InsertUpdatePayload_t payload;
-   bool res = false;
-   mc_edges_t *edges = NULL;
-
-   BSON_ASSERT (marking->type == MONGOCRYPT_MARKING_FLE2_ENCRYPTION);
-   BSON_ASSERT (placeholder->type == MONGOCRYPT_FLE2_PLACEHOLDER_TYPE_INSERT);
-   BSON_ASSERT (placeholder->algorithm == MONGOCRYPT_FLE2_ALGORITHM_RANGE);
-   _mongocrypt_ciphertext_init (ciphertext);
-   mc_FLE2InsertUpdatePayload_init (&payload);
-
-   // Parse the value ("v"), min ("min"), and max ("max") from
-   // FLE2EncryptionPlaceholder for range insert.
-   mc_FLE2RangeInsertSpec_t insertSpec;
-   if (!mc_FLE2RangeInsertSpec_parse (
-          &insertSpec, &placeholder->v_iter, status)) {
-      goto fail;
-   }
-
-   _mongocrypt_buffer_from_iter (&value, &insertSpec.v);
-
-   int64_t contentionFactor = 0;
-   if (placeholder->maxContentionCounter > 0) {
-      /* Choose a random contentionFactor in the inclusive range [0,
-       * placeholder->maxContentionCounter] */
-      if (!_mongocrypt_random_int64 (crypto,
-                                     placeholder->maxContentionCounter + 1,
-                                     &contentionFactor,
-                                     status)) {
-         goto fail;
-      }
-   }
-
-   if (!_mongocrypt_fle2_placeholder_common (
-          kb,
-          &common,
-          &placeholder->index_key_id,
-          &value,
-          true, /* derive tokens using counter */
-          contentionFactor,
-          status)) {
-      goto fail;
-   }
-
-   // d := EDCDerivedToken
-   _mongocrypt_buffer_steal (&payload.edcDerivedToken, &common.edcDerivedToken);
-   // s := ESCDerivedToken
-   _mongocrypt_buffer_steal (&payload.escDerivedToken, &common.escDerivedToken);
-   // c := ECCDerivedToken
-   _mongocrypt_buffer_steal (&payload.eccDerivedToken, &common.eccDerivedToken);
-
-   // p := EncryptCTR(ECOCToken, ESCDerivedFromDataTokenAndCounter ||
-   // ECCDerivedFromDataTokenAndCounter)
-   {
-      _mongocrypt_buffer_t tokens[] = {payload.escDerivedToken,
-                                       payload.eccDerivedToken};
-      _mongocrypt_buffer_t p;
-      _mongocrypt_buffer_concat (&p, tokens, 2);
-      mc_ECOCToken_t *ecocToken =
-         mc_ECOCToken_new (crypto, common.collectionsLevel1Token, status);
-      if (!ecocToken) {
-         _mongocrypt_buffer_cleanup (&p);
-         goto fail;
-      }
-      bool ok = _fle2_placeholder_aes_ctr_encrypt (kb,
-                                                   mc_ECOCToken_get (ecocToken),
-                                                   &p,
-                                                   &payload.encryptedTokens,
-                                                   status);
-      _mongocrypt_buffer_cleanup (&p);
-      mc_ECOCToken_destroy (ecocToken);
-      if (!ok) {
-         goto fail;
-      }
-   }
-
-   _mongocrypt_buffer_copy_to (&placeholder->index_key_id,
-                               &payload.indexKeyId);   // u
-   payload.valueType = bson_iter_type (&insertSpec.v); // t
-
-   // v := UserKeyId + EncryptAEAD(UserKey, value)
-   {
-      _mongocrypt_buffer_t tmp[2] = {placeholder->user_key_id, {0}};
-      if (!_fle2_placeholder_aead_encrypt (
-             kb, &placeholder->user_key_id, &value, &tmp[1], status)) {
-         goto fail;
-      }
-      bool ok = _mongocrypt_buffer_concat (&payload.value, tmp, 2);
-      _mongocrypt_buffer_cleanup (&tmp[1]);
-      if (!ok) {
-         goto fail;
-      }
-   }
-
-   // e := ServerDataEncryptionLevel1Token
-   {
-      mc_ServerDataEncryptionLevel1Token_t *serverToken =
-         mc_ServerDataEncryptionLevel1Token_new (
-            crypto, &common.tokenKey, status);
-      if (!serverToken) {
-         goto fail;
-      }
-      _mongocrypt_buffer_copy_to (
-         mc_ServerDataEncryptionLevel1Token_get (serverToken),
-         &payload.serverEncryptionToken);
-      mc_ServerDataEncryptionLevel1Token_destroy (serverToken);
-   }
-
-   // g:= array<EdgeTokenSet>
-   {
-      BSON_ASSERT (placeholder->sparsity >= 0 &&
-                   (uint64_t) placeholder->sparsity <= (uint64_t) SIZE_MAX);
-      edges = get_edges (&insertSpec, (size_t) placeholder->sparsity, status);
-      if (!edges) {
-         goto fail;
-      }
-
-      for (size_t i = 0; i < mc_edges_len (edges); i++) {
-         // Create an EdgeTokenSet from each edge.
-         bool loop_ok = false;
-         const char *edge = mc_edges_get (edges, i);
-         _mongocrypt_buffer_t edge_buf = {0};
-         _FLE2EncryptedPayloadCommon_t edge_tokens = {{0}};
-         _mongocrypt_buffer_t encryptedTokens = {0};
-         mc_EdgeTokenSet_t etc = {{0}};
-
-         if (!_mongocrypt_buffer_from_string (&edge_buf, edge)) {
-            CLIENT_ERR ("failed to copy edge to buffer");
-            goto fail_loop;
-         }
-
-         if (!_mongocrypt_fle2_placeholder_common (
-                kb,
-                &edge_tokens,
-                &placeholder->index_key_id,
-                &edge_buf,
-                true, /* derive tokens using counter */
-                contentionFactor,
-                status)) {
-            goto fail_loop;
-         }
-
-         // p := EncryptCTR(ECOCToken, ESCDerivedFromDataTokenAndCounter ||
-         // ECCDerivedFromDataTokenAndCounter)
-         {
-            _mongocrypt_buffer_t tokens[] = {edge_tokens.escDerivedToken,
-                                             edge_tokens.eccDerivedToken};
-            _mongocrypt_buffer_t p;
-            _mongocrypt_buffer_concat (&p, tokens, 2);
-            mc_ECOCToken_t *ecocToken = mc_ECOCToken_new (
-               crypto, edge_tokens.collectionsLevel1Token, status);
-            if (!ecocToken) {
-               _mongocrypt_buffer_cleanup (&p);
-               goto fail_loop;
+/**
+ * Payload subtype 4: FLE2InsertUpdatePayload for range updates
+ *
+ * {d: EDC, s: ESC, c: ECC,
+ *  p: encToken, u: indexKeyId, t: type,
+ *  v: value, e: serverToken,
+ *  g: [{d: EDC, s: ESC, c: ECC, p: encToken},
+ *      {d: EDC, s: ESC, c: ECC, p: encToken},
+ *      ...]}
+ */
+static bool _mongocrypt_fle2_placeholder_to_insert_update_ciphertextForRange_v1(_mongocrypt_key_broker_t *kb,
+                                                                                _mongocrypt_marking_t *marking,
+                                                                                _mongocrypt_ciphertext_t *ciphertext,
+                                                                                mongocrypt_status_t *status) {
+    BSON_ASSERT_PARAM(kb);
+    BSON_ASSERT_PARAM(marking);
+    BSON_ASSERT_PARAM(ciphertext);
+    BSON_ASSERT_PARAM(status);
+    BSON_ASSERT(kb->crypt);
+    BSON_ASSERT(kb->crypt->opts.use_fle2_v2 == false);
+    BSON_ASSERT(marking->type == MONGOCRYPT_MARKING_FLE2_ENCRYPTION);
+    BSON_ASSERT(marking->fle2.algorithm == MONGOCRYPT_FLE2_ALGORITHM_RANGE);
+
+    mc_FLE2EncryptionPlaceholder_t *placeholder = &marking->fle2;
+    _FLE2EncryptedPayloadCommon_t common = {{0}};
+    mc_FLE2InsertUpdatePayload_t payload;
+    mc_FLE2InsertUpdatePayload_init(&payload);
+    bool res = false;
+    mc_edges_t *edges = NULL;
+
+    // Parse the value ("v"), min ("min"), and max ("max") from
+    // FLE2EncryptionPlaceholder for range insert.
+    mc_FLE2RangeInsertSpec_t insertSpec;
+    if (!mc_FLE2RangeInsertSpec_parse(&insertSpec, &placeholder->v_iter, status)) {
+        goto fail;
+    }
+
+    int64_t contentionFactor = 0;
+    if (!_mongocrypt_fle2_placeholder_to_insert_update_common_v1(kb,
+                                                                 &payload,
+                                                                 &contentionFactor,
+                                                                 &common,
+                                                                 &marking->fle2,
+                                                                 &insertSpec.v,
+                                                                 status)) {
+        goto fail;
+    }
+
+    // g:= array<EdgeTokenSet>
+    {
+        BSON_ASSERT(placeholder->sparsity >= 0 && (uint64_t)placeholder->sparsity <= (uint64_t)SIZE_MAX);
+        edges = get_edges(&insertSpec, (size_t)placeholder->sparsity, status);
+        if (!edges) {
+            goto fail;
+        }
+
+        for (size_t i = 0; i < mc_edges_len(edges); ++i) {
+            // Create an EdgeTokenSet from each edge.
+            bool loop_ok = false;
+            const char *edge = mc_edges_get(edges, i);
+            _mongocrypt_buffer_t edge_buf = {0};
+            _FLE2EncryptedPayloadCommon_t edge_tokens = {{0}};
+            _mongocrypt_buffer_t encryptedTokens = {0};
+            mc_EdgeTokenSet_t etc = {{0}};
+
+            if (!_mongocrypt_buffer_from_string(&edge_buf, edge)) {
+                CLIENT_ERR("failed to copy edge to buffer");
+                goto fail_loop;
             }
-            bool ok = _fle2_placeholder_aes_ctr_encrypt (
-               kb, mc_ECOCToken_get (ecocToken), &p, &encryptedTokens, status);
-            _mongocrypt_buffer_cleanup (&p);
-            mc_ECOCToken_destroy (ecocToken);
-            if (!ok) {
-               goto fail_loop;
+
+            if (!_mongocrypt_fle2_placeholder_common(kb,
+                                                     &edge_tokens,
+                                                     &placeholder->index_key_id,
+                                                     &edge_buf,
+                                                     true, /* derive tokens using counter */
+                                                     contentionFactor,
+                                                     status)) {
+                goto fail_loop;
             }
-         }
-
-         // d := EDCDerivedToken
-         _mongocrypt_buffer_steal (&etc.edcDerivedToken,
-                                   &edge_tokens.edcDerivedToken);
-         // s := ESCDerivedToken
-         _mongocrypt_buffer_steal (&etc.escDerivedToken,
-                                   &edge_tokens.escDerivedToken);
-         // c := ECCDerivedToken
-         _mongocrypt_buffer_steal (&etc.eccDerivedToken,
-                                   &edge_tokens.eccDerivedToken);
-
-         _mongocrypt_buffer_steal (&etc.encryptedTokens, &encryptedTokens);
-         _mc_array_append_val (&payload.edgeTokenSetArray, etc);
-
-         loop_ok = true;
-      fail_loop:
-         _mongocrypt_buffer_cleanup (&encryptedTokens);
-         _FLE2EncryptedPayloadCommon_cleanup (&edge_tokens);
-         _mongocrypt_buffer_cleanup (&edge_buf);
-         if (!loop_ok) {
+
+            // d := EDCDerivedToken
+            _mongocrypt_buffer_steal(&etc.edcDerivedToken, &edge_tokens.edcDerivedToken);
+            // s := ESCDerivedToken
+            _mongocrypt_buffer_steal(&etc.escDerivedToken, &edge_tokens.escDerivedToken);
+            // c := ECCDerivedToken
+            _mongocrypt_buffer_steal(&etc.eccDerivedToken, &edge_tokens.eccDerivedToken);
+
+            // p := EncryptCTR(ECOCToken, ESCDerivedFromDataTokenAndCounter ||
+            // ECCDerivedFromDataTokenAndCounter)
+            if (!_fle2_derive_encrypted_token(kb->crypt->crypto,
+                                              &etc.encryptedTokens,
+                                              edge_tokens.collectionsLevel1Token,
+                                              &etc.escDerivedToken,
+                                              &etc.eccDerivedToken,
+                                              status)) {
+                goto fail_loop;
+            }
+
+            _mc_array_append_val(&payload.edgeTokenSetArray, etc);
+
+            loop_ok = true;
+        fail_loop:
+            _mongocrypt_buffer_cleanup(&encryptedTokens);
+            _FLE2EncryptedPayloadCommon_cleanup(&edge_tokens);
+            _mongocrypt_buffer_cleanup(&edge_buf);
+            if (!loop_ok) {
+                goto fail;
+            }
+        }
+    }
+
+    {
+        bson_t out;
+        bson_init(&out);
+        mc_FLE2InsertUpdatePayload_serializeForRange(&payload, &out);
+        _mongocrypt_buffer_steal_from_bson(&ciphertext->data, &out);
+    }
+    // Do not set ciphertext->original_bson_type and ciphertext->key_id. They are
+    // not used for FLE2InsertUpdatePayload.
+    ciphertext->blob_subtype = MC_SUBTYPE_FLE2InsertUpdatePayload;
+
+    res = true;
+fail:
+    mc_edges_destroy(edges);
+    mc_FLE2InsertUpdatePayload_cleanup(&payload);
+    _FLE2EncryptedPayloadCommon_cleanup(&common);
+
+    return res;
+}
+
+/**
+ * Payload subtype 11: FLE2InsertUpdatePayloadV2 for range updates
+ * Delegates to ..._insert_update_ciphertextForRange_v1 for subtype 4
+ *   when crypt.opts.use_fle2_v2 == false
+ *
+ * {d: EDC, s: ESC, p: encToken,
+ *  u: indexKeyId, t: valueType, v: value,
+ *  e: serverToken, l: serverDerivedFromDataToken,
+ *  k: contentionFactor,
+ *  g: [{d: EDC, s: ESC, l: serverDerivedFromDataToken, p: encToken},
+ *      {d: EDC, s: ESC, l: serverDerivedFromDataToken, p: encToken},
+ *      ...]}
+ */
+static bool _mongocrypt_fle2_placeholder_to_insert_update_ciphertextForRange(_mongocrypt_key_broker_t *kb,
+                                                                             _mongocrypt_marking_t *marking,
+                                                                             _mongocrypt_ciphertext_t *ciphertext,
+                                                                             mongocrypt_status_t *status) {
+    BSON_ASSERT_PARAM(kb);
+    BSON_ASSERT_PARAM(marking);
+    BSON_ASSERT_PARAM(ciphertext);
+    BSON_ASSERT(kb->crypt);
+    BSON_ASSERT(marking->type == MONGOCRYPT_MARKING_FLE2_ENCRYPTION);
+
+    if (!kb->crypt->opts.use_fle2_v2) {
+        return _mongocrypt_fle2_placeholder_to_insert_update_ciphertextForRange_v1(kb, marking, ciphertext, status);
+    }
+
+    mc_FLE2EncryptionPlaceholder_t *placeholder = &marking->fle2;
+    _FLE2EncryptedPayloadCommon_t common = {{0}};
+    mc_FLE2InsertUpdatePayloadV2_t payload;
+    mc_FLE2InsertUpdatePayloadV2_init(&payload);
+    bool res = false;
+    mc_edges_t *edges = NULL;
+
+    // Parse the value ("v"), min ("min"), and max ("max") from
+    // FLE2EncryptionPlaceholder for range insert.
+    mc_FLE2RangeInsertSpec_t insertSpec;
+    if (!mc_FLE2RangeInsertSpec_parse(&insertSpec, &placeholder->v_iter, status)) {
+        goto fail;
+    }
+
+    if (!_mongocrypt_fle2_placeholder_to_insert_update_common(kb,
+                                                              &payload,
+                                                              &common,
+                                                              &marking->fle2,
+                                                              &insertSpec.v,
+                                                              status)) {
+        goto fail;
+    }
+
+    // g:= array<EdgeTokenSetV2>
+    {
+        BSON_ASSERT(placeholder->sparsity >= 0 && (uint64_t)placeholder->sparsity <= (uint64_t)SIZE_MAX);
+        edges = get_edges(&insertSpec, (size_t)placeholder->sparsity, status);
+        if (!edges) {
             goto fail;
-         }
-      }
-   }
-
-   // Serialize.
-   {
-      bson_t out;
-      bson_init (&out);
-      mc_FLE2InsertUpdatePayload_serializeForRange (&payload, &out);
-      _mongocrypt_buffer_steal_from_bson (&ciphertext->data, &out);
-   }
-   // Do not set ciphertext->original_bson_type and ciphertext->key_id. They are
-   // not used for FLE2InsertUpdatePayload.
-   ciphertext->blob_subtype = MC_SUBTYPE_FLE2InsertUpdatePayload;
-
-   res = true;
+        }
+
+        for (size_t i = 0; i < mc_edges_len(edges); ++i) {
+            // Create an EdgeTokenSet from each edge.
+            bool loop_ok = false;
+            const char *edge = mc_edges_get(edges, i);
+            _mongocrypt_buffer_t edge_buf = {0};
+            _FLE2EncryptedPayloadCommon_t edge_tokens = {{0}};
+            _mongocrypt_buffer_t encryptedTokens = {0};
+            mc_EdgeTokenSetV2_t etc = {{0}};
+
+            if (!_mongocrypt_buffer_from_string(&edge_buf, edge)) {
+                CLIENT_ERR("failed to copy edge to buffer");
+                goto fail_loop;
+            }
+
+            if (!_mongocrypt_fle2_placeholder_common(kb,
+                                                     &edge_tokens,
+                                                     &placeholder->index_key_id,
+                                                     &edge_buf,
+                                                     true, /* derive tokens using counter */
+                                                     payload.contentionFactor,
+                                                     status)) {
+                goto fail_loop;
+            }
+            BSON_ASSERT(edge_tokens.eccDerivedToken.data == NULL);
+
+            // d := EDCDerivedToken
+            _mongocrypt_buffer_steal(&etc.edcDerivedToken, &edge_tokens.edcDerivedToken);
+            // s := ESCDerivedToken
+            _mongocrypt_buffer_steal(&etc.escDerivedToken, &edge_tokens.escDerivedToken);
+
+            // l := serverDerivedFromDataToken
+            _mongocrypt_buffer_steal(&etc.serverDerivedFromDataToken, &edge_tokens.serverDerivedFromDataToken);
+
+            // p := EncryptCBC(ECOCToken, ESCDerivedFromDataTokenAndCounter)
+            if (!_fle2_derive_encrypted_token(kb->crypt->crypto,
+                                              &etc.encryptedTokens,
+                                              edge_tokens.collectionsLevel1Token,
+                                              &etc.escDerivedToken,
+                                              NULL, // ecc unsed in FLE2v2
+                                              status)) {
+                goto fail_loop;
+            }
+
+            _mc_array_append_val(&payload.edgeTokenSetArray, etc);
+
+            loop_ok = true;
+        fail_loop:
+            _mongocrypt_buffer_cleanup(&encryptedTokens);
+            _FLE2EncryptedPayloadCommon_cleanup(&edge_tokens);
+            _mongocrypt_buffer_cleanup(&edge_buf);
+            if (!loop_ok) {
+                goto fail;
+            }
+        }
+    }
+
+    {
+        bson_t out;
+        bson_init(&out);
+        mc_FLE2InsertUpdatePayloadV2_serializeForRange(&payload, &out);
+        _mongocrypt_buffer_steal_from_bson(&ciphertext->data, &out);
+    }
+    // Do not set ciphertext->original_bson_type and ciphertext->key_id. They are
+    // not used for FLE2InsertUpdatePayloadV2.
+    ciphertext->blob_subtype = MC_SUBTYPE_FLE2InsertUpdatePayloadV2;
+
+    res = true;
 fail:
-   mc_edges_destroy (edges);
-   mc_FLE2InsertUpdatePayload_cleanup (&payload);
-   _mongocrypt_buffer_cleanup (&value);
-   _FLE2EncryptedPayloadCommon_cleanup (&common);
+    mc_edges_destroy(edges);
+    mc_FLE2InsertUpdatePayloadV2_cleanup(&payload);
+    _FLE2EncryptedPayloadCommon_cleanup(&common);
 
