libmongocrypt-helper 1.7.0.0.1001 → 1.7.4.0.1000

data/ext/libmongocrypt/libmongocrypt/src/mongocrypt-ctx-encrypt.c

@@ -0,0 +1,3005 @@
+/*
+ * Copyright 2019-present MongoDB, Inc.
+ *
+ * Licensed under the Apache License, Version 2.0 (the "License");
+ * you may not use this file except in compliance with the License.
+ * You may obtain a copy of the License at
+ *
+ *   http://www.apache.org/licenses/LICENSE-2.0
+ *
+ * Unless required by applicable law or agreed to in writing, software
+ * distributed under the License is distributed on an "AS IS" BASIS,
+ * WITHOUT WARRANTIES OR CONDITIONS OF ANY KIND, either express or implied.
+ * See the License for the specific language governing permissions and
+ * limitations under the License.
+ */
+
+#include "mongocrypt-ciphertext-private.h"
+#include "mongocrypt-crypto-private.h"
+#include "mongocrypt-ctx-private.h"
+#include "mongocrypt-key-broker-private.h"
+#include "mongocrypt-marking-private.h"
+#include "mongocrypt-traverse-util-private.h"
+#include "mc-fle2-rfds-private.h"
+#include "mc-tokens-private.h"
+#include "mongocrypt-util-private.h" // mc_iter_document_as_bson
+
+/* _fle2_append_encryptedFieldConfig copies encryptedFieldConfig and applies
+ * default state collection names for escCollection, eccCollection, and
+ * ecocCollection if required. */
+static bool
+_fle2_append_encryptedFieldConfig (bson_t *dst,
+                                   bson_t *encryptedFieldConfig,
+                                   const char *coll_name,
+                                   mongocrypt_status_t *status)
+{
+   bson_iter_t iter;
+   bool has_escCollection = false;
+   bool has_eccCollection = false;
+   bool has_ecocCollection = false;
+
+   BSON_ASSERT_PARAM (dst);
+   BSON_ASSERT_PARAM (encryptedFieldConfig);
+   BSON_ASSERT_PARAM (coll_name);
+
+   if (!bson_iter_init (&iter, encryptedFieldConfig)) {
+      CLIENT_ERR ("unable to iterate encryptedFieldConfig");
+      return false;
+   }
+
+   while (bson_iter_next (&iter)) {
+      if (strcmp (bson_iter_key (&iter), "escCollection") == 0) {
+         has_escCollection = true;
+      }
+      if (strcmp (bson_iter_key (&iter), "eccCollection") == 0) {
+         has_eccCollection = true;
+      }
+      if (strcmp (bson_iter_key (&iter), "ecocCollection") == 0) {
+         has_ecocCollection = true;
+      }
+      if (!BSON_APPEND_VALUE (
+             dst, bson_iter_key (&iter), bson_iter_value (&iter))) {
+         CLIENT_ERR ("unable to append field: %s", bson_iter_key (&iter));
+         return false;
+      }
+   }
+
+   if (!has_escCollection) {
+      char *default_escCollection =
+         bson_strdup_printf ("enxcol_.%s.esc", coll_name);
+      if (!BSON_APPEND_UTF8 (dst, "escCollection", default_escCollection)) {
+         CLIENT_ERR ("unable to append escCollection");
+         bson_free (default_escCollection);
+         return false;
+      }
+      bson_free (default_escCollection);
+   }
+   if (!has_eccCollection) {
+      char *default_eccCollection =
+         bson_strdup_printf ("enxcol_.%s.ecc", coll_name);
+      if (!BSON_APPEND_UTF8 (dst, "eccCollection", default_eccCollection)) {
+         CLIENT_ERR ("unable to append eccCollection");
+         bson_free (default_eccCollection);
+         return false;
+      }
+      bson_free (default_eccCollection);
+   }
+   if (!has_ecocCollection) {
+      char *default_ecocCollection =
+         bson_strdup_printf ("enxcol_.%s.ecoc", coll_name);
+      if (!BSON_APPEND_UTF8 (dst, "ecocCollection", default_ecocCollection)) {
+         CLIENT_ERR ("unable to append ecocCollection");
+         bson_free (default_ecocCollection);
+         return false;
+      }
+      bson_free (default_ecocCollection);
+   }
+   return true;
+}
+
+static bool
+_fle2_append_encryptionInformation (bson_t *dst,
+                                    const char *ns,
+                                    bson_t *encryptedFieldConfig,
+                                    bson_t *deleteTokens,
+                                    const char *coll_name,
+                                    mongocrypt_status_t *status)
+{
+   bson_t encryption_information_bson;
+   bson_t schema_bson;
+   bson_t encrypted_field_config_bson;
+
+   BSON_ASSERT_PARAM (dst);
+   BSON_ASSERT_PARAM (ns);
+   BSON_ASSERT_PARAM (encryptedFieldConfig);
+   /* deleteTokens may be NULL */
+   BSON_ASSERT_PARAM (coll_name);
+
+   if (!BSON_APPEND_DOCUMENT_BEGIN (
+          dst, "encryptionInformation", &encryption_information_bson)) {
+      CLIENT_ERR ("unable to begin appending 'encryptionInformation'");
+      return false;
+   }
+   if (!BSON_APPEND_INT32 (&encryption_information_bson, "type", 1)) {
+      CLIENT_ERR ("unable to append type to 'encryptionInformation'");
+      return false;
+   }
+   if (!BSON_APPEND_DOCUMENT_BEGIN (
+          &encryption_information_bson, "schema", &schema_bson)) {
+      CLIENT_ERR (
+         "unable to begin appending 'schema' to 'encryptionInformation'");
+      return false;
+   }
+
+   if (!BSON_APPEND_DOCUMENT_BEGIN (
+          &schema_bson, ns, &encrypted_field_config_bson)) {
+      CLIENT_ERR ("unable to begin appending 'encryptedFieldConfig' to "
+                  "'encryptionInformation'.'schema'");
+      return false;
+   }
+
+   if (!_fle2_append_encryptedFieldConfig (&encrypted_field_config_bson,
+                                           encryptedFieldConfig,
+                                           coll_name,
+                                           status)) {
+      return false;
+   }
+
+   if (!bson_append_document_end (&schema_bson, &encrypted_field_config_bson)) {
+      CLIENT_ERR ("unable to end appending 'encryptedFieldConfig' to "
+                  "'encryptionInformation'.'schema'");
+      return false;
+   }
+   if (!bson_append_document_end (&encryption_information_bson, &schema_bson)) {
+      CLIENT_ERR (
+         "unable to end appending 'schema' to 'encryptionInformation'");
+      return false;
+   }
+
+   if (deleteTokens != NULL) {
+      bson_t delete_tokens_bson;
+      if (!BSON_APPEND_DOCUMENT_BEGIN (&encryption_information_bson,
+                                       "deleteTokens",
+                                       &delete_tokens_bson)) {
+         CLIENT_ERR ("unable to begin appending 'deleteTokens' to "
+                     "'encryptionInformation'");
+         return false;
+      }
+      if (!BSON_APPEND_DOCUMENT (&delete_tokens_bson, ns, deleteTokens)) {
+         CLIENT_ERR ("unable to append '%s' to 'deleteTokens'", ns);
+         return false;
+      }
+      if (!bson_append_document_end (&encryption_information_bson,
+                                     &delete_tokens_bson)) {
+         CLIENT_ERR ("unable to end appending 'deleteTokens' to "
+                     "'encryptionInformation'");
+         return false;
+      }
+   }
+
+   if (!bson_append_document_end (dst, &encryption_information_bson)) {
+      CLIENT_ERR ("unable to end appending 'encryptionInformation'");
+      return false;
+   }
+   return true;
+}
+
+typedef enum { MC_TO_CSFLE, MC_TO_MONGOCRYPTD, MC_TO_MONGOD } mc_cmd_target_t;
+
+/**
+ * @brief Add "encryptionInformation" to a command.
+ *
+ * @param cmd_name The name of the command.
+ * @param cmd The command being rewritten. It is an input and output.
+ * @param ns The <db>.<collection> namespace for the command.
+ * @param encryptedFieldConfig The "encryptedFields" document for the
+ * collection.
+ * @param deleteTokens Delete tokens to append to "encryptionInformation". May
+ * be NULL.
+ * @param coll_name The collection name.
+ * @param cmd_target The intended destination of the command. csfle,
+ * mongocryptd, and mongod have different requirements for the location of
+ * "encryptionInformation".
+ * @param status Output status.
+ * @return true On success
+ * @return false Otherwise. Sets a failing status message in this case.