-   return res;
+    return res;
 }
 
+/**
+ * Payload subtype 5: FLE2FindEqualityPayload
+ *
+ * {d: EDC, s: ESC, c: ECC, e: serverToken, cm: contentionCounter}
+ */
+static bool _mongocrypt_fle2_placeholder_to_find_ciphertext_v1(_mongocrypt_key_broker_t *kb,
+                                                               _mongocrypt_marking_t *marking,
+                                                               _mongocrypt_ciphertext_t *ciphertext,
+                                                               mongocrypt_status_t *status) {
+    BSON_ASSERT_PARAM(kb);
+    BSON_ASSERT_PARAM(marking);
+    BSON_ASSERT_PARAM(ciphertext);
+
+    _FLE2EncryptedPayloadCommon_t common = {{0}};
+    _mongocrypt_buffer_t value = {0};
+    mc_FLE2EncryptionPlaceholder_t *placeholder = &marking->fle2;
+    mc_FLE2FindEqualityPayload_t payload;
+    bool res = false;
+
+    BSON_ASSERT(kb->crypt->opts.use_fle2_v2 == false);
+    BSON_ASSERT(marking->type == MONGOCRYPT_MARKING_FLE2_ENCRYPTION);
+    BSON_ASSERT(placeholder->type == MONGOCRYPT_FLE2_PLACEHOLDER_TYPE_FIND);
+    _mongocrypt_buffer_init(&value);
+    mc_FLE2FindEqualityPayload_init(&payload);
+
+    _mongocrypt_buffer_from_iter(&value, &placeholder->v_iter);
+
+    if (!_mongocrypt_fle2_placeholder_common(kb,
+                                             &common,
+                                             &placeholder->index_key_id,
+                                             &value,
+                                             false, /* derive tokens without counter */
+                                             placeholder->maxContentionCounter,
+                                             status)) {
+        goto fail;
+    }
+
+    // d := EDCDerivedToken
+    _mongocrypt_buffer_steal(&payload.edcDerivedToken, &common.edcDerivedToken);
+    // s := ESCDerivedToken
+    _mongocrypt_buffer_steal(&payload.escDerivedToken, &common.escDerivedToken);
+    // c := ECCDerivedToken
+    _mongocrypt_buffer_steal(&payload.eccDerivedToken, &common.eccDerivedToken);
+
+    // e := ServerDataEncryptionLevel1Token
+    _mongocrypt_buffer_copy_to(mc_ServerDataEncryptionLevel1Token_get(common.serverDataEncryptionLevel1Token),
+                               &payload.serverEncryptionToken);
+
+    payload.maxContentionCounter = placeholder->maxContentionCounter;
+
+    {
+        bson_t out;
+        bson_init(&out);
+        mc_FLE2FindEqualityPayload_serialize(&payload, &out);
+        _mongocrypt_buffer_steal_from_bson(&ciphertext->data, &out);
+    }
+    // Do not set ciphertext->original_bson_type and ciphertext->key_id. They are
+    // not used for FLE2FindEqualityPayload.
+    ciphertext->blob_subtype = MC_SUBTYPE_FLE2FindEqualityPayload;
+
+    res = true;
+fail:
+    mc_FLE2FindEqualityPayload_cleanup(&payload);
+    _mongocrypt_buffer_cleanup(&value);
+    _FLE2EncryptedPayloadCommon_cleanup(&common);
 