+ */
+static bool
+_fle2_insert_encryptionInformation (const char *cmd_name,
+                                    bson_t *cmd /* in and out */,
+                                    const char *ns,
+                                    bson_t *encryptedFieldConfig,
+                                    bson_t *deleteTokens,
+                                    const char *coll_name,
+                                    mc_cmd_target_t cmd_target,
+                                    mongocrypt_status_t *status)
+{
+   bson_t out = BSON_INITIALIZER;
+   bson_t explain = BSON_INITIALIZER;
+   bson_iter_t iter;
+   bool ok = false;
+
+   BSON_ASSERT_PARAM (cmd_name);
+   BSON_ASSERT_PARAM (cmd);
+   BSON_ASSERT_PARAM (ns);
+   BSON_ASSERT_PARAM (encryptedFieldConfig);
+   /* deleteTokens may be NULL */
+   BSON_ASSERT_PARAM (coll_name);
+
+   if (0 != strcmp (cmd_name, "explain") || cmd_target == MC_TO_MONGOCRYPTD) {
+      // All commands except "explain" expect "encryptionInformation"
+      // at top-level. "explain" sent to mongocryptd expects
+      // "encryptionInformation" at top-level.
+      if (!_fle2_append_encryptionInformation (
+             cmd, ns, encryptedFieldConfig, deleteTokens, coll_name, status)) {
+         goto fail;
+      }
+      goto success;
+   }
+
+   // The "explain" command for csfle is a special case.
+   // mongocryptd expects "encryptionInformation" to be a sibling of the
+   // "explain" document. Example:
+   // {
+   //    "explain": { "find": "to-mongocryptd" },
+   //    "encryptionInformation": {}
+   // }
+   // csfle and mongod expect "encryptionInformation" to be nested in the
+   // "explain" document. Example:
+   // {
+   //    "explain": {
+   //       "find": "to-csfle-or-mongod"
+   //       "encryptionInformation": {}
+   //    }
+   // }
+   BSON_ASSERT (bson_iter_init_find (&iter, cmd, "explain"));
+   if (!BSON_ITER_HOLDS_DOCUMENT (&iter)) {
+      CLIENT_ERR ("expected 'explain' to be document");
+      goto fail;
+   }
+
+   {
+      bson_t tmp;
+      if (!mc_iter_document_as_bson (&iter, &tmp, status)) {
+         goto fail;
+      }
+      bson_copy_to (&tmp, &explain);
+   }
+
+   if (!_fle2_append_encryptionInformation (&explain,
+                                            ns,
+                                            encryptedFieldConfig,
+                                            deleteTokens,
+                                            coll_name,
+                                            status)) {
+      goto fail;
+   }
+
+   if (!BSON_APPEND_DOCUMENT (&out, "explain", &explain)) {
+      CLIENT_ERR ("unable to append 'explain' document");
+      goto fail;
+   }
+
+   bson_copy_to_excluding_noinit (cmd, &out, "explain", NULL);
+   bson_destroy (cmd);
+   if (!bson_steal (cmd, &out)) {
+      CLIENT_ERR ("failed to steal BSON without encryptionInformation");
+      goto fail;
+   }
+
+success:
+   ok = true;
+fail:
+   bson_destroy (&explain);
+   if (!ok) {
+      bson_destroy (&out);
+   }
+   return ok;
+}
+
+/* Construct the list collections command to send. */
+static bool
+_mongo_op_collinfo (mongocrypt_ctx_t *ctx, mongocrypt_binary_t *out)
+{
+   _mongocrypt_ctx_encrypt_t *ectx;
+   bson_t *cmd;
+
+   BSON_ASSERT_PARAM (ctx);
+   BSON_ASSERT_PARAM (out);
+
+   ectx = (_mongocrypt_ctx_encrypt_t *) ctx;
+   cmd = BCON_NEW ("name", BCON_UTF8 (ectx->coll_name));
+   CRYPT_TRACEF (&ectx->parent.crypt->log, "constructed: %s\n", tmp_json (cmd));
+   _mongocrypt_buffer_steal_from_bson (&ectx->list_collections_filter, cmd);
+   out->data = ectx->list_collections_filter.data;
+   out->len = ectx->list_collections_filter.len;
+   return true;
+}
+
+static bool
+_set_schema_from_collinfo (mongocrypt_ctx_t *ctx, bson_t *collinfo)
+{
+   bson_iter_t iter;
+   _mongocrypt_ctx_encrypt_t *ectx;
+   bool found_jsonschema = false;
+
+   BSON_ASSERT_PARAM (ctx);
+   BSON_ASSERT_PARAM (collinfo);
+
+   /* Parse out the schema. */
+   ectx = (_mongocrypt_ctx_encrypt_t *) ctx;
+
+   /* Disallow views. */
+   if (bson_iter_init_find (&iter, collinfo, "type") &&
+       BSON_ITER_HOLDS_UTF8 (&iter) && bson_iter_utf8 (&iter, NULL) &&
+       0 == strcmp ("view", bson_iter_utf8 (&iter, NULL))) {
+      return _mongocrypt_ctx_fail_w_msg (ctx, "cannot auto encrypt a view");
+   }
+
+   if (!bson_iter_init (&iter, collinfo)) {
+      return _mongocrypt_ctx_fail_w_msg (ctx, "BSON malformed");
+   }
+
+   if (bson_iter_find_descendant (&iter, "options.encryptedFields", &iter)) {
+      if (!BSON_ITER_HOLDS_DOCUMENT (&iter)) {
+         return _mongocrypt_ctx_fail_w_msg (
+            ctx, "options.encryptedFields is not a BSON document");
+      }
+      if (!_mongocrypt_buffer_copy_from_document_iter (
+             &ectx->encrypted_field_config, &iter)) {
+         return _mongocrypt_ctx_fail_w_msg (
+            ctx, "unable to copy options.encryptedFields");
+      }
+      bson_t efc_bson;
+      if (!_mongocrypt_buffer_to_bson (&ectx->encrypted_field_config,
+                                       &efc_bson)) {
+         return _mongocrypt_ctx_fail_w_msg (
+            ctx, "unable to create BSON from encrypted_field_config");
+      }
+      if (!mc_EncryptedFieldConfig_parse (&ectx->efc, &efc_bson, ctx->status)) {
+         _mongocrypt_ctx_fail (ctx);
+         return false;
+      }
+   }
+
+   BSON_ASSERT (bson_iter_init (&iter, collinfo));
+
+   if (bson_iter_find_descendant (&iter, "options.validator", &iter) &&
+       BSON_ITER_HOLDS_DOCUMENT (&iter)) {
+      if (!bson_iter_recurse (&iter, &iter)) {
+         return _mongocrypt_ctx_fail_w_msg (ctx, "BSON malformed");
+      }
+      while (bson_iter_next (&iter)) {
+         const char *key;
+
+         key = bson_iter_key (&iter);
+         BSON_ASSERT (key);
+         if (0 == strcmp ("$jsonSchema", key)) {
+            if (found_jsonschema) {
+               return _mongocrypt_ctx_fail_w_msg (
+                  ctx, "duplicate $jsonSchema fields found");
+            }
+            if (!_mongocrypt_buffer_copy_from_document_iter (&ectx->schema,
+                                                             &iter)) {
+               return _mongocrypt_ctx_fail_w_msg (ctx, "malformed $jsonSchema");
+            }
+            found_jsonschema = true;
+         } else {
+            ectx->collinfo_has_siblings = true;
+         }
+      }
+   }
+
+   if (!found_jsonschema) {
+      bson_t empty = BSON_INITIALIZER;
+
+      _mongocrypt_buffer_steal_from_bson (&ectx->schema, &empty);
+   }
+
+
+   return true;
+}
+
+/* get_command_name returns the name of a command. The command name is the first
+ * field. For example, the command name of: {"find": "foo", "filter": {"bar":
+ * 1}} is "find". */
+static const char *
+get_command_name (_mongocrypt_buffer_t *cmd, mongocrypt_status_t *status)
+{
+   bson_t cmd_bson;
+   bson_iter_t iter;
+   const char *cmd_name;
+
+   BSON_ASSERT_PARAM (cmd);
+
+   if (!_mongocrypt_buffer_to_bson (cmd, &cmd_bson)) {
+      CLIENT_ERR ("unable to convert command buffer to BSON");
+      return NULL;
+   }
+
+   if (!bson_iter_init (&iter, &cmd_bson)) {
+      CLIENT_ERR ("unable to iterate over command BSON");
+      return NULL;
+   }
+
+   /* The command name is the first key. */
+   if (!bson_iter_next (&iter)) {
+      CLIENT_ERR ("unexpected empty BSON for command");
+      return NULL;
+   }
+
+   cmd_name = bson_iter_key (&iter);
+   if (!cmd_name) {
+      CLIENT_ERR ("unable to get command name from BSON");
+      return NULL;
+   }
+   return cmd_name;
+}
+
+static bool
+command_needs_deleteTokens (const char *command_name)
+{
+   const char *cmds_needing_deleteTokens[] = {
+      "delete", "update", "findAndModify"};
+
+   BSON_ASSERT_PARAM (command_name);
+
+   size_t i;
+   for (i = 0; i < sizeof (cmds_needing_deleteTokens) /
+                      sizeof (cmds_needing_deleteTokens[0]);
+        i++) {
+      if (0 == strcmp (cmds_needing_deleteTokens[i], command_name)) {
+         return true;
+      }
+   }
+   return false;
+}
+
+/* context_uses_fle2 returns true if the context uses FLE 2 behavior.
+ * If a collection has an encryptedFields document, it uses FLE 2.
+ */
+static bool
+context_uses_fle2 (mongocrypt_ctx_t *ctx)
+{
+   _mongocrypt_ctx_encrypt_t *ectx = (_mongocrypt_ctx_encrypt_t *) ctx;
+
+   BSON_ASSERT_PARAM (ctx);
+
+   return !_mongocrypt_buffer_empty (&ectx->encrypted_field_config);
+}
+
+/* _fle2_collect_keys_for_deleteTokens requests keys required to produce
+ * deleteTokens. deleteTokens is only applicable to FLE 2. */
+static bool
+_fle2_collect_keys_for_deleteTokens (mongocrypt_ctx_t *ctx)
+{
+   _mongocrypt_ctx_encrypt_t *ectx = (_mongocrypt_ctx_encrypt_t *) ctx;
+
+   BSON_ASSERT_PARAM (ctx);
+
+   /* deleteTokens are only appended for FLE 2. */
+   if (!context_uses_fle2 (ctx)) {
+      return true;
+   }
+
+   const char *cmd_name = ectx->cmd_name;
+
+   if (!command_needs_deleteTokens (cmd_name)) {
+      /* Command does not require deleteTokens. */
+      return true;
+   }
+
+   mc_EncryptedField_t *field;
+
+   for (field = ectx->efc.fields; field != NULL; field = field->next) {
+      if (field->has_queries) {
+         if (!_mongocrypt_key_broker_request_id (&ctx->kb, &field->keyId)) {
+            _mongocrypt_key_broker_status (&ctx->kb, ctx->status);
+            _mongocrypt_ctx_fail (ctx);
+            return false;
+         }
+      }
+   }
+   return true;
+}
+
+/* _fle2_collect_keys_for_compact requests keys required to produce
+ * compactionTokens. compactionTokens is only applicable to FLE 2. */
+static bool
+_fle2_collect_keys_for_compact (mongocrypt_ctx_t *ctx)
+{
+   _mongocrypt_ctx_encrypt_t *ectx = (_mongocrypt_ctx_encrypt_t *) ctx;
+
+   BSON_ASSERT_PARAM (ctx);
+
+   /* compactionTokens are only appended for FLE 2. */
+   if (!context_uses_fle2 (ctx)) {
+      return true;
+   }
+
+   const char *cmd_name = ectx->cmd_name;
+
+   if (0 != strcmp (cmd_name, "compactStructuredEncryptionData")) {
+      return true;
+   }
+
+   /* compactStructuredEncryptionData must not be sent to mongocryptd. */
+   ectx->bypass_query_analysis = true;
+
+   mc_EncryptedField_t *field;
+
+   for (field = ectx->efc.fields; field != NULL; field = field->next) {
+      if (!_mongocrypt_key_broker_request_id (&ctx->kb, &field->keyId)) {
+         _mongocrypt_key_broker_status (&ctx->kb, ctx->status);
+         _mongocrypt_ctx_fail (ctx);
+         return false;
+      }
+   }
+   return true;
+}
+
+static bool
+_mongo_feed_collinfo (mongocrypt_ctx_t *ctx, mongocrypt_binary_t *in)
+{
+   bson_t as_bson;
+
+   _mongocrypt_ctx_encrypt_t *ectx;
+
+   BSON_ASSERT_PARAM (ctx);
+   BSON_ASSERT_PARAM (in);
+
+   ectx = (_mongocrypt_ctx_encrypt_t *) ctx;
+   if (!bson_init_static (&as_bson, in->data, in->len)) {
+      return _mongocrypt_ctx_fail_w_msg (ctx, "BSON malformed");
+   }
+
+   /* Cache the received collinfo. */
+   if (!_mongocrypt_cache_add_copy (
+          &ctx->crypt->cache_collinfo, ectx->ns, &as_bson, ctx->status)) {
+      return _mongocrypt_ctx_fail (ctx);
+   }
+
+   if (!_set_schema_from_collinfo (ctx, &as_bson)) {
+      return false;
+   }
+
+   return true;
+}
+
+static bool
+_try_run_csfle_marking (mongocrypt_ctx_t *ctx);
+
+static bool
+_mongo_done_collinfo (mongocrypt_ctx_t *ctx)
+{
+   _mongocrypt_ctx_encrypt_t *ectx;
+
+   BSON_ASSERT_PARAM (ctx);
+
+   ectx = (_mongocrypt_ctx_encrypt_t *) ctx;
+   if (_mongocrypt_buffer_empty (&ectx->schema)) {
+      bson_t empty_collinfo = BSON_INITIALIZER;
+
+      /* If no collinfo was fed, cache an empty collinfo. */
+      if (!_mongocrypt_cache_add_copy (&ctx->crypt->cache_collinfo,
+                                       ectx->ns,
+                                       &empty_collinfo,
+                                       ctx->status)) {
+         bson_destroy (&empty_collinfo);
+         return _mongocrypt_ctx_fail (ctx);
+      }
+      bson_destroy (&empty_collinfo);
+   }
+
+   if (!_fle2_collect_keys_for_deleteTokens (ctx)) {
+      return false;
+   }
+
+   if (!_fle2_collect_keys_for_compact (ctx)) {
+      return false;
+   }
+
+   if (ectx->bypass_query_analysis) {
+      /* Keys may have been requested for deleteTokens or compactionTokens.
+       * Finish key requests. */
+      _mongocrypt_key_broker_requests_done (&ctx->kb);
+      return _mongocrypt_ctx_state_from_key_broker (ctx);
+   }
+   ectx->parent.state = MONGOCRYPT_CTX_NEED_MONGO_MARKINGS;
+   return _try_run_csfle_marking (ctx);
+}
+
+
+static bool
+_fle2_mongo_op_markings (mongocrypt_ctx_t *ctx, bson_t *out)
+{
+   _mongocrypt_ctx_encrypt_t *ectx;
+   bson_t cmd_bson = BSON_INITIALIZER,
+          encrypted_field_config_bson = BSON_INITIALIZER;
+
+   BSON_ASSERT_PARAM (ctx);
+   BSON_ASSERT_PARAM (out);
+
+   ectx = (_mongocrypt_ctx_encrypt_t *) ctx;
+
+   BSON_ASSERT (ctx->state == MONGOCRYPT_CTX_NEED_MONGO_MARKINGS);
+   BSON_ASSERT (context_uses_fle2 (ctx));
+
+   if (!_mongocrypt_buffer_to_bson (&ectx->original_cmd, &cmd_bson)) {
+      return _mongocrypt_ctx_fail_w_msg (
+         ctx, "unable to convert original_cmd to BSON");
+   }
+
+   if (!_mongocrypt_buffer_to_bson (&ectx->encrypted_field_config,
+                                    &encrypted_field_config_bson)) {
+      return _mongocrypt_ctx_fail_w_msg (
+         ctx, "unable to convert encrypted_field_config to BSON");
+   }
+
+   const char *cmd_name = ectx->cmd_name;
+
+   // If input command included $db, do not include it in the command to
+   // mongocryptd. Drivers are expected to append $db in the RunCommand helper
+   // used to send the command.
+   bson_init (out);
+   bson_copy_to_excluding_noinit (&cmd_bson, out, "$db", NULL);
+   if (!_fle2_insert_encryptionInformation (
+          cmd_name,
+          out,
+          ectx->ns,
+          &encrypted_field_config_bson,
+          NULL /* deleteTokens */,
+          ectx->coll_name,
+          ctx->crypt->csfle.okay ? MC_TO_CSFLE : MC_TO_MONGOCRYPTD,
+          ctx->status)) {
+      return _mongocrypt_ctx_fail (ctx);
+   }
+   return true;
+}
+
+
+/**
+ * @brief Create the server-side command that contains information for
+ * generating encryption markings via query analysis.
+ *
+ * @param ctx The encryption context.
+ * @param out The destination of the generated BSON document
+ * @return true On success
+ * @return false Otherwise. Sets a failing status message in this case.