-static bool
-_mongocrypt_fle2_placeholder_to_find_ciphertext (
-   _mongocrypt_key_broker_t *kb,
-   _mongocrypt_marking_t *marking,
-   _mongocrypt_ciphertext_t *ciphertext,
-   mongocrypt_status_t *status)
-{
-   BSON_ASSERT_PARAM (kb);
-   BSON_ASSERT_PARAM (marking);
-   BSON_ASSERT_PARAM (ciphertext);
-
-   _FLE2EncryptedPayloadCommon_t common = {{0}};
-   _mongocrypt_buffer_t value = {0};
-   mc_FLE2EncryptionPlaceholder_t *placeholder = &marking->fle2;
-   mc_FLE2FindEqualityPayload_t payload;
-   bool res = false;
-
-   BSON_ASSERT (marking->type == MONGOCRYPT_MARKING_FLE2_ENCRYPTION);
-   BSON_ASSERT (placeholder->type == MONGOCRYPT_FLE2_PLACEHOLDER_TYPE_FIND);
-   _mongocrypt_ciphertext_init (ciphertext);
-   _mongocrypt_buffer_init (&value);
-   mc_FLE2FindEqualityPayload_init (&payload);
-
-   _mongocrypt_buffer_from_iter (&value, &placeholder->v_iter);
-
-   if (!_mongocrypt_fle2_placeholder_common (
-          kb,
-          &common,
-          &placeholder->index_key_id,
-          &value,
-          false, /* derive tokens without counter */
-          placeholder->maxContentionCounter,
-          status)) {
-      goto fail;
-   }
-
-   // d := EDCDerivedToken
-   _mongocrypt_buffer_steal (&payload.edcDerivedToken, &common.edcDerivedToken);
-   // s := ESCDerivedToken
-   _mongocrypt_buffer_steal (&payload.escDerivedToken, &common.escDerivedToken);
-   // c := ECCDerivedToken
-   _mongocrypt_buffer_steal (&payload.eccDerivedToken, &common.eccDerivedToken);
-
-   // e := ServerDataEncryptionLevel1Token
-   BSON_ASSERT (kb->crypt);
-   {
-      mc_ServerDataEncryptionLevel1Token_t *serverToken =
-         mc_ServerDataEncryptionLevel1Token_new (
-            kb->crypt->crypto, &common.tokenKey, status);
-      if (!serverToken) {
-         goto fail;
-      }
-      _mongocrypt_buffer_copy_to (
-         mc_ServerDataEncryptionLevel1Token_get (serverToken),
-         &payload.serverEncryptionToken);
-      mc_ServerDataEncryptionLevel1Token_destroy (serverToken);
-   }
-
-   payload.maxContentionCounter = placeholder->maxContentionCounter;
-
-   {
-      bson_t out;
-      bson_init (&out);
-      mc_FLE2FindEqualityPayload_serialize (&payload, &out);
-      _mongocrypt_buffer_steal_from_bson (&ciphertext->data, &out);
-   }
-   // Do not set ciphertext->original_bson_type and ciphertext->key_id. They are
-   // not used for FLE2FindEqualityPayload.
-   ciphertext->blob_subtype = MC_SUBTYPE_FLE2FindEqualityPayload;
-
-   res = true;
+    return res;
+}
+
+/**
+ * Payload subtype 12: FLE2FindEqualityPayloadV2
+ * Delegates to ..._find_ciphertext_v1 when crypt->opts.use_fle2_v2 == false.
+ *
+ * {d: EDC, s: ESC, l: serverDerivedFromDataToken, cm: contentionCounter}
+ */
+static bool _mongocrypt_fle2_placeholder_to_find_ciphertext(_mongocrypt_key_broker_t *kb,
+                                                            _mongocrypt_marking_t *marking,
+                                                            _mongocrypt_ciphertext_t *ciphertext,
+                                                            mongocrypt_status_t *status) {
+    BSON_ASSERT_PARAM(kb);
+    BSON_ASSERT_PARAM(marking);
+    BSON_ASSERT_PARAM(ciphertext);
+
+    if (kb->crypt->opts.use_fle2_v2 == false) {
+        return _mongocrypt_fle2_placeholder_to_find_ciphertext_v1(kb, marking, ciphertext, status);
+    }
+
+    _FLE2EncryptedPayloadCommon_t common = {{0}};
+    _mongocrypt_buffer_t value = {0};
+    mc_FLE2EncryptionPlaceholder_t *placeholder = &marking->fle2;
+    mc_FLE2FindEqualityPayloadV2_t payload;
+    bool res = false;
+
+    BSON_ASSERT(marking->type == MONGOCRYPT_MARKING_FLE2_ENCRYPTION);
+    BSON_ASSERT(placeholder->type == MONGOCRYPT_FLE2_PLACEHOLDER_TYPE_FIND);
+
+    _mongocrypt_buffer_init(&value);
+    mc_FLE2FindEqualityPayloadV2_init(&payload);
+
+    _mongocrypt_buffer_from_iter(&value, &placeholder->v_iter);
+
+    if (!_mongocrypt_fle2_placeholder_common(kb,
+                                             &common,
+                                             &placeholder->index_key_id,
+                                             &value,
+                                             false, /* derive tokens without counter */
+                                             placeholder->maxContentionCounter,
+                                             status)) {
+        goto fail;
+    }
+    BSON_ASSERT(common.eccDerivedToken.data == NULL);
+
+    // d := EDCDerivedToken
+    _mongocrypt_buffer_steal(&payload.edcDerivedToken, &common.edcDerivedToken);
+    // s := ESCDerivedToken
+    _mongocrypt_buffer_steal(&payload.escDerivedToken, &common.escDerivedToken);
+    // l := serverDerivedFromDataToken
+    _mongocrypt_buffer_steal(&payload.serverDerivedFromDataToken, &common.serverDerivedFromDataToken);
+
+    // cm := maxContentionCounter
+    payload.maxContentionCounter = placeholder->maxContentionCounter;
+
+    {
+        bson_t out;
+        bson_init(&out);
+        mc_FLE2FindEqualityPayloadV2_serialize(&payload, &out);
+        _mongocrypt_buffer_steal_from_bson(&ciphertext->data, &out);
+    }
+    // Do not set ciphertext->original_bson_type and ciphertext->key_id. They are
+    // not used for FLE2FindEqualityPayloadV2.
+    ciphertext->blob_subtype = MC_SUBTYPE_FLE2FindEqualityPayloadV2;
+
+    res = true;
 fail:
-   mc_FLE2FindEqualityPayload_cleanup (&payload);
-   _mongocrypt_buffer_cleanup (&value);
-   _FLE2EncryptedPayloadCommon_cleanup (&common);
+    mc_FLE2FindEqualityPayloadV2_cleanup(&payload);
+    _mongocrypt_buffer_cleanup(&value);
+    _FLE2EncryptedPayloadCommon_cleanup(&common);
 
-   return res;
+    return res;
 }
 
-static bool
-isInfinite (bson_iter_t *iter)
-{
-   return mc_isinf (bson_iter_double (iter));
+static bool isInfinite(bson_iter_t *iter) {
+    return mc_isinf(bson_iter_double(iter));
 }
 
 // mc_get_mincover_from_FLE2RangeFindSpec creates and returns a mincover from an
 // FLE2RangeFindSpec. Returns NULL on error.
 mc_mincover_t *
-mc_get_mincover_from_FLE2RangeFindSpec (mc_FLE2RangeFindSpec_t *findSpec,
-                                        size_t sparsity,
-                                        mongocrypt_status_t *status)
-{
-   BSON_ASSERT_PARAM (findSpec);
-   BSON_ASSERT (findSpec->edgesInfo.set);
-
-   bson_type_t bsonType = bson_iter_type (&findSpec->edgesInfo.value.indexMin);
-
-   if (bson_iter_type (&findSpec->edgesInfo.value.indexMin) !=
-       bson_iter_type (&findSpec->edgesInfo.value.indexMax)) {
-      CLIENT_ERR (
-         "indexMin and indexMax must have the same type. Got: %s indexMin and "
-         "%s indexMax",
-         mc_bson_type_to_string (
-            bson_iter_type (&findSpec->edgesInfo.value.indexMin)),
-         mc_bson_type_to_string (
-            bson_iter_type (&findSpec->edgesInfo.value.indexMax)));
-      return NULL;
-   }
-
-   bson_iter_t lowerBound = findSpec->edgesInfo.value.lowerBound;
-   bson_iter_t upperBound = findSpec->edgesInfo.value.upperBound;
-   bool includeLowerBound = findSpec->edgesInfo.value.lbIncluded;
-   bool includeUpperBound = findSpec->edgesInfo.value.ubIncluded;
-
-   // Open-ended ranges are represented with infinity as the other endpoint.
-   // Resolve infinite bounds at this point to end at the min or max for this
-   // index.
-   if (isInfinite (&lowerBound)) {
-      lowerBound = findSpec->edgesInfo.value.indexMin;
-      includeLowerBound = true;
-   }
-   if (isInfinite (&upperBound)) {
-      upperBound = findSpec->edgesInfo.value.indexMax;
-      includeUpperBound = true;
-   }
-
-   if (bson_iter_type (&lowerBound) != bsonType) {
-      CLIENT_ERR ("expected lowerBound to match index type %s, got %s",
-                  mc_bson_type_to_string (bsonType),
-                  mc_bson_type_to_string (bson_iter_type (&lowerBound)));
-      return NULL;
-   }
-
-   if (bson_iter_type (&upperBound) != bsonType) {
-      CLIENT_ERR ("expected upperBound to match index type %s, got %s",
-                  mc_bson_type_to_string (bsonType),
-                  mc_bson_type_to_string (bson_iter_type (&upperBound)));
-      return NULL;
-   }
-
-   switch (bsonType) {
-   case BSON_TYPE_INT32:
-      BSON_ASSERT (bson_iter_type (&lowerBound) == BSON_TYPE_INT32);
-      BSON_ASSERT (bson_iter_type (&upperBound) == BSON_TYPE_INT32);
-      BSON_ASSERT (bson_iter_type (&findSpec->edgesInfo.value.indexMin) ==
-                   BSON_TYPE_INT32);
-      BSON_ASSERT (bson_iter_type (&findSpec->edgesInfo.value.indexMax) ==
-                   BSON_TYPE_INT32);
-      return mc_getMincoverInt32 (
-         (mc_getMincoverInt32_args_t){
-            .lowerBound = bson_iter_int32 (&lowerBound),
-            .includeLowerBound = includeLowerBound,
-            .upperBound = bson_iter_int32 (&upperBound),
-            .includeUpperBound = includeUpperBound,
-            .min =
-               OPT_I32 (bson_iter_int32 (&findSpec->edgesInfo.value.indexMin)),
-            .max =
-               OPT_I32 (bson_iter_int32 (&findSpec->edgesInfo.value.indexMax)),
-            .sparsity = sparsity},
-         status);
-
-   case BSON_TYPE_INT64:
-      BSON_ASSERT (bson_iter_type (&lowerBound) == BSON_TYPE_INT64);
-      BSON_ASSERT (bson_iter_type (&upperBound) == BSON_TYPE_INT64);
-      BSON_ASSERT (bson_iter_type (&findSpec->edgesInfo.value.indexMin) ==
-                   BSON_TYPE_INT64);
-      BSON_ASSERT (bson_iter_type (&findSpec->edgesInfo.value.indexMax) ==
-                   BSON_TYPE_INT64);
-      return mc_getMincoverInt64 (
-         (mc_getMincoverInt64_args_t){
-            .lowerBound = bson_iter_int64 (&lowerBound),
-            .includeLowerBound = includeLowerBound,
-            .upperBound = bson_iter_int64 (&upperBound),
-            .includeUpperBound = includeUpperBound,
-            .min =
-               OPT_I64 (bson_iter_int64 (&findSpec->edgesInfo.value.indexMin)),
-            .max =
-               OPT_I64 (bson_iter_int64 (&findSpec->edgesInfo.value.indexMax)),
-            .sparsity = sparsity},
-         status);
-   case BSON_TYPE_DATE_TIME:
-      BSON_ASSERT (bson_iter_type (&lowerBound) == BSON_TYPE_DATE_TIME);
-      BSON_ASSERT (bson_iter_type (&upperBound) == BSON_TYPE_DATE_TIME);
-      BSON_ASSERT (bson_iter_type (&findSpec->edgesInfo.value.indexMin) ==
-                   BSON_TYPE_DATE_TIME);
-      BSON_ASSERT (bson_iter_type (&findSpec->edgesInfo.value.indexMax) ==
-                   BSON_TYPE_DATE_TIME);
-      return mc_getMincoverInt64 (
-         (mc_getMincoverInt64_args_t){
-            .lowerBound = bson_iter_date_time (&lowerBound),
+mc_get_mincover_from_FLE2RangeFindSpec(mc_FLE2RangeFindSpec_t *findSpec, size_t sparsity, mongocrypt_status_t *status) {
+    BSON_ASSERT_PARAM(findSpec);
+    BSON_ASSERT(findSpec->edgesInfo.set);
+
+    bson_type_t bsonType = bson_iter_type(&findSpec->edgesInfo.value.indexMin);
+
+    if (bson_iter_type(&findSpec->edgesInfo.value.indexMin) != bson_iter_type(&findSpec->edgesInfo.value.indexMax)) {
+        CLIENT_ERR("indexMin and indexMax must have the same type. Got: %s indexMin and "
+                   "%s indexMax",
+                   mc_bson_type_to_string(bson_iter_type(&findSpec->edgesInfo.value.indexMin)),
+                   mc_bson_type_to_string(bson_iter_type(&findSpec->edgesInfo.value.indexMax)));
+        return NULL;
+    }
+
+    bson_iter_t lowerBound = findSpec->edgesInfo.value.lowerBound;
+    bson_iter_t upperBound = findSpec->edgesInfo.value.upperBound;
+    bool includeLowerBound = findSpec->edgesInfo.value.lbIncluded;
+    bool includeUpperBound = findSpec->edgesInfo.value.ubIncluded;
+
+    // Open-ended ranges are represented with infinity as the other endpoint.
+    // Resolve infinite bounds at this point to end at the min or max for this
+    // index.
+    if (isInfinite(&lowerBound)) {
+        lowerBound = findSpec->edgesInfo.value.indexMin;
+        includeLowerBound = true;
+    }
+    if (isInfinite(&upperBound)) {
+        upperBound = findSpec->edgesInfo.value.indexMax;
+        includeUpperBound = true;
+    }
+
+    if (bson_iter_type(&lowerBound) != bsonType) {
+        CLIENT_ERR("expected lowerBound to match index type %s, got %s",
+                   mc_bson_type_to_string(bsonType),
+                   mc_bson_type_to_string(bson_iter_type(&lowerBound)));
+        return NULL;
+    }
+
+    if (bson_iter_type(&upperBound) != bsonType) {
+        CLIENT_ERR("expected upperBound to match index type %s, got %s",
+                   mc_bson_type_to_string(bsonType),
+                   mc_bson_type_to_string(bson_iter_type(&upperBound)));
+        return NULL;
+    }
+
+    switch (bsonType) {
+    case BSON_TYPE_INT32:
+        BSON_ASSERT(bson_iter_type(&lowerBound) == BSON_TYPE_INT32);
+        BSON_ASSERT(bson_iter_type(&upperBound) == BSON_TYPE_INT32);
+        BSON_ASSERT(bson_iter_type(&findSpec->edgesInfo.value.indexMin) == BSON_TYPE_INT32);
+        BSON_ASSERT(bson_iter_type(&findSpec->edgesInfo.value.indexMax) == BSON_TYPE_INT32);
+        return mc_getMincoverInt32(
+            (mc_getMincoverInt32_args_t){.lowerBound = bson_iter_int32(&lowerBound),
+                                         .includeLowerBound = includeLowerBound,
+                                         .upperBound = bson_iter_int32(&upperBound),
+                                         .includeUpperBound = includeUpperBound,
+                                         .min = OPT_I32(bson_iter_int32(&findSpec->edgesInfo.value.indexMin)),
+                                         .max = OPT_I32(bson_iter_int32(&findSpec->edgesInfo.value.indexMax)),
+                                         .sparsity = sparsity},
+            status);
+
+    case BSON_TYPE_INT64:
+        BSON_ASSERT(bson_iter_type(&lowerBound) == BSON_TYPE_INT64);
+        BSON_ASSERT(bson_iter_type(&upperBound) == BSON_TYPE_INT64);
+        BSON_ASSERT(bson_iter_type(&findSpec->edgesInfo.value.indexMin) == BSON_TYPE_INT64);
+        BSON_ASSERT(bson_iter_type(&findSpec->edgesInfo.value.indexMax) == BSON_TYPE_INT64);
+        return mc_getMincoverInt64(
+            (mc_getMincoverInt64_args_t){.lowerBound = bson_iter_int64(&lowerBound),
+                                         .includeLowerBound = includeLowerBound,
+                                         .upperBound = bson_iter_int64(&upperBound),
+                                         .includeUpperBound = includeUpperBound,
+                                         .min = OPT_I64(bson_iter_int64(&findSpec->edgesInfo.value.indexMin)),
+                                         .max = OPT_I64(bson_iter_int64(&findSpec->edgesInfo.value.indexMax)),
+                                         .sparsity = sparsity},
+            status);
+    case BSON_TYPE_DATE_TIME:
+        BSON_ASSERT(bson_iter_type(&lowerBound) == BSON_TYPE_DATE_TIME);
+        BSON_ASSERT(bson_iter_type(&upperBound) == BSON_TYPE_DATE_TIME);
+        BSON_ASSERT(bson_iter_type(&findSpec->edgesInfo.value.indexMin) == BSON_TYPE_DATE_TIME);
+        BSON_ASSERT(bson_iter_type(&findSpec->edgesInfo.value.indexMax) == BSON_TYPE_DATE_TIME);
+        return mc_getMincoverInt64(
+            (mc_getMincoverInt64_args_t){.lowerBound = bson_iter_date_time(&lowerBound),
+                                         .includeLowerBound = includeLowerBound,
+                                         .upperBound = bson_iter_date_time(&upperBound),
+                                         .includeUpperBound = includeUpperBound,
+                                         .min = OPT_I64(bson_iter_date_time(&findSpec->edgesInfo.value.indexMin)),
+                                         .max = OPT_I64(bson_iter_date_time(&findSpec->edgesInfo.value.indexMax)),
+                                         .sparsity = sparsity},
+            status);
+    case BSON_TYPE_DOUBLE: {
+        BSON_ASSERT(bson_iter_type(&lowerBound) == BSON_TYPE_DOUBLE);
+        BSON_ASSERT(bson_iter_type(&upperBound) == BSON_TYPE_DOUBLE);
+        BSON_ASSERT(bson_iter_type(&findSpec->edgesInfo.value.indexMin) == BSON_TYPE_DOUBLE);
+        BSON_ASSERT(bson_iter_type(&findSpec->edgesInfo.value.indexMax) == BSON_TYPE_DOUBLE);
+
+        mc_getMincoverDouble_args_t args = {.lowerBound = bson_iter_double(&lowerBound),
+                                            .includeLowerBound = includeLowerBound,
+                                            .upperBound = bson_iter_double(&upperBound),
+                                            .includeUpperBound = includeUpperBound,
+                                            .sparsity = sparsity};
+        if (findSpec->edgesInfo.value.precision.set) {
+            // If precision is set, pass min/max/precision to mc_getMincoverDouble.
+            // Do not pass min/max if precision is not set. All three must be set
+            // or all three must be unset in mc_getTypeInfoDouble.
+            args.min = OPT_DOUBLE(bson_iter_double(&findSpec->edgesInfo.value.indexMin));
+            args.max = OPT_DOUBLE(bson_iter_double(&findSpec->edgesInfo.value.indexMax));
+            args.precision = findSpec->edgesInfo.value.precision;
+        }
+        return mc_getMincoverDouble(args, status);
+    }
+    case BSON_TYPE_DECIMAL128: {
+#if MONGOCRYPT_HAVE_DECIMAL128_SUPPORT
+        BSON_ASSERT(bson_iter_type(&lowerBound) == BSON_TYPE_DECIMAL128);
+        BSON_ASSERT(bson_iter_type(&upperBound) == BSON_TYPE_DECIMAL128);
+        BSON_ASSERT(bson_iter_type(&findSpec->edgesInfo.value.indexMin) == BSON_TYPE_DECIMAL128);
+        BSON_ASSERT(bson_iter_type(&findSpec->edgesInfo.value.indexMax) == BSON_TYPE_DECIMAL128);
+
+        mc_getMincoverDecimal128_args_t args = {
+            .lowerBound = mc_dec128_from_bson_iter(&lowerBound),
             .includeLowerBound = includeLowerBound,
-            .upperBound = bson_iter_date_time (&upperBound),
+            .upperBound = mc_dec128_from_bson_iter(&upperBound),
             .includeUpperBound = includeUpperBound,
-            .min = OPT_I64 (
-               bson_iter_date_time (&findSpec->edgesInfo.value.indexMin)),
-            .max = OPT_I64 (
-               bson_iter_date_time (&findSpec->edgesInfo.value.indexMax)),
-            .sparsity = sparsity},
-         status);
-   case BSON_TYPE_DOUBLE: {
-      BSON_ASSERT (bson_iter_type (&lowerBound) == BSON_TYPE_DOUBLE);
-      BSON_ASSERT (bson_iter_type (&upperBound) == BSON_TYPE_DOUBLE);
-      BSON_ASSERT (bson_iter_type (&findSpec->edgesInfo.value.indexMin) ==
-                   BSON_TYPE_DOUBLE);
-      BSON_ASSERT (bson_iter_type (&findSpec->edgesInfo.value.indexMax) ==
-                   BSON_TYPE_DOUBLE);
-
-      mc_getMincoverDouble_args_t args = {
-         .lowerBound = bson_iter_double (&lowerBound),
-         .includeLowerBound = includeLowerBound,
-         .upperBound = bson_iter_double (&upperBound),
-         .includeUpperBound = includeUpperBound,
-         .sparsity = sparsity};
-      if (findSpec->edgesInfo.value.precision.set) {
-         // If precision is set, pass min/max/precision to mc_getMincoverDouble.
-         // Do not pass min/max if precision is not set. All three must be set
-         // or all three must be unset in mc_getTypeInfoDouble.
-         args.min =
-            OPT_DOUBLE (bson_iter_double (&findSpec->edgesInfo.value.indexMin));
-         args.max =
-            OPT_DOUBLE (bson_iter_double (&findSpec->edgesInfo.value.indexMax));
-         args.precision = findSpec->edgesInfo.value.precision;
-      }
-      return mc_getMincoverDouble (args, status);
-   }
-   case BSON_TYPE_DECIMAL128: {
-#if MONGOCRYPT_HAVE_DECIMAL128_SUPPORT
-      BSON_ASSERT (bson_iter_type (&lowerBound) == BSON_TYPE_DECIMAL128);
-      BSON_ASSERT (bson_iter_type (&upperBound) == BSON_TYPE_DECIMAL128);
-      BSON_ASSERT (bson_iter_type (&findSpec->edgesInfo.value.indexMin) ==
-                   BSON_TYPE_DECIMAL128);
-      BSON_ASSERT (bson_iter_type (&findSpec->edgesInfo.value.indexMax) ==
-                   BSON_TYPE_DECIMAL128);
-
-      mc_getMincoverDecimal128_args_t args = {
-         .lowerBound = mc_dec128_from_bson_iter (&lowerBound),
-         .includeLowerBound = includeLowerBound,
-         .upperBound = mc_dec128_from_bson_iter (&upperBound),
-         .includeUpperBound = includeUpperBound,
-         .sparsity = sparsity,
-      };
-      if (findSpec->edgesInfo.value.precision.set) {
-         args.min = OPT_MC_DEC128 (
-            mc_dec128_from_bson_iter (&findSpec->edgesInfo.value.indexMin));
-         args.max = OPT_MC_DEC128 (
-            mc_dec128_from_bson_iter (&findSpec->edgesInfo.value.indexMax));
-         args.precision = findSpec->edgesInfo.value.precision;
-      }
-      return mc_getMincoverDecimal128 (args, status);
+            .sparsity = sparsity,
+        };
+        if (findSpec->edgesInfo.value.precision.set) {
+            args.min = OPT_MC_DEC128(mc_dec128_from_bson_iter(&findSpec->edgesInfo.value.indexMin));
+            args.max = OPT_MC_DEC128(mc_dec128_from_bson_iter(&findSpec->edgesInfo.value.indexMax));
+            args.precision = findSpec->edgesInfo.value.precision;
+        }
+        return mc_getMincoverDecimal128(args, status);
 #else // ↑↑↑↑↑↑↑↑ With Decimal128 / Without ↓↓↓↓↓↓↓↓↓↓
-      CLIENT_ERR ("FLE2 find is not supported for Decimal128: libmongocrypt "
-                  "was built without Decimal128 support");
-      return NULL;
+        CLIENT_ERR("FLE2 find is not supported for Decimal128: libmongocrypt "
+                   "was built without Decimal128 support");
+        return NULL;
 #endif
-   }
-
-   case BSON_TYPE_EOD:
-   case BSON_TYPE_UTF8:
-   case BSON_TYPE_DOCUMENT:
-   case BSON_TYPE_ARRAY:
-   case BSON_TYPE_BINARY:
-   case BSON_TYPE_UNDEFINED:
-   case BSON_TYPE_OID:
-   case BSON_TYPE_BOOL:
-   case BSON_TYPE_NULL:
-   case BSON_TYPE_REGEX:
-   case BSON_TYPE_DBPOINTER:
-   case BSON_TYPE_CODE:
-   case BSON_TYPE_SYMBOL:
-   case BSON_TYPE_CODEWSCOPE:
-   case BSON_TYPE_TIMESTAMP:
-   case BSON_TYPE_MAXKEY:
-   case BSON_TYPE_MINKEY:
-   default:
-      CLIENT_ERR ("FLE2 find is not supported for type: %s",
-                  mc_bson_type_to_string (bsonType));
-      return NULL;
-   }
+    }
+
+    case BSON_TYPE_EOD:
+    case BSON_TYPE_UTF8:
+    case BSON_TYPE_DOCUMENT:
+    case BSON_TYPE_ARRAY:
+    case BSON_TYPE_BINARY:
+    case BSON_TYPE_UNDEFINED:
+    case BSON_TYPE_OID:
+    case BSON_TYPE_BOOL:
+    case BSON_TYPE_NULL:
+    case BSON_TYPE_REGEX:
+    case BSON_TYPE_DBPOINTER:
+    case BSON_TYPE_CODE:
+    case BSON_TYPE_SYMBOL:
+    case BSON_TYPE_CODEWSCOPE:
+    case BSON_TYPE_TIMESTAMP:
+    case BSON_TYPE_MAXKEY:
+    case BSON_TYPE_MINKEY:
+    default: CLIENT_ERR("FLE2 find is not supported for type: %s", mc_bson_type_to_string(bsonType)); return NULL;
+    }
 }
 