+ */
+static bool
+_create_markings_cmd_bson (mongocrypt_ctx_t *ctx, bson_t *out)
+{
+   _mongocrypt_ctx_encrypt_t *ectx = (_mongocrypt_ctx_encrypt_t *) ctx;
+
+   BSON_ASSERT_PARAM (ctx);
+   BSON_ASSERT_PARAM (out);
+
+   if (context_uses_fle2 (ctx)) {
+      // Defer to FLE2 to generate the markings command
+      return _fle2_mongo_op_markings (ctx, out);
+   }
+
+   // For FLE1:
+   // Get the original command document
+   bson_t bson_view = BSON_INITIALIZER;
+   if (!_mongocrypt_buffer_to_bson (&ectx->original_cmd, &bson_view)) {
+      _mongocrypt_ctx_fail_w_msg (ctx, "invalid BSON cmd");
+      return false;
+   }
+
+   // Copy the command to the output
+   // If input command included $db, do not include it in the command to
+   // mongocryptd. Drivers are expected to append $db in the RunCommand helper
+   // used to send the command.
+   bson_init (out);
+   bson_copy_to_excluding_noinit (&bson_view, out, "$db", NULL);
+
+   if (!_mongocrypt_buffer_empty (&ectx->schema)) {
+      // We have a schema buffer. View it as BSON:
+      if (!_mongocrypt_buffer_to_bson (&ectx->schema, &bson_view)) {
+         _mongocrypt_ctx_fail_w_msg (ctx, "invalid BSON schema");
+         return false;
+      }
+      // Append the jsonSchema to the output command
+      BSON_APPEND_DOCUMENT (out, "jsonSchema", &bson_view);
+   } else {
+      bson_t empty = BSON_INITIALIZER;
+      BSON_APPEND_DOCUMENT (out, "jsonSchema", &empty);
+   }
+
+   // if a local schema was not set, set isRemoteSchema=true
+   BSON_APPEND_BOOL (out, "isRemoteSchema", !ectx->used_local_schema);
+   return true;
+}
+
+
+static bool
+_mongo_op_markings (mongocrypt_ctx_t *ctx, mongocrypt_binary_t *out)
+{
+   _mongocrypt_ctx_encrypt_t *ectx = (_mongocrypt_ctx_encrypt_t *) ctx;
+
+   BSON_ASSERT_PARAM (ctx);
+   BSON_ASSERT_PARAM (out);
+
+   if (ectx->ismaster.needed) {
+      if (_mongocrypt_buffer_empty (&ectx->ismaster.cmd)) {
+         bson_t ismaster_cmd = BSON_INITIALIZER;
+         // Store the generated command:
+         BSON_APPEND_INT32 (&ismaster_cmd, "isMaster", 1);
+         _mongocrypt_buffer_steal_from_bson (&ectx->ismaster.cmd,
+                                             &ismaster_cmd);
+      }
+
+      out->data = ectx->ismaster.cmd.data;
+      out->len = ectx->ismaster.cmd.len;
+      return true;
+   }
+
+   if (_mongocrypt_buffer_empty (&ectx->mongocryptd_cmd)) {
+      // We need to generate the command document
+      bson_t cmd_bson = BSON_INITIALIZER;
+      if (!_create_markings_cmd_bson (ctx, &cmd_bson)) {
+         // Failed
+         bson_destroy (&cmd_bson);
+         return false;
+      }
+      // Store the generated command:
+      _mongocrypt_buffer_steal_from_bson (&ectx->mongocryptd_cmd, &cmd_bson);
+   }
+
+   // If we reach here, we have a valid mongocrypt_cmd
+   out->data = ectx->mongocryptd_cmd.data;
+   out->len = ectx->mongocryptd_cmd.len;
+   return true;
+}
+
+
+static bool
+_collect_key_from_marking (void *ctx,
+                           _mongocrypt_buffer_t *in,
+                           mongocrypt_status_t *status)
+{
+   _mongocrypt_marking_t marking;
+   _mongocrypt_key_broker_t *kb;
+   bool res;
+
+   BSON_ASSERT_PARAM (ctx);
+   BSON_ASSERT_PARAM (in);
+
+   kb = (_mongocrypt_key_broker_t *) ctx;
+
+   if (!_mongocrypt_marking_parse_unowned (in, &marking, status)) {
+      _mongocrypt_marking_cleanup (&marking);
+      return false;
+   }
+
+   if (marking.type == MONGOCRYPT_MARKING_FLE1_BY_ID) {
+      res = _mongocrypt_key_broker_request_id (kb, &marking.key_id);
+   } else if (marking.type == MONGOCRYPT_MARKING_FLE1_BY_ALTNAME) {
+      res = _mongocrypt_key_broker_request_name (kb, &marking.key_alt_name);
+   } else {
+      BSON_ASSERT (marking.type == MONGOCRYPT_MARKING_FLE2_ENCRYPTION);
+      res =
+         _mongocrypt_key_broker_request_id (kb, &marking.fle2.index_key_id) &&
+         _mongocrypt_key_broker_request_id (kb, &marking.fle2.user_key_id);
+   }
+
+   if (!res) {
+      _mongocrypt_key_broker_status (kb, status);
+      _mongocrypt_marking_cleanup (&marking);
+      return false;
+   }
+
+   _mongocrypt_marking_cleanup (&marking);
+
+   return true;
+}
+
+
+static bool
+_mongo_feed_markings (mongocrypt_ctx_t *ctx, mongocrypt_binary_t *in)
+{
+   /* Find keys. */
+   bson_t as_bson;
+   bson_iter_t iter;
+   _mongocrypt_ctx_encrypt_t *ectx;
+
+   BSON_ASSERT_PARAM (ctx);
+   BSON_ASSERT_PARAM (in);
+
+   ectx = (_mongocrypt_ctx_encrypt_t *) ctx;
+   if (!_mongocrypt_binary_to_bson (in, &as_bson)) {
+      return _mongocrypt_ctx_fail_w_msg (ctx, "malformed BSON");
+   }
+
+   if (ectx->ismaster.needed) {
+      /* This is a response to the 'isMaster' command. */
+      if (!bson_iter_init_find (&iter, &as_bson, "maxWireVersion")) {
+         return _mongocrypt_ctx_fail_w_msg (
+            ctx,
+            "expected to find 'maxWireVersion' in isMaster response, but did "
+            "not.");
+      }
+      if (!BSON_ITER_HOLDS_INT32 (&iter)) {
+         return _mongocrypt_ctx_fail_w_msg (
+            ctx, "expected 'maxWireVersion' to be int32.");
+      }
+      ectx->ismaster.maxwireversion = bson_iter_int32 (&iter);
+      return true;
+   }
+
+   if (bson_iter_init_find (&iter, &as_bson, "schemaRequiresEncryption") &&
+       !bson_iter_as_bool (&iter)) {
+      /* TODO: update cache: this schema does not require encryption. */
+
+      /* If using a local schema, warn if there are no encrypted fields. */
+      if (ectx->used_local_schema) {
+         _mongocrypt_log (
+            &ctx->crypt->log,
+            MONGOCRYPT_LOG_LEVEL_WARNING,
+            "local schema used but does not have encryption specifiers");
+      }
+      return true;
+   } else {
+      /* if the schema requires encryption, but has sibling validators, error.
+       */
+      if (ectx->collinfo_has_siblings) {
+         return _mongocrypt_ctx_fail_w_msg (ctx,
+                                            "schema requires encryption, "
+                                            "but collection JSON schema "
+                                            "validator has siblings");
+      }
+   }
+
+   if (bson_iter_init_find (&iter, &as_bson, "hasEncryptedPlaceholders") &&
+       !bson_iter_as_bool (&iter)) {
+      return true;
+   }
+
+   if (!bson_iter_init_find (&iter, &as_bson, "result")) {
+      return _mongocrypt_ctx_fail_w_msg (ctx, "malformed marking, no 'result'");
+   }
+
+   if (!_mongocrypt_buffer_copy_from_document_iter (&ectx->marked_cmd, &iter)) {
+      return _mongocrypt_ctx_fail_w_msg (
+         ctx, "malformed marking, 'result' must be a document");
+   }
+
+   if (!bson_iter_recurse (&iter, &iter)) {
+      return _mongocrypt_ctx_fail_w_msg (
+         ctx, "malformed marking, could not recurse into 'result'");
+   }
+   if (!_mongocrypt_traverse_binary_in_bson (_collect_key_from_marking,
+                                             (void *) &ctx->kb,
+                                             TRAVERSE_MATCH_MARKING,
+                                             &iter,
+                                             ctx->status)) {
+      return _mongocrypt_ctx_fail (ctx);
+   }
+
+   return true;
+}
+
+static bool
+mongocrypt_ctx_encrypt_ismaster_done (mongocrypt_ctx_t *ctx);
+
+static bool
+_mongo_done_markings (mongocrypt_ctx_t *ctx)
+{
+   _mongocrypt_ctx_encrypt_t *ectx = (_mongocrypt_ctx_encrypt_t *) ctx;
+
+   BSON_ASSERT_PARAM (ctx);
+
+   if (ectx->ismaster.needed) {
+      return mongocrypt_ctx_encrypt_ismaster_done (ctx);
+   }
+   (void) _mongocrypt_key_broker_requests_done (&ctx->kb);
+   return _mongocrypt_ctx_state_from_key_broker (ctx);
+}
+
+/**
+ * @brief Append $db to a command being passed to csfle.
+ */
+static bool
+_add_dollar_db (const char *cmd_name,
+                bson_t *cmd,
+                const char *db_name,
+                mongocrypt_status_t *status)
+{
+   bson_t out = BSON_INITIALIZER;
+   bson_t explain = BSON_INITIALIZER;
+   bson_iter_t iter;
+   bool ok = false;
+
+   BSON_ASSERT_PARAM (cmd_name);
+   BSON_ASSERT_PARAM (cmd);
+   BSON_ASSERT_PARAM (db_name);
+
+   if (!bson_iter_init_find (&iter, cmd, "$db")) {
+      if (!BSON_APPEND_UTF8 (cmd, "$db", db_name)) {
+         CLIENT_ERR ("failed to append '$db'");
+         goto fail;
+      }
+   }
+
+   if (0 != strcmp (cmd_name, "explain")) {
+      goto success;
+   }
+
+   // The "explain" command for csfle is a special case.
+   // csfle expects "$db" to be nested in the "explain" document and match the
+   // top-level "$db". Example:
+   // {
+   //    "explain": {
+   //       "find": "to-csfle"
+   //       "$db": "db"
+   //    }
+   //    "$db": "db"
+   // }
+   BSON_ASSERT (bson_iter_init_find (&iter, cmd, "explain"));
+   if (!BSON_ITER_HOLDS_DOCUMENT (&iter)) {
+      CLIENT_ERR ("expected 'explain' to be document");
+      goto fail;
+   }
+
+   {
+      bson_t tmp;
+      if (!mc_iter_document_as_bson (&iter, &tmp, status)) {
+         goto fail;
+      }
+      bson_copy_to (&tmp, &explain);
+   }
+
+   if (!BSON_APPEND_UTF8 (&explain, "$db", db_name)) {
+      CLIENT_ERR ("failed to append '$db'");
+      goto fail;
+   }
+
+   if (!BSON_APPEND_DOCUMENT (&out, "explain", &explain)) {
+      CLIENT_ERR ("unable to append 'explain' document");
+      goto fail;
+   }
+
+   bson_copy_to_excluding_noinit (cmd, &out, "explain", NULL);
+   bson_destroy (cmd);
+   if (!bson_steal (cmd, &out)) {
+      CLIENT_ERR ("failed to steal BSON without encryptionInformation");
+      goto fail;
+   }
+
+success:
+   ok = true;
+fail:
+   bson_destroy (&explain);
+   if (!ok) {
+      bson_destroy (&out);
+   }
+   return ok;
+}
+
+/**
+ * @brief Attempt to generate csfle markings using a csfle dynamic library.
+ *
+ * @param ctx A context which has state NEED_MONGO_MARKINGS
+ * @return true On success
+ * @return false On error.
+ *
+ * This should be called only when we are ready for markings in the command
+ * document. This function will only do anything if the csfle dynamic library
+ * is loaded, otherwise it returns success immediately and leaves the state
+ * as NEED_MONGO_MARKINGS.
+ *
+ * If csfle is loaded, this function will request the csfle library generate a
+ * marked command document based on the caller's schema. If successful, the
+ * state will be changed via @ref _mongo_done_markings().
+ *
+ * The purpose of this function is to short-circuit the phase of encryption
+ * wherein we would normally return to the driver and give them the opportunity
+ * to generate the markings by passing a special command to a mongocryptd daemon
+ * process. Instead, we'll do it ourselves here, if possible.
+ */
+static bool
+_try_run_csfle_marking (mongocrypt_ctx_t *ctx)
+{
+   BSON_ASSERT_PARAM (ctx);
+
+   BSON_ASSERT (
+      ctx->state == MONGOCRYPT_CTX_NEED_MONGO_MARKINGS &&
+      "_try_run_csfle_marking() should only be called when mongocrypt is "
+      "ready for markings");
+
+   _mongocrypt_ctx_encrypt_t *ectx = (_mongocrypt_ctx_encrypt_t *) ctx;
+
+   BSON_ASSERT (ctx->crypt);
+
+   // We have a valid schema and just need to mark the fields for encryption
+   if (!ctx->crypt->csfle.okay) {
+      // We don't have a csfle library to use to obtain the markings. It's up to
+      // caller to resolve them.
+      return true;
+   }
+
+   _mongo_crypt_v1_vtable csfle = ctx->crypt->csfle;
+   mongo_crypt_v1_lib *csfle_lib = ctx->crypt->csfle_lib;
+   BSON_ASSERT (csfle_lib);
+   bool okay = false;
+
+   // Obtain the command for markings
+   bson_t cmd = BSON_INITIALIZER;
+   if (!_create_markings_cmd_bson (ctx, &cmd)) {
+      goto fail_create_cmd;
+   }
+
+   const char *cmd_name = ectx->cmd_name;
+
+   if (!_add_dollar_db (cmd_name, &cmd, ectx->db_name, ctx->status)) {
+      _mongocrypt_ctx_fail (ctx);
+      goto fail_create_cmd;
+   }
+
+#define CHECK_CSFLE_ERROR(Func, FailLabel)                             \
+   if (1) {                                                            \
+      if (csfle.status_get_error (status)) {                           \
+         _mongocrypt_set_error (ctx->status,                           \
+                                MONGOCRYPT_STATUS_ERROR_CRYPT_SHARED,  \
+                                MONGOCRYPT_GENERIC_ERROR_CODE,         \
+                                "csfle " #Func                         \
+                                " failed: %s [Error %d, code %d]",     \
+                                csfle.status_get_explanation (status), \
+                                csfle.status_get_error (status),       \
+                                csfle.status_get_code (status));       \
+         _mongocrypt_ctx_fail (ctx);                                   \
+         goto FailLabel;                                               \
+      }                                                                \
+   } else                                                              \
+      ((void) 0)
+
+   mongo_crypt_v1_status *status = csfle.status_create ();
+   BSON_ASSERT (status);
+
+   mongo_crypt_v1_query_analyzer *qa =
+      csfle.query_analyzer_create (csfle_lib, status);
+   CHECK_CSFLE_ERROR ("query_analyzer_create", fail_qa_create);
+
+   uint32_t marked_bson_len = 0;
+   uint8_t *marked_bson = csfle.analyze_query (qa,
+                                               bson_get_data (&cmd),
+                                               ectx->ns,
+                                               (uint32_t) strlen (ectx->ns),
+                                               &marked_bson_len,
+                                               status);
+   CHECK_CSFLE_ERROR ("analyze_query", fail_analyze_query);
+
+   // Copy out the marked document.
+   mongocrypt_binary_t *marked =
+      mongocrypt_binary_new_from_data (marked_bson, marked_bson_len);
+   if (!_mongo_feed_markings (ctx, marked)) {
+      // Wrap error with additional information.
+      _mongocrypt_set_error (
+         ctx->status,
+         MONGOCRYPT_STATUS_ERROR_CLIENT,
+         MONGOCRYPT_GENERIC_ERROR_CODE,
+         "Consuming the generated csfle markings failed: %s",
+         mongocrypt_status_message (ctx->status, NULL /* len */));
+      goto fail_feed_markings;
+   }
+
+   okay = _mongo_done_markings (ctx);
+   if (!okay) {
+      // Wrap error with additional information.