-static bool
-_mongocrypt_fle2_placeholder_to_find_ciphertextForRange (
-   _mongocrypt_key_broker_t *kb,
-   _mongocrypt_marking_t *marking,
-   _mongocrypt_ciphertext_t *ciphertext,
-   mongocrypt_status_t *status)
-{
-   BSON_ASSERT_PARAM (kb);
-   BSON_ASSERT_PARAM (marking);
-   BSON_ASSERT_PARAM (ciphertext);
-   BSON_ASSERT (kb->crypt);
-
-   _mongocrypt_crypto_t *crypto = kb->crypt->crypto;
-   mc_FLE2EncryptionPlaceholder_t *placeholder = &marking->fle2;
-   mc_FLE2FindRangePayload_t payload;
-   bool res = false;
-   mc_mincover_t *mincover = NULL;
-   _mongocrypt_buffer_t tokenKey = {0};
-
-   BSON_ASSERT (marking->type == MONGOCRYPT_MARKING_FLE2_ENCRYPTION);
-   BSON_ASSERT (placeholder);
-   BSON_ASSERT (placeholder->type == MONGOCRYPT_FLE2_PLACEHOLDER_TYPE_FIND);
-   BSON_ASSERT (placeholder->algorithm == MONGOCRYPT_FLE2_ALGORITHM_RANGE);
-   _mongocrypt_ciphertext_init (ciphertext);
-   mc_FLE2FindRangePayload_init (&payload);
-
-   // Parse the query bounds and index bounds from FLE2EncryptionPlaceholder for
-   // range find.
-   mc_FLE2RangeFindSpec_t findSpec;
-   if (!mc_FLE2RangeFindSpec_parse (&findSpec, &placeholder->v_iter, status)) {
-      goto fail;
-   }
-
-   if (findSpec.edgesInfo.set) {
-      // cm := Queryable Encryption max counter
-      payload.payload.value.maxContentionCounter =
-         placeholder->maxContentionCounter;
-
-      // e := ServerDataEncryptionLevel1Token
-      {
-         if (!_get_tokenKey (
-                kb, &placeholder->index_key_id, &tokenKey, status)) {
-            goto fail;
-         }
-
-         mc_ServerDataEncryptionLevel1Token_t *serverToken =
-            mc_ServerDataEncryptionLevel1Token_new (crypto, &tokenKey, status);
-         if (!serverToken) {
-            goto fail;
-         }
-         _mongocrypt_buffer_copy_to (
-            mc_ServerDataEncryptionLevel1Token_get (serverToken),
-            &payload.payload.value.serverEncryptionToken);
-         mc_ServerDataEncryptionLevel1Token_destroy (serverToken);
-      }
-
-      // g:= array<EdgeFindTokenSet>
-      {
-         BSON_ASSERT (placeholder->sparsity >= 0 &&
-                      (uint64_t) placeholder->sparsity <= (uint64_t) SIZE_MAX);
-         mincover = mc_get_mincover_from_FLE2RangeFindSpec (
-            &findSpec, (size_t) placeholder->sparsity, status);
-         if (!mincover) {
-            goto fail;
-         }
-
-         for (size_t i = 0; i < mc_mincover_len (mincover); i++) {
-            // Create a EdgeFindTokenSet from each edge.
-            bool loop_ok = false;
-            const char *edge = mc_mincover_get (mincover, i);
-            _mongocrypt_buffer_t edge_buf = {0};
-            _FLE2EncryptedPayloadCommon_t edge_tokens = {{0}};
-            mc_EdgeFindTokenSet_t eftc = {{0}};
+/**
+ * Payload subtype 10: FLE2FindRangePayload
+ *
+ * {e: serverToken, cm: contentionCounter,
+ *  g: [{d: EDC, s: ESC, c: ECC}, ...]}
+ */
+static bool _mongocrypt_fle2_placeholder_to_find_ciphertextForRange_v1(_mongocrypt_key_broker_t *kb,
+                                                                       _mongocrypt_marking_t *marking,
+                                                                       _mongocrypt_ciphertext_t *ciphertext,
+                                                                       mongocrypt_status_t *status) {
+    BSON_ASSERT_PARAM(kb);
+    BSON_ASSERT_PARAM(marking);
+    BSON_ASSERT_PARAM(ciphertext);
+    BSON_ASSERT(kb->crypt);
+
+    _mongocrypt_crypto_t *crypto = kb->crypt->crypto;
+    mc_FLE2EncryptionPlaceholder_t *placeholder = &marking->fle2;
+    mc_FLE2FindRangePayload_t payload;
+    bool res = false;
+    mc_mincover_t *mincover = NULL;
+    _mongocrypt_buffer_t tokenKey = {0};
+
+    BSON_ASSERT(kb->crypt->opts.use_fle2_v2 == false);
+    BSON_ASSERT(marking->type == MONGOCRYPT_MARKING_FLE2_ENCRYPTION);
+    BSON_ASSERT(placeholder);
+    BSON_ASSERT(placeholder->type == MONGOCRYPT_FLE2_PLACEHOLDER_TYPE_FIND);
+    BSON_ASSERT(placeholder->algorithm == MONGOCRYPT_FLE2_ALGORITHM_RANGE);
+    mc_FLE2FindRangePayload_init(&payload);
+
+    // Parse the query bounds and index bounds from FLE2EncryptionPlaceholder for
+    // range find.
+    mc_FLE2RangeFindSpec_t findSpec;
+    if (!mc_FLE2RangeFindSpec_parse(&findSpec, &placeholder->v_iter, status)) {
+        goto fail;
+    }
+
+    if (findSpec.edgesInfo.set) {
+        // cm := Queryable Encryption max counter
+        payload.payload.value.maxContentionCounter = placeholder->maxContentionCounter;
+
+        // e := ServerDataEncryptionLevel1Token
+        {
+            if (!_get_tokenKey(kb, &placeholder->index_key_id, &tokenKey, status)) {
+                goto fail;
+            }
 
-            if (!_mongocrypt_buffer_from_string (&edge_buf, edge)) {
-               CLIENT_ERR ("failed to copy edge to buffer");
-               goto fail_loop;
+            mc_ServerDataEncryptionLevel1Token_t *serverToken =
+                mc_ServerDataEncryptionLevel1Token_new(crypto, &tokenKey, status);
+            if (!serverToken) {
+                goto fail;
+            }
+            _mongocrypt_buffer_copy_to(mc_ServerDataEncryptionLevel1Token_get(serverToken),
+                                       &payload.payload.value.serverEncryptionToken);
+            mc_ServerDataEncryptionLevel1Token_destroy(serverToken);
+        }
+
+        // g:= array<EdgeFindTokenSet>
+        {
+            BSON_ASSERT(placeholder->sparsity >= 0 && (uint64_t)placeholder->sparsity <= (uint64_t)SIZE_MAX);
+            mincover = mc_get_mincover_from_FLE2RangeFindSpec(&findSpec, (size_t)placeholder->sparsity, status);
+            if (!mincover) {
+                goto fail;
             }
 
-            if (!_mongocrypt_fle2_placeholder_common (
-                   kb,
-                   &edge_tokens,
-                   &placeholder->index_key_id,
-                   &edge_buf,
-                   false, /* derive tokens using counter */
-                   placeholder->maxContentionCounter,
-                   status)) {
-               goto fail_loop;
+            for (size_t i = 0; i < mc_mincover_len(mincover); i++) {
+                // Create a EdgeFindTokenSet from each edge.
+                bool loop_ok = false;
+                const char *edge = mc_mincover_get(mincover, i);
+                _mongocrypt_buffer_t edge_buf = {0};
+                _FLE2EncryptedPayloadCommon_t edge_tokens = {{0}};
+                mc_EdgeFindTokenSet_t eftc = {{0}};
+
+                if (!_mongocrypt_buffer_from_string(&edge_buf, edge)) {
+                    CLIENT_ERR("failed to copy edge to buffer");
+                    goto fail_loop;
+                }
+
+                if (!_mongocrypt_fle2_placeholder_common(kb,
+                                                         &edge_tokens,
+                                                         &placeholder->index_key_id,
+                                                         &edge_buf,
+                                                         false, /* derive tokens using counter */
+                                                         placeholder->maxContentionCounter,
+                                                         status)) {
+                    goto fail_loop;
+                }
+
+                // d := EDCDerivedToken
+                _mongocrypt_buffer_steal(&eftc.edcDerivedToken, &edge_tokens.edcDerivedToken);
+                // s := ESCDerivedToken
+                _mongocrypt_buffer_steal(&eftc.escDerivedToken, &edge_tokens.escDerivedToken);
+                // c := ECCDerivedToken
+                _mongocrypt_buffer_steal(&eftc.eccDerivedToken, &edge_tokens.eccDerivedToken);
+
+                _mc_array_append_val(&payload.payload.value.edgeFindTokenSetArray, eftc);
+
+                loop_ok = true;
+            fail_loop:
+                _FLE2EncryptedPayloadCommon_cleanup(&edge_tokens);
+                _mongocrypt_buffer_cleanup(&edge_buf);
+                if (!loop_ok) {
+                    goto fail;
+                }
             }
+        }
+        payload.payload.set = true;
+    }
+
+    payload.payloadId = findSpec.payloadId;
+    payload.firstOperator = findSpec.firstOperator;
+    payload.secondOperator = findSpec.secondOperator;
+
+    // Serialize.
+    {
+        bson_t out = BSON_INITIALIZER;
+        mc_FLE2FindRangePayload_serialize(&payload, &out);
+        _mongocrypt_buffer_steal_from_bson(&ciphertext->data, &out);
+    }
+    _mongocrypt_buffer_steal(&ciphertext->key_id, &placeholder->index_key_id);
+
+    // Do not set ciphertext->original_bson_type and ciphertext->key_id. They are
+    // not used for FLE2FindRangePayload.
+    ciphertext->blob_subtype = MC_SUBTYPE_FLE2FindRangePayload;
+
+    res = true;
+fail:
+    mc_mincover_destroy(mincover);
+    mc_FLE2FindRangePayload_cleanup(&payload);
+    _mongocrypt_buffer_cleanup(&tokenKey);
 
-            // d := EDCDerivedToken
-            _mongocrypt_buffer_steal (&eftc.edcDerivedToken,
-                                      &edge_tokens.edcDerivedToken);
-            // s := ESCDerivedToken
-            _mongocrypt_buffer_steal (&eftc.escDerivedToken,
-                                      &edge_tokens.escDerivedToken);
-            // c := ECCDerivedToken
-            _mongocrypt_buffer_steal (&eftc.eccDerivedToken,
-                                      &edge_tokens.eccDerivedToken);
+    return res;
+}
 
-            _mc_array_append_val (&payload.payload.value.edgeFindTokenSetArray,
-                                  eftc);
+/**
+ * Payload subtype 13: FLE2FindRangePayloadV2
+ * Delegates to ..._find_ciphertextForRange_v1
+ *   when crypt->opts.use_fle2_v2 is false
+ *
+ * {cm: contentionCounter,
+ *  g: [{d: EDC, s: ESC, l: serverDerivedFromDataToken}, ...]}
+ */
+static bool _mongocrypt_fle2_placeholder_to_find_ciphertextForRange(_mongocrypt_key_broker_t *kb,
+                                                                    _mongocrypt_marking_t *marking,
+                                                                    _mongocrypt_ciphertext_t *ciphertext,
+                                                                    mongocrypt_status_t *status) {
+    BSON_ASSERT_PARAM(kb);
+    BSON_ASSERT_PARAM(marking);
+    BSON_ASSERT_PARAM(ciphertext);
+
+    if (kb->crypt->opts.use_fle2_v2 == false) {
+        return _mongocrypt_fle2_placeholder_to_find_ciphertextForRange_v1(kb, marking, ciphertext, status);
+    }
+
+    mc_FLE2EncryptionPlaceholder_t *placeholder = &marking->fle2;
+    mc_FLE2FindRangePayloadV2_t payload;
+    bool res = false;
+    mc_mincover_t *mincover = NULL;
+    _mongocrypt_buffer_t tokenKey = {0};
+
+    BSON_ASSERT(marking->type == MONGOCRYPT_MARKING_FLE2_ENCRYPTION);
+    BSON_ASSERT(placeholder);
+    BSON_ASSERT(placeholder->type == MONGOCRYPT_FLE2_PLACEHOLDER_TYPE_FIND);
+    BSON_ASSERT(placeholder->algorithm == MONGOCRYPT_FLE2_ALGORITHM_RANGE);
+    mc_FLE2FindRangePayloadV2_init(&payload);
+
+    // Parse the query bounds and index bounds from FLE2EncryptionPlaceholder for
+    // range find.
+    mc_FLE2RangeFindSpec_t findSpec;
+    if (!mc_FLE2RangeFindSpec_parse(&findSpec, &placeholder->v_iter, status)) {
+        goto fail;
+    }
+
+    if (findSpec.edgesInfo.set) {
+        // cm := Queryable Encryption max counter
+        payload.payload.value.maxContentionCounter = placeholder->maxContentionCounter;
+
+        // g:= array<EdgeFindTokenSet>
+        {
+            BSON_ASSERT(placeholder->sparsity >= 0 && (uint64_t)placeholder->sparsity <= (uint64_t)SIZE_MAX);
+            mincover = mc_get_mincover_from_FLE2RangeFindSpec(&findSpec, (size_t)placeholder->sparsity, status);
+            if (!mincover) {
+                goto fail;
+            }
 
-            loop_ok = true;
-         fail_loop:
-            _FLE2EncryptedPayloadCommon_cleanup (&edge_tokens);
-            _mongocrypt_buffer_cleanup (&edge_buf);
-            if (!loop_ok) {
-               goto fail;
+            for (size_t i = 0; i < mc_mincover_len(mincover); i++) {
+                // Create a EdgeFindTokenSet from each edge.
+                bool loop_ok = false;
+                const char *edge = mc_mincover_get(mincover, i);
+                _mongocrypt_buffer_t edge_buf = {0};
+                _FLE2EncryptedPayloadCommon_t edge_tokens = {{0}};
+                mc_EdgeFindTokenSetV2_t eftc = {{0}};
+
+                if (!_mongocrypt_buffer_from_string(&edge_buf, edge)) {
+                    CLIENT_ERR("failed to copy edge to buffer");
+                    goto fail_loop;
+                }
+
+                if (!_mongocrypt_fle2_placeholder_common(kb,
+                                                         &edge_tokens,
+                                                         &placeholder->index_key_id,
+                                                         &edge_buf,
+                                                         false, /* derive tokens using counter */
+                                                         placeholder->maxContentionCounter,
+                                                         status)) {
+                    goto fail_loop;
+                }
+
+                // d := EDCDerivedToken
+                _mongocrypt_buffer_steal(&eftc.edcDerivedToken, &edge_tokens.edcDerivedToken);
+                // s := ESCDerivedToken
+                _mongocrypt_buffer_steal(&eftc.escDerivedToken, &edge_tokens.escDerivedToken);
+
+                // l := serverDerivedFromDataToken
+                _mongocrypt_buffer_steal(&eftc.serverDerivedFromDataToken, &edge_tokens.serverDerivedFromDataToken);
+
+                _mc_array_append_val(&payload.payload.value.edgeFindTokenSetArray, eftc);
+
+                loop_ok = true;
+            fail_loop:
+                _FLE2EncryptedPayloadCommon_cleanup(&edge_tokens);
+                _mongocrypt_buffer_cleanup(&edge_buf);
+                if (!loop_ok) {
+                    goto fail;
+                }
             }
-         }
-      }
-      payload.payload.set = true;
-   }
-
-   payload.payloadId = findSpec.payloadId;
-   payload.firstOperator = findSpec.firstOperator;
-   payload.secondOperator = findSpec.secondOperator;
-
-   // Serialize.
-   {
-      bson_t out = BSON_INITIALIZER;
-      mc_FLE2FindRangePayload_serialize (&payload, &out);
-      _mongocrypt_buffer_steal_from_bson (&ciphertext->data, &out);
-   }
-   _mongocrypt_buffer_steal (&ciphertext->key_id, &placeholder->index_key_id);
-
-   // Do not set ciphertext->original_bson_type and ciphertext->key_id. They are
-   // not used for FLE2FindRangePayload.
-   ciphertext->blob_subtype = MC_SUBTYPE_FLE2FindRangePayload;
-
-   res = true;
+        }
+        payload.payload.set = true;
+    }
+
+    payload.payloadId = findSpec.payloadId;
+    payload.firstOperator = findSpec.firstOperator;
+    payload.secondOperator = findSpec.secondOperator;
+
+    // Serialize.
+    {
+        bson_t out = BSON_INITIALIZER;
+        mc_FLE2FindRangePayloadV2_serialize(&payload, &out);
+        _mongocrypt_buffer_steal_from_bson(&ciphertext->data, &out);
+    }
+    _mongocrypt_buffer_steal(&ciphertext->key_id, &placeholder->index_key_id);
+
+    // Do not set ciphertext->original_bson_type and ciphertext->key_id. They are
+    // not used for FLE2FindRangePayloadV2.
+    ciphertext->blob_subtype = MC_SUBTYPE_FLE2FindRangePayloadV2;
+
+    res = true;
 fail:
-   mc_mincover_destroy (mincover);
-   mc_FLE2FindRangePayload_cleanup (&payload);
-   _mongocrypt_buffer_cleanup (&tokenKey);
+    mc_mincover_destroy(mincover);
+    mc_FLE2FindRangePayloadV2_cleanup(&payload);
+    _mongocrypt_buffer_cleanup(&tokenKey);
 