+      _mongocrypt_set_error (
+         ctx->status,
+         MONGOCRYPT_STATUS_ERROR_CLIENT,
+         MONGOCRYPT_GENERIC_ERROR_CODE,
+         "Finalizing the generated csfle markings failed: %s",
+         mongocrypt_status_message (ctx->status, NULL /* len */));
+   }
+
+fail_feed_markings:
+   mongocrypt_binary_destroy (marked);
+   csfle.bson_free (marked_bson);
+fail_analyze_query:
+   csfle.query_analyzer_destroy (qa);
+fail_qa_create:
+   csfle.status_destroy (status);
+fail_create_cmd:
+   bson_destroy (&cmd);
+   return okay;
+}
+
+
+static bool
+_marking_to_bson_value (void *ctx,
+                        _mongocrypt_marking_t *marking,
+                        bson_value_t *out,
+                        mongocrypt_status_t *status)
+{
+   _mongocrypt_ciphertext_t ciphertext;
+   _mongocrypt_buffer_t serialized_ciphertext = {0};
+   bool ret = false;
+
+   BSON_ASSERT_PARAM (ctx);
+   BSON_ASSERT_PARAM (marking);
+   BSON_ASSERT_PARAM (out);
+
+   _mongocrypt_ciphertext_init (&ciphertext);
+
+   if (!_mongocrypt_marking_to_ciphertext (ctx, marking, &ciphertext, status)) {
+      goto fail;
+   }
+
+   if ((ciphertext.blob_subtype == MC_SUBTYPE_FLE2InsertUpdatePayload) ||
+       (ciphertext.blob_subtype == MC_SUBTYPE_FLE2FindEqualityPayload) ||
+       (ciphertext.blob_subtype == MC_SUBTYPE_FLE2FindRangePayload)) {
+      /* ciphertext_data is already a BSON object, just need to prepend
+       * blob_subtype */
+      if (ciphertext.data.len > UINT32_MAX - 1u) {
+         CLIENT_ERR ("ciphertext too long");
+         goto fail;
+      }
+      _mongocrypt_buffer_init_size (&serialized_ciphertext,
+                                    ciphertext.data.len + 1);
+      /* ciphertext->blob_subtype is an enum and easily fits in uint8_t */
+      serialized_ciphertext.data[0] = (uint8_t) ciphertext.blob_subtype;
+      memcpy (serialized_ciphertext.data + 1,
+              ciphertext.data.data,
+              ciphertext.data.len);
+
+   } else if (!_mongocrypt_serialize_ciphertext (&ciphertext,
+                                                 &serialized_ciphertext)) {
+      CLIENT_ERR ("malformed ciphertext");
+      goto fail;
+   };
+
+   /* ownership of serialized_ciphertext is transferred to caller. */
+   out->value_type = BSON_TYPE_BINARY;
+   out->value.v_binary.data = serialized_ciphertext.data;
+   out->value.v_binary.data_len = serialized_ciphertext.len;
+   out->value.v_binary.subtype = (bson_subtype_t) BSON_SUBTYPE_ENCRYPTED;
+
+   ret = true;
+
+fail:
+   _mongocrypt_ciphertext_cleanup (&ciphertext);
+   return ret;
+}
+
+
+static bool
+_replace_marking_with_ciphertext (void *ctx,
+                                  _mongocrypt_buffer_t *in,
+                                  bson_value_t *out,
+                                  mongocrypt_status_t *status)
+{
+   _mongocrypt_marking_t marking;
+   bool ret;
+
+   BSON_ASSERT_PARAM (ctx);
+   BSON_ASSERT_PARAM (in);
+
+   memset (&marking, 0, sizeof (marking));
+
+   if (!_mongocrypt_marking_parse_unowned (in, &marking, status)) {
+      _mongocrypt_marking_cleanup (&marking);
+      return false;
+   }
+
+   ret = _marking_to_bson_value (ctx, &marking, out, status);
+   _mongocrypt_marking_cleanup (&marking);
+   return ret;
+}
+
+
+/* generate_delete_tokens generates the 'deleteTokens' document to be appended
+ * to 'encryptionInformation'. */
+static bson_t *
+generate_delete_tokens (_mongocrypt_crypto_t *crypto,
+                        _mongocrypt_key_broker_t *kb,
+                        mc_EncryptedFieldConfig_t *efc,
+                        mongocrypt_status_t *status)
+{
+   bool ret = false;
+   bson_t *out = bson_new ();
+   mc_EncryptedField_t *ef;
+
+   BSON_ASSERT_PARAM (crypto);
+   BSON_ASSERT_PARAM (kb);
+   BSON_ASSERT_PARAM (efc);
+
+   for (ef = efc->fields; ef != NULL; ef = ef->next) {
+      _mongocrypt_buffer_t IndexKey = {0};
+      _mongocrypt_buffer_t TokenKey = {0};
+      mc_ServerDataEncryptionLevel1Token_t *sdel1t = NULL;
+      mc_CollectionsLevel1Token_t *cl1t = NULL;
+      mc_ECOCToken_t *ecoc = NULL;
+      bool loop_ok = false;
+      /* deleteTokens are only necessary for indexed fields. */
+      if (!ef->has_queries) {
+         goto loop_continue;
+      }
+
+      if (!_mongocrypt_key_broker_decrypted_key_by_id (
+             kb, &ef->keyId, &IndexKey)) {
+         _mongocrypt_key_broker_status (kb, status);
+         goto loop_fail;
+      }
+
+      /* Get the TokenKey from the last 32 bytes of IndexKey */
+      if (IndexKey.len < MONGOCRYPT_TOKEN_KEY_LEN) {
+         CLIENT_ERR ("IndexKey too short");
+         goto loop_fail;
+      }
+      if (!_mongocrypt_buffer_from_subrange (&TokenKey,
+                                             &IndexKey,
+                                             IndexKey.len -
+                                                MONGOCRYPT_TOKEN_KEY_LEN,
+                                             MONGOCRYPT_TOKEN_KEY_LEN)) {
+         CLIENT_ERR (
+            "generate_delete_tokens unable to parse TokenKey from IndexKey");
+         goto loop_fail;
+      }
+
+      sdel1t =
+         mc_ServerDataEncryptionLevel1Token_new (crypto, &TokenKey, status);
+      if (!sdel1t) {
+         goto loop_fail;
+      }
+
+      cl1t = mc_CollectionsLevel1Token_new (crypto, &TokenKey, status);
+      if (!cl1t) {
+         goto loop_fail;
+      }
+
+      ecoc = mc_ECOCToken_new (crypto, cl1t, status);
+      if (!ecoc) {
+         goto loop_fail;
+      }
+
+      bson_t field_bson;
+      if (!BSON_APPEND_DOCUMENT_BEGIN (out, ef->path, &field_bson)) {
+         CLIENT_ERR ("failed to begin document for 'deleteTokens.%s'",
+                     ef->path);
+         goto loop_fail;
+      }
+
+      if (!BSON_APPEND_BINARY (
+             &field_bson,
+             "e",
+             BSON_SUBTYPE_BINARY,
+             mc_ServerDataEncryptionLevel1Token_get (sdel1t)->data,
+             mc_ServerDataEncryptionLevel1Token_get (sdel1t)->len)) {
+         CLIENT_ERR ("failed to append ServerDataEncryptionLevel1Token for %s",
+                     ef->path);
+         goto loop_fail;
+      }
+
+      if (!BSON_APPEND_BINARY (&field_bson,
+                               "o",
+                               BSON_SUBTYPE_BINARY,
+                               mc_ECOCToken_get (ecoc)->data,
+                               mc_ECOCToken_get (ecoc)->len)) {
+         CLIENT_ERR ("failed to append ECOCToken for %s", ef->path);
+         goto loop_fail;
+      }
+
+      if (!bson_append_document_end (out, &field_bson)) {
+         CLIENT_ERR ("failed to end document for 'deleteTokens.%s'", ef->path);
+         goto loop_fail;
+      }
+
+   loop_continue:
+      loop_ok = true;
+   loop_fail:
+      _mongocrypt_buffer_cleanup (&IndexKey);
+      _mongocrypt_buffer_cleanup (&TokenKey);
+      mc_ServerDataEncryptionLevel1Token_destroy (sdel1t);
+      mc_CollectionsLevel1Token_destroy (cl1t);
+      mc_ECOCToken_destroy (ecoc);
+      if (!loop_ok) {
+         goto fail;
+      }
+   }
+
+   ret = true;
+fail:
+   if (!ret) {
+      bson_destroy (out);
+      return NULL;
+   }
+   return out;
+}
+
+static bool
+_check_for_payload_requiring_encryptionInformation (void *ctx,
+                                                    _mongocrypt_buffer_t *in,
+                                                    mongocrypt_status_t *status)
+{
+   bool *out = (bool *) ctx;
+
+   BSON_ASSERT_PARAM (ctx);
+   BSON_ASSERT_PARAM (in);
+
+   if (in->len < 1) {
+      CLIENT_ERR ("unexpected empty FLE payload");
+      return false;
+   }
+
+   if (in->data[0] == MC_SUBTYPE_FLE2InsertUpdatePayload) {
+      *out = true;
+      return true;
+   }
+
+   if (in->data[0] == MC_SUBTYPE_FLE2FindEqualityPayload) {
+      *out = true;
+      return true;
+   }
+
+   if (in->data[0] == MC_SUBTYPE_FLE2FindRangePayload) {
+      *out = true;
+      return true;
+   }
+
+   return true;
+}
+
+typedef struct {
+   bool must_omit;
+   bool ok;
+} moe_result;
+
+// must_omit_encryptionInformation returns true if the command
+// must omit the "encryptionInformation" field when sent to mongod / mongos.
+static moe_result
+must_omit_encryptionInformation (const char *command_name,
+                                 const bson_t *command,
+                                 mongocrypt_status_t *status)
+{
+   // eligible_commands may omit encryptionInformation if the command does not
+   // contain payloads requiring encryption.
+   const char *eligible_commands[] = {
+      "find", "aggregate", "distinct", "count", "insert"};
+   size_t i;
+   bool found = false;
+
+   // prohibited_commands prohibit encryptionInformation on mongod / mongos.