-   return res;
+    return res;
 }
 
-static bool
-_mongocrypt_fle2_placeholder_to_FLE2UnindexedEncryptedValue (
-   _mongocrypt_key_broker_t *kb,
-   _mongocrypt_marking_t *marking,
-   _mongocrypt_ciphertext_t *ciphertext,
-   mongocrypt_status_t *status)
-{
-   BSON_ASSERT_PARAM (kb);
-   BSON_ASSERT_PARAM (marking);
-   BSON_ASSERT_PARAM (ciphertext);
-
-   _mongocrypt_buffer_t plaintext = {0};
-   mc_FLE2EncryptionPlaceholder_t *placeholder = &marking->fle2;
-   _mongocrypt_buffer_t user_key = {0};
-   bool res = false;
-
-   BSON_ASSERT (marking->type == MONGOCRYPT_MARKING_FLE2_ENCRYPTION);
-   BSON_ASSERT (placeholder);
-   BSON_ASSERT (placeholder->algorithm == MONGOCRYPT_FLE2_ALGORITHM_UNINDEXED);
-   _mongocrypt_ciphertext_init (ciphertext);
-   _mongocrypt_buffer_from_iter (&plaintext, &placeholder->v_iter);
-
-   if (!_mongocrypt_key_broker_decrypted_key_by_id (
-          kb, &placeholder->user_key_id, &user_key)) {
-      CLIENT_ERR ("unable to retrieve key");
-      goto fail;
-   }
-
-   BSON_ASSERT (kb->crypt);
-   if (!mc_FLE2UnindexedEncryptedValue_encrypt (
-          kb->crypt->crypto,
-          &placeholder->user_key_id,
-          bson_iter_type (&placeholder->v_iter),
-          &plaintext,
-          &user_key,
-          &ciphertext->data,
-          status)) {
-      goto fail;
-   }
-
-   _mongocrypt_buffer_steal (&ciphertext->key_id, &placeholder->user_key_id);
-   ciphertext->original_bson_type =
-      (uint8_t) bson_iter_type (&placeholder->v_iter);
-   ciphertext->blob_subtype = MC_SUBTYPE_FLE2UnindexedEncryptedValue;
-   res = true;
+static bool _mongocrypt_fle2_placeholder_to_FLE2UnindexedEncryptedValue(_mongocrypt_key_broker_t *kb,
+                                                                        _mongocrypt_marking_t *marking,
+                                                                        _mongocrypt_ciphertext_t *ciphertext,
+                                                                        mongocrypt_status_t *status) {
+    BSON_ASSERT_PARAM(kb);
+    BSON_ASSERT_PARAM(marking);
+    BSON_ASSERT_PARAM(ciphertext);
+
+    _mongocrypt_buffer_t plaintext = {0};
+    mc_FLE2EncryptionPlaceholder_t *placeholder = &marking->fle2;
+    _mongocrypt_buffer_t user_key = {0};
+    bool res = false;
+
+    BSON_ASSERT(marking->type == MONGOCRYPT_MARKING_FLE2_ENCRYPTION);
+    BSON_ASSERT(placeholder);
+    BSON_ASSERT(placeholder->algorithm == MONGOCRYPT_FLE2_ALGORITHM_UNINDEXED);
+    _mongocrypt_buffer_from_iter(&plaintext, &placeholder->v_iter);
+
+    if (!_mongocrypt_key_broker_decrypted_key_by_id(kb, &placeholder->user_key_id, &user_key)) {
+        CLIENT_ERR("unable to retrieve key");
+        goto fail;
+    }
+
+    BSON_ASSERT(kb->crypt);
+    if (kb->crypt->opts.use_fle2_v2) {
+        res = mc_FLE2UnindexedEncryptedValueV2_encrypt(kb->crypt->crypto,
+                                                       &placeholder->user_key_id,
+                                                       bson_iter_type(&placeholder->v_iter),
+                                                       &plaintext,
+                                                       &user_key,
+                                                       &ciphertext->data,
+                                                       status);
+        ciphertext->blob_subtype = MC_SUBTYPE_FLE2UnindexedEncryptedValueV2;
+    } else {
+        res = mc_FLE2UnindexedEncryptedValue_encrypt(kb->crypt->crypto,
+                                                     &placeholder->user_key_id,
+                                                     bson_iter_type(&placeholder->v_iter),
+                                                     &plaintext,
+                                                     &user_key,
+                                                     &ciphertext->data,
+                                                     status);
+        ciphertext->blob_subtype = MC_SUBTYPE_FLE2UnindexedEncryptedValue;
+    }
+
+    if (!res) {
+        goto fail;
+    }
+
+    _mongocrypt_buffer_steal(&ciphertext->key_id, &placeholder->user_key_id);
+    ciphertext->original_bson_type = (uint8_t)bson_iter_type(&placeholder->v_iter);
+
+    res = true;
 fail:
-   _mongocrypt_buffer_cleanup (&plaintext);
-   _mongocrypt_buffer_cleanup (&user_key);
+    _mongocrypt_buffer_cleanup(&plaintext);
+    _mongocrypt_buffer_cleanup(&user_key);
 
-   return res;
+    return res;
 }
 
-static bool
-_mongocrypt_fle1_marking_to_ciphertext (_mongocrypt_key_broker_t *kb,
-                                        _mongocrypt_marking_t *marking,
-                                        _mongocrypt_ciphertext_t *ciphertext,
-                                        mongocrypt_status_t *status)
-{
-   _mongocrypt_buffer_t plaintext;
-   _mongocrypt_buffer_t iv;
-   _mongocrypt_buffer_t associated_data;
-   _mongocrypt_buffer_t key_material;
-   _mongocrypt_buffer_t key_id;
-   bool ret = false;
-   bool key_found;
-   uint32_t bytes_written;
-
-   BSON_ASSERT_PARAM (kb);
-   BSON_ASSERT_PARAM (marking);
-   BSON_ASSERT_PARAM (ciphertext);
-
-   BSON_ASSERT ((marking->type == MONGOCRYPT_MARKING_FLE1_BY_ID) ||
-                (marking->type == MONGOCRYPT_MARKING_FLE1_BY_ALTNAME));
-
-   _mongocrypt_buffer_init (&plaintext);
-   _mongocrypt_buffer_init (&associated_data);
-   _mongocrypt_buffer_init (&iv);
-   _mongocrypt_buffer_init (&key_id);
-   _mongocrypt_buffer_init (&key_material);
-
-   /* Get the decrypted key for this marking. */
-   if (marking->type == MONGOCRYPT_MARKING_FLE1_BY_ALTNAME) {
-      key_found = _mongocrypt_key_broker_decrypted_key_by_name (
-         kb, &marking->key_alt_name, &key_material, &key_id);
-   } else if (!_mongocrypt_buffer_empty (&marking->key_id)) {
-      key_found = _mongocrypt_key_broker_decrypted_key_by_id (
-         kb, &marking->key_id, &key_material);
-      _mongocrypt_buffer_copy_to (&marking->key_id, &key_id);
-   } else {
-      CLIENT_ERR ("marking must have either key_id or key_alt_name");
-      goto fail;
-   }
-
-   if (!key_found) {
-      _mongocrypt_status_copy_to (kb->status, status);
-      goto fail;
-   }
-
-   _mongocrypt_ciphertext_init (ciphertext);
-   ciphertext->original_bson_type = (uint8_t) bson_iter_type (&marking->v_iter);
-   if (marking->algorithm == MONGOCRYPT_ENCRYPTION_ALGORITHM_DETERMINISTIC) {
-      ciphertext->blob_subtype = MC_SUBTYPE_FLE1DeterministicEncryptedValue;
-   } else {
-      BSON_ASSERT (marking->algorithm ==
-                   MONGOCRYPT_ENCRYPTION_ALGORITHM_RANDOM);
-      ciphertext->blob_subtype = MC_SUBTYPE_FLE1RandomEncryptedValue;
-   }
-   _mongocrypt_buffer_copy_to (&key_id, &ciphertext->key_id);
-   if (!_mongocrypt_ciphertext_serialize_associated_data (ciphertext,
-                                                          &associated_data)) {
-      CLIENT_ERR ("could not serialize associated data");
-      goto fail;
-   }
-
-   _mongocrypt_buffer_from_iter (&plaintext, &marking->v_iter);
-   ciphertext->data.len =
-      _mongocrypt_calculate_ciphertext_len (plaintext.len, status);
-   if (ciphertext->data.len == 0) {
-      goto fail;
-   }
-   ciphertext->data.data = bson_malloc (ciphertext->data.len);
-   BSON_ASSERT (ciphertext->data.data);
-
-   ciphertext->data.owned = true;
-
-   BSON_ASSERT (kb->crypt);
-   switch (marking->algorithm) {
-   case MONGOCRYPT_ENCRYPTION_ALGORITHM_DETERMINISTIC:
-      /* Use deterministic encryption. */
-      _mongocrypt_buffer_resize (&iv, MONGOCRYPT_IV_LEN);
-      ret = _mongocrypt_calculate_deterministic_iv (kb->crypt->crypto,
-                                                    &key_material,
-                                                    &plaintext,
-                                                    &associated_data,
-                                                    &iv,
-                                                    status);
-      if (!ret) {
-         goto fail;
-      }
-
-      ret = _mongocrypt_do_encryption (kb->crypt->crypto,
-                                       &iv,
-                                       &associated_data,
-                                       &key_material,
-                                       &plaintext,
-                                       &ciphertext->data,
-                                       &bytes_written,
-                                       status);
-      break;
-   case MONGOCRYPT_ENCRYPTION_ALGORITHM_RANDOM:
-      /* Use randomized encryption.
-       * In this case, we must generate a new, random iv. */
-      _mongocrypt_buffer_resize (&iv, MONGOCRYPT_IV_LEN);
-      if (!_mongocrypt_random (
-             kb->crypt->crypto, &iv, MONGOCRYPT_IV_LEN, status)) {
-         goto fail;
-      }
-      ret = _mongocrypt_do_encryption (kb->crypt->crypto,
-                                       &iv,
-                                       &associated_data,
-                                       &key_material,
-                                       &plaintext,
-                                       &ciphertext->data,
-                                       &bytes_written,
-                                       status);
-      break;
-   case MONGOCRYPT_ENCRYPTION_ALGORITHM_NONE:
-   default:
-      /* Error. */
-      CLIENT_ERR ("Unsupported value for encryption algorithm");
-      goto fail;
-   }
-
-   if (!ret) {
-      goto fail;
-   }
-
-   BSON_ASSERT (bytes_written == ciphertext->data.len);
-
-   ret = true;
+static bool _mongocrypt_fle1_marking_to_ciphertext(_mongocrypt_key_broker_t *kb,
+                                                   _mongocrypt_marking_t *marking,
+                                                   _mongocrypt_ciphertext_t *ciphertext,
+                                                   mongocrypt_status_t *status) {
+    const _mongocrypt_value_encryption_algorithm_t *fle1 = _mcFLE1Algorithm();
+    _mongocrypt_buffer_t plaintext;
+    _mongocrypt_buffer_t iv;
+    _mongocrypt_buffer_t associated_data;
+    _mongocrypt_buffer_t key_material;
+    _mongocrypt_buffer_t key_id;
+    bool ret = false;
+    bool key_found;
+    uint32_t bytes_written;
+
+    BSON_ASSERT_PARAM(kb);
+    BSON_ASSERT_PARAM(marking);
+    BSON_ASSERT_PARAM(ciphertext);
+
+    BSON_ASSERT((marking->type == MONGOCRYPT_MARKING_FLE1_BY_ID)
+                || (marking->type == MONGOCRYPT_MARKING_FLE1_BY_ALTNAME));
+
+    _mongocrypt_buffer_init(&plaintext);
+    _mongocrypt_buffer_init(&associated_data);
+    _mongocrypt_buffer_init(&iv);
+    _mongocrypt_buffer_init(&key_id);
+    _mongocrypt_buffer_init(&key_material);
+
+    /* Get the decrypted key for this marking. */
+    if (marking->type == MONGOCRYPT_MARKING_FLE1_BY_ALTNAME) {
+        key_found = _mongocrypt_key_broker_decrypted_key_by_name(kb, &marking->key_alt_name, &key_material, &key_id);
+    } else if (!_mongocrypt_buffer_empty(&marking->key_id)) {
+        key_found = _mongocrypt_key_broker_decrypted_key_by_id(kb, &marking->key_id, &key_material);
+        _mongocrypt_buffer_copy_to(&marking->key_id, &key_id);
+    } else {
+        CLIENT_ERR("marking must have either key_id or key_alt_name");
+        goto fail;
+    }
+
+    if (!key_found) {
+        _mongocrypt_status_copy_to(kb->status, status);
+        goto fail;
+    }
+
+    ciphertext->original_bson_type = (uint8_t)bson_iter_type(&marking->v_iter);
+    if (marking->algorithm == MONGOCRYPT_ENCRYPTION_ALGORITHM_DETERMINISTIC) {
+        ciphertext->blob_subtype = MC_SUBTYPE_FLE1DeterministicEncryptedValue;
+    } else {
+        BSON_ASSERT(marking->algorithm == MONGOCRYPT_ENCRYPTION_ALGORITHM_RANDOM);
+        ciphertext->blob_subtype = MC_SUBTYPE_FLE1RandomEncryptedValue;
+    }
+    _mongocrypt_buffer_copy_to(&key_id, &ciphertext->key_id);
+    if (!_mongocrypt_ciphertext_serialize_associated_data(ciphertext, &associated_data)) {
+        CLIENT_ERR("could not serialize associated data");
+        goto fail;
+    }
+
+    _mongocrypt_buffer_from_iter(&plaintext, &marking->v_iter);
+    ciphertext->data.len = fle1->get_ciphertext_len(plaintext.len, status);
+    if (ciphertext->data.len == 0) {
+        goto fail;
+    }
+    ciphertext->data.data = bson_malloc(ciphertext->data.len);
+    BSON_ASSERT(ciphertext->data.data);
+
+    ciphertext->data.owned = true;
+
+    BSON_ASSERT(kb->crypt);
+    switch (marking->algorithm) {
+    case MONGOCRYPT_ENCRYPTION_ALGORITHM_DETERMINISTIC:
+        /* Use deterministic encryption. */
+        _mongocrypt_buffer_resize(&iv, MONGOCRYPT_IV_LEN);
+        ret = _mongocrypt_calculate_deterministic_iv(kb->crypt->crypto,
+                                                     &key_material,
+                                                     &plaintext,
+                                                     &associated_data,
+                                                     &iv,
+                                                     status);
+        if (!ret) {
+            goto fail;
+        }
+
+        ret = fle1->do_encrypt(kb->crypt->crypto,
+                               &iv,
+                               &associated_data,
+                               &key_material,
+                               &plaintext,
+                               &ciphertext->data,
+                               &bytes_written,
+                               status);
+        break;
+    case MONGOCRYPT_ENCRYPTION_ALGORITHM_RANDOM:
+        /* Use randomized encryption.
+         * In this case, we must generate a new, random iv. */
+        _mongocrypt_buffer_resize(&iv, MONGOCRYPT_IV_LEN);
+        if (!_mongocrypt_random(kb->crypt->crypto, &iv, MONGOCRYPT_IV_LEN, status)) {
+            goto fail;
+        }
+        ret = fle1->do_encrypt(kb->crypt->crypto,
+                               &iv,
+                               &associated_data,
+                               &key_material,
+                               &plaintext,
+                               &ciphertext->data,
+                               &bytes_written,
+                               status);
+        break;
+    case MONGOCRYPT_ENCRYPTION_ALGORITHM_NONE:
+    default:
+        /* Error. */
+        CLIENT_ERR("Unsupported value for encryption algorithm");
+        goto fail;
+    }
+
+    if (!ret) {
+        goto fail;
+    }
+
+    BSON_ASSERT(bytes_written == ciphertext->data.len);
+
+    ret = true;
 
 fail:
-   _mongocrypt_buffer_cleanup (&iv);
-   _mongocrypt_buffer_cleanup (&key_id);
-   _mongocrypt_buffer_cleanup (&plaintext);
-   _mongocrypt_buffer_cleanup (&associated_data);
-   _mongocrypt_buffer_cleanup (&key_material);
-   return ret;
+    _mongocrypt_buffer_cleanup(&iv);
+    _mongocrypt_buffer_cleanup(&key_id);
+    _mongocrypt_buffer_cleanup(&plaintext);
+    _mongocrypt_buffer_cleanup(&associated_data);
+    _mongocrypt_buffer_cleanup(&key_material);
+    return ret;
 }
 
-bool
-_mongocrypt_marking_to_ciphertext (void *ctx,
-                                   _mongocrypt_marking_t *marking,
-                                   _mongocrypt_ciphertext_t *ciphertext,
-                                   mongocrypt_status_t *status)
-{
-   BSON_ASSERT_PARAM (marking);
-   BSON_ASSERT_PARAM (ciphertext);
-   BSON_ASSERT_PARAM (ctx);
-
-   _mongocrypt_key_broker_t *kb = (_mongocrypt_key_broker_t *) ctx;
-
-   switch (marking->type) {
-   case MONGOCRYPT_MARKING_FLE2_ENCRYPTION:
-      switch (marking->fle2.algorithm) {
-      case MONGOCRYPT_FLE2_ALGORITHM_UNINDEXED:
-         return _mongocrypt_fle2_placeholder_to_FLE2UnindexedEncryptedValue (
-            kb, marking, ciphertext, status);
-      case MONGOCRYPT_FLE2_ALGORITHM_RANGE:
-         switch (marking->fle2.type) {
-         case MONGOCRYPT_FLE2_PLACEHOLDER_TYPE_INSERT:
-            return _mongocrypt_fle2_placeholder_to_insert_update_ciphertextForRange (
-               kb, marking, ciphertext, status);
-         case MONGOCRYPT_FLE2_PLACEHOLDER_TYPE_FIND:
-            return _mongocrypt_fle2_placeholder_to_find_ciphertextForRange (
-               kb, marking, ciphertext, status);
-         default:
-            CLIENT_ERR ("unexpected fle2 type: %d", (int) marking->fle2.type);
-            return false;
-         }
-      case MONGOCRYPT_FLE2_ALGORITHM_EQUALITY:
-         switch (marking->fle2.type) {
-         case MONGOCRYPT_FLE2_PLACEHOLDER_TYPE_INSERT:
-            return _mongocrypt_fle2_placeholder_to_insert_update_ciphertext (
-               kb, marking, ciphertext, status);
-         case MONGOCRYPT_FLE2_PLACEHOLDER_TYPE_FIND:
-            return _mongocrypt_fle2_placeholder_to_find_ciphertext (
-               kb, marking, ciphertext, status);
-         default:
-            CLIENT_ERR ("unexpected fle2 type: %d", (int) marking->fle2.type);
-            return false;
-         }
-      default:
-         CLIENT_ERR ("unexpected algorithm: %d", (int) marking->algorithm);
-         return false;
-      }
-   case MONGOCRYPT_MARKING_FLE1_BY_ID:
-   case MONGOCRYPT_MARKING_FLE1_BY_ALTNAME:
-      return _mongocrypt_fle1_marking_to_ciphertext (
-         kb, marking, ciphertext, status);
-   default:
-      CLIENT_ERR ("unexpected marking type: %d", (int) marking->type);
-      return false;
-   }
+bool _mongocrypt_marking_to_ciphertext(void *ctx,
+                                       _mongocrypt_marking_t *marking,
+                                       _mongocrypt_ciphertext_t *ciphertext,
+                                       mongocrypt_status_t *status) {
+    BSON_ASSERT_PARAM(marking);
+    BSON_ASSERT_PARAM(ciphertext);
+    BSON_ASSERT_PARAM(ctx);
+
+    _mongocrypt_key_broker_t *kb = (_mongocrypt_key_broker_t *)ctx;
+
+    switch (marking->type) {
+    case MONGOCRYPT_MARKING_FLE2_ENCRYPTION:
+        switch (marking->fle2.algorithm) {
+        case MONGOCRYPT_FLE2_ALGORITHM_UNINDEXED:
+            return _mongocrypt_fle2_placeholder_to_FLE2UnindexedEncryptedValue(kb, marking, ciphertext, status);
+        case MONGOCRYPT_FLE2_ALGORITHM_RANGE:
+            switch (marking->fle2.type) {
+            case MONGOCRYPT_FLE2_PLACEHOLDER_TYPE_INSERT:
+                return _mongocrypt_fle2_placeholder_to_insert_update_ciphertextForRange(kb,
+                                                                                        marking,
+                                                                                        ciphertext,
+                                                                                        status);
+            case MONGOCRYPT_FLE2_PLACEHOLDER_TYPE_FIND:
+                return _mongocrypt_fle2_placeholder_to_find_ciphertextForRange(kb, marking, ciphertext, status);
+            default: CLIENT_ERR("unexpected fle2 type: %d", (int)marking->fle2.type); return false;
+            }
+        case MONGOCRYPT_FLE2_ALGORITHM_EQUALITY:
+            switch (marking->fle2.type) {
+            case MONGOCRYPT_FLE2_PLACEHOLDER_TYPE_INSERT:
+                return _mongocrypt_fle2_placeholder_to_insert_update_ciphertext(kb, marking, ciphertext, status);
+            case MONGOCRYPT_FLE2_PLACEHOLDER_TYPE_FIND:
+                return _mongocrypt_fle2_placeholder_to_find_ciphertext(kb, marking, ciphertext, status);
+            default: CLIENT_ERR("unexpected fle2 type: %d", (int)marking->fle2.type); return false;
+            }
+        default: CLIENT_ERR("unexpected algorithm: %d", (int)marking->algorithm); return false;
+        }
+    case MONGOCRYPT_MARKING_FLE1_BY_ID:
+    case MONGOCRYPT_MARKING_FLE1_BY_ALTNAME:
+        return _mongocrypt_fle1_marking_to_ciphertext(kb, marking, ciphertext, status);
+    default: CLIENT_ERR("unexpected marking type: %d", (int)marking->type); return false;
+    }
 }