+   const char *prohibited_commands[] = {
+      "compactStructuredEncryptionData", "create", "collMod", "createIndexes"};
+
+   BSON_ASSERT_PARAM (command_name);
+   BSON_ASSERT_PARAM (command);
+
+   for (i = 0;
+        i < sizeof (prohibited_commands) / sizeof (prohibited_commands[0]);
+        i++) {
+      if (0 == strcmp (prohibited_commands[i], command_name)) {
+         return (moe_result){.ok = true, .must_omit = true};
+      }
+   }
+
+   for (i = 0; i < sizeof (eligible_commands) / sizeof (eligible_commands[0]);
+        i++) {
+      if (0 == strcmp (eligible_commands[i], command_name)) {
+         found = true;
+         break;
+      }
+   }
+   if (!found) {
+      return (moe_result){.ok = true};
+   }
+
+   bool has_payload_requiring_encryptionInformation = false;
+   bson_iter_t iter;
+   if (!bson_iter_init (&iter, command)) {
+      CLIENT_ERR ("unable to iterate command");
+      return (moe_result){.ok = false};
+   }
+   if (!_mongocrypt_traverse_binary_in_bson (
+          _check_for_payload_requiring_encryptionInformation,
+          &has_payload_requiring_encryptionInformation,
+          TRAVERSE_MATCH_SUBTYPE6,
+          &iter,
+          status)) {
+      return (moe_result){.ok = false};
+   }
+
+   if (!has_payload_requiring_encryptionInformation) {
+      return (moe_result){.ok = true, .must_omit = true};
+   }
+   return (moe_result){.ok = true, .must_omit = false};
+}
+
+/* _fle2_append_compactionTokens appends compactionTokens if command_name is
+ * "compactStructuredEncryptionData" */
+static bool
+_fle2_append_compactionTokens (_mongocrypt_crypto_t *crypto,
+                               _mongocrypt_key_broker_t *kb,
+                               mc_EncryptedFieldConfig_t *efc,
+                               const char *command_name,
+                               bson_t *out,
+                               mongocrypt_status_t *status)
+{
+   bson_t result_compactionTokens;
+   bool ret = false;
+
+   BSON_ASSERT_PARAM (crypto);
+   BSON_ASSERT_PARAM (kb);
+   BSON_ASSERT_PARAM (efc);
+   BSON_ASSERT_PARAM (command_name);
+   BSON_ASSERT_PARAM (out);
+
+   if (0 != strcmp (command_name, "compactStructuredEncryptionData")) {
+      return true;
+   }
+
+   BSON_APPEND_DOCUMENT_BEGIN (
+      out, "compactionTokens", &result_compactionTokens);
+
+   mc_EncryptedField_t *ptr;
+   for (ptr = efc->fields; ptr != NULL; ptr = ptr->next) {
+      /* Append ECOC token. */
+      _mongocrypt_buffer_t key = {0};
+      _mongocrypt_buffer_t tokenkey = {0};
+      mc_CollectionsLevel1Token_t *cl1t = NULL;
+      mc_ECOCToken_t *ecoct = NULL;
+      bool ecoc_ok = false;
+
+      if (!_mongocrypt_key_broker_decrypted_key_by_id (kb, &ptr->keyId, &key)) {
+         _mongocrypt_key_broker_status (kb, status);
+         goto ecoc_fail;
+      }
+      /* The last 32 bytes of the user key are the token key. */
+      if (key.len < MONGOCRYPT_TOKEN_KEY_LEN) {
+         CLIENT_ERR ("key too short");
+         goto ecoc_fail;
+      }
+      if (!_mongocrypt_buffer_from_subrange (&tokenkey,
+                                             &key,
+                                             key.len - MONGOCRYPT_TOKEN_KEY_LEN,
+                                             MONGOCRYPT_TOKEN_KEY_LEN)) {
+         CLIENT_ERR ("unable to get TokenKey from Data Encryption Key");
+         goto ecoc_fail;
+      }
+      cl1t = mc_CollectionsLevel1Token_new (crypto, &tokenkey, status);
+      if (!cl1t) {
+         goto ecoc_fail;
+      }
+
+      ecoct = mc_ECOCToken_new (crypto, cl1t, status);
+      if (!ecoct) {
+         goto ecoc_fail;
+      }
+
+      const _mongocrypt_buffer_t *ecoct_buf = mc_ECOCToken_get (ecoct);
+
+      BSON_APPEND_BINARY (&result_compactionTokens,
+                          ptr->path,
+                          BSON_SUBTYPE_BINARY,
+                          ecoct_buf->data,
+                          ecoct_buf->len);
+
+      ecoc_ok = true;
+   ecoc_fail:
+      mc_ECOCToken_destroy (ecoct);
+      mc_CollectionsLevel1Token_destroy (cl1t);
+      _mongocrypt_buffer_cleanup (&key);
+      if (!ecoc_ok) {
+         goto fail;
+      }
+   }
+
+   bson_append_document_end (out, &result_compactionTokens);
+
+   ret = true;
+fail:
+   return ret;
+}
+
+
+/**
+ * @brief Removes "encryptionInformation" from cmd.
+ */
+static bool
+_fle2_strip_encryptionInformation (const char *cmd_name,
+                                   bson_t *cmd /* in and out */,
+                                   mongocrypt_status_t *status)
+{
+   bson_t stripped = BSON_INITIALIZER;
+   bool ok = false;
+
+   BSON_ASSERT_PARAM (cmd_name);
+   BSON_ASSERT_PARAM (cmd);
+
+   if (0 != strcmp (cmd_name, "explain")) {
+      bson_copy_to_excluding_noinit (
+         cmd, &stripped, "encryptionInformation", NULL);
+      goto success;
+   }
+
+   // The 'explain' command is a special case.
+   // 'encryptionInformation' is returned from mongocryptd and csfle nested
+   // inside 'explain'. Example:
+   // {
+   //    "explain": {
+   //       "find": "coll"
+   //       "encryptionInformation": {}
+   //    }
+   // }
+   bson_iter_t iter;
+   bson_t explain;
+
+   BSON_ASSERT (bson_iter_init_find (&iter, cmd, "explain"));
+   if (!BSON_ITER_HOLDS_DOCUMENT (&iter)) {
+      CLIENT_ERR ("expected 'explain' to be document");
+      goto fail;
+   }
+
+   {
+      bson_t tmp;
+      if (!mc_iter_document_as_bson (&iter, &tmp, status)) {
+         goto fail;
+      }
+      bson_init (&explain);
+      bson_copy_to_excluding_noinit (
+         &tmp, &explain, "encryptionInformation", NULL);
+   }
+
+   if (!BSON_APPEND_DOCUMENT (&stripped, "explain", &explain)) {
+      bson_destroy (&explain);
+      CLIENT_ERR ("unable to append 'explain'");
+      goto fail;
+   }
+   bson_destroy (&explain);
+   bson_copy_to_excluding_noinit (cmd, &stripped, "explain", NULL);
+
+success:
+   bson_destroy (cmd);
+   if (!bson_steal (cmd, &stripped)) {
+      CLIENT_ERR ("failed to steal BSON without encryptionInformation");
+      goto fail;
+   }
+   ok = true;
+fail:
+   if (!ok) {
+      bson_destroy (&stripped);
+   }
+   return ok;
+}
+
+/* Process a call to mongocrypt_ctx_finalize when an encryptedFieldConfig is
+ * associated with the command. */
+static bool
+_fle2_finalize (mongocrypt_ctx_t *ctx, mongocrypt_binary_t *out)
+{
+   bson_t converted;
+   _mongocrypt_ctx_encrypt_t *ectx;
+   bson_t encrypted_field_config_bson;
+   bson_t original_cmd_bson;
+
+   BSON_ASSERT_PARAM (ctx);
+   BSON_ASSERT_PARAM (out);
+
+   ectx = (_mongocrypt_ctx_encrypt_t *) ctx;
+
+   BSON_ASSERT (context_uses_fle2 (ctx));
+   BSON_ASSERT (ctx->state == MONGOCRYPT_CTX_READY);
+
+   if (ectx->explicit) {
+      return _mongocrypt_ctx_fail_w_msg (
+         ctx, "explicit encryption is not yet supported. See MONGOCRYPT-409.");
+   }
+
+   if (!_mongocrypt_buffer_to_bson (&ectx->encrypted_field_config,
+                                    &encrypted_field_config_bson)) {
+      return _mongocrypt_ctx_fail_w_msg (
+         ctx, "malformed bson in encrypted_field_config_bson");
+   }
+
+   if (!_mongocrypt_buffer_to_bson (&ectx->original_cmd, &original_cmd_bson)) {
+      return _mongocrypt_ctx_fail_w_msg (ctx, "malformed bson in original_cmd");
+   }
+
+   /* If marked_cmd buffer is empty, there are no markings to encrypt. */
+   if (_mongocrypt_buffer_empty (&ectx->marked_cmd)) {
+      /* Append 'encryptionInformation' to the original command. */
+      bson_copy_to (&original_cmd_bson, &converted);
+   } else {
+      bson_t as_bson;
+      bson_iter_t iter;
+
+      if (!_mongocrypt_buffer_to_bson (&ectx->marked_cmd, &as_bson)) {
+         return _mongocrypt_ctx_fail_w_msg (ctx, "malformed bson");
+      }
+
+      bson_iter_init (&iter, &as_bson);
+      bson_init (&converted);
+      if (!_mongocrypt_transform_binary_in_bson (
+             _replace_marking_with_ciphertext,
+             &ctx->kb,
+             TRAVERSE_MATCH_MARKING,
+             &iter,
+             &converted,
+             ctx->status)) {
+         bson_destroy (&converted);
+         return _mongocrypt_ctx_fail (ctx);
+      }
+   }
+
+   const char *command_name = ectx->cmd_name;
+
+   /* Remove the 'encryptionInformation' field. It is appended in the response
+    * from mongocryptd or csfle. */
+   if (!_fle2_strip_encryptionInformation (
+          command_name, &converted, ctx->status)) {
+      bson_destroy (&converted);
+      return _mongocrypt_ctx_fail (ctx);
+   }
+
+   bson_t *deleteTokens = NULL;
+   if (command_needs_deleteTokens (command_name)) {
+      deleteTokens = generate_delete_tokens (
+         ctx->crypt->crypto, &ctx->kb, &ectx->efc, ctx->status);
+      if (!deleteTokens) {
+         bson_destroy (&converted);
+         return _mongocrypt_ctx_fail (ctx);
+      }
+   }
+
+   moe_result result =
+      must_omit_encryptionInformation (command_name, &converted, ctx->status);
+   if (!result.ok) {
+      bson_destroy (&converted);
+      bson_destroy (deleteTokens);
+      return _mongocrypt_ctx_fail (ctx);
+   }
+
+   /* Append a new 'encryptionInformation'. */
+   if (!result.must_omit) {
+      if (!_fle2_insert_encryptionInformation (command_name,
+                                               &converted,
+                                               ectx->ns,
+                                               &encrypted_field_config_bson,
+                                               deleteTokens,
+                                               ectx->coll_name,
+                                               MC_TO_MONGOD,
+                                               ctx->status)) {
+         bson_destroy (&converted);
+         bson_destroy (deleteTokens);
+         return _mongocrypt_ctx_fail (ctx);
+      }
+   }
+   bson_destroy (deleteTokens);
+
+   if (!_fle2_append_compactionTokens (ctx->crypt->crypto,
+                                       &ctx->kb,
+                                       &ectx->efc,
+                                       command_name,
+                                       &converted,
+                                       ctx->status)) {
+      bson_destroy (&converted);
+      return _mongocrypt_ctx_fail (ctx);
+   }
+
+   // If input command has $db, ensure output command has $db.
+   bson_iter_t iter;
+   if (bson_iter_init_find (&iter, &original_cmd_bson, "$db")) {
+      if (!bson_iter_init_find (&iter, &converted, "$db")) {
+         BSON_APPEND_UTF8 (&converted, "$db", ectx->db_name);
+      }
+   }
+
+   _mongocrypt_buffer_steal_from_bson (&ectx->encrypted_cmd, &converted);
+   _mongocrypt_buffer_to_binary (&ectx->encrypted_cmd, out);
+   ctx->state = MONGOCRYPT_CTX_DONE;
+
+   return true;
+}
+
+static bool
+FLE2RangeFindDriverSpec_to_ciphertexts (mongocrypt_ctx_t *ctx,
+                                        mongocrypt_binary_t *out)
+{
+   bool ok = false;
+   _mongocrypt_ctx_encrypt_t *ectx = (_mongocrypt_ctx_encrypt_t *) ctx;
+
+   BSON_ASSERT_PARAM (ctx);
+   BSON_ASSERT_PARAM (out);
+
+   if (!ctx->opts.rangeopts.set) {
+      _mongocrypt_ctx_fail_w_msg (
+         ctx, "Expected RangeOpts to be set for Range Find");
+      goto fail;
+   }
+   if (!ctx->opts.contention_factor.set) {
+      _mongocrypt_ctx_fail_w_msg (
+         ctx, "Expected Contention Factor to be set for Range Find");
+      goto fail;
+   }
+
+   bson_t with_placholders = BSON_INITIALIZER;
+   bson_t with_ciphertexts = BSON_INITIALIZER;
+   bson_t in_bson;
+   if (!_mongocrypt_buffer_to_bson (&ectx->original_cmd, &in_bson)) {
+      _mongocrypt_ctx_fail_w_msg (ctx, "unable to convert input to BSON");
+      goto fail;
+   }
+
+   bson_t v_doc;
+   // Parse 'v' document from input.
+   {
+      bson_iter_t v_iter;
+      if (!bson_iter_init_find (&v_iter, &in_bson, "v")) {
+         _mongocrypt_ctx_fail_w_msg (ctx,
+                                     "invalid input BSON, must contain 'v'");
+         goto fail;
+      }
+      if (!BSON_ITER_HOLDS_DOCUMENT (&v_iter)) {
+         _mongocrypt_ctx_fail_w_msg (
+            ctx, "invalid input BSON, expected 'v' to be document");
+         goto fail;
+      }
+      if (!mc_iter_document_as_bson (&v_iter, &v_doc, ctx->status)) {
+         _mongocrypt_ctx_fail (ctx);
+         goto fail;
+      }
+   }
+
+   // Parse FLE2RangeFindDriverSpec.
+   {
+      mc_FLE2RangeFindDriverSpec_t rfds;
+
+      if (!mc_FLE2RangeFindDriverSpec_parse (&rfds, &v_doc, ctx->status)) {
+         _mongocrypt_ctx_fail (ctx);
+         goto fail;
+      }
+
+      // Convert FLE2RangeFindDriverSpec into a document with placeholders.
+      if (!mc_FLE2RangeFindDriverSpec_to_placeholders (
+             &rfds,
+             &ctx->opts.rangeopts.value,
+             ctx->opts.contention_factor.value,
+             &ctx->opts.key_id,
+             _mongocrypt_buffer_empty (&ctx->opts.index_key_id)
+                ? &ctx->opts.key_id
+                : &ctx->opts.index_key_id,
+             mc_getNextPayloadId (),
+             &with_placholders,
+             ctx->status)) {
+         _mongocrypt_ctx_fail (ctx);
+         goto fail;
+      }
+   }
+
+   // Convert document with placeholders into document with ciphertexts.
+   {
+      bson_iter_t iter;
+      if (!bson_iter_init (&iter, &with_placholders)) {
+         _mongocrypt_ctx_fail_w_msg (
+            ctx, "unable to iterate into placeholder document");
+         goto fail;
+      }
+      if (!_mongocrypt_transform_binary_in_bson (
+             _replace_marking_with_ciphertext,
+             &ctx->kb,
+             TRAVERSE_MATCH_MARKING,
+             &iter,
+             &with_ciphertexts,
+             ctx->status)) {
+         goto fail;
+      }
+   }
+
+   // Wrap result in the document: { 'v': <result> }.
+   {
+      /* v_wrapped is the BSON document { 'v': <v_out> }. */
+      bson_t v_wrapped = BSON_INITIALIZER;
+      if (!bson_append_document (
+             &v_wrapped, MONGOCRYPT_STR_AND_LEN ("v"), &with_ciphertexts)) {
+         _mongocrypt_ctx_fail_w_msg (ctx, "unable to append document to 'v'");
+         goto fail;
+      }
+      _mongocrypt_buffer_steal_from_bson (&ectx->encrypted_cmd, &v_wrapped);
+      _mongocrypt_buffer_to_binary (&ectx->encrypted_cmd, out);
+      ctx->state = MONGOCRYPT_CTX_DONE;
+   }
+
+   ok = true;
+fail:
+   bson_destroy (&with_ciphertexts);
+   bson_destroy (&with_placholders);
+   return ok;
+}
+
+static bool
+_fle2_finalize_explicit (mongocrypt_ctx_t *ctx, mongocrypt_binary_t *out)
+{
+   bool ret = false;
+   _mongocrypt_marking_t marking;
+   _mongocrypt_ctx_encrypt_t *ectx = (_mongocrypt_ctx_encrypt_t *) ctx;
+
+   BSON_ASSERT_PARAM (ctx);
+   BSON_ASSERT_PARAM (out);
+
+   BSON_ASSERT (ctx->opts.index_type.set);
+
+   if (ctx->opts.rangeopts.set && ctx->opts.query_type.set) {
+      // RangeOpts with query type is a special case. The result contains two
+      // ciphertext values.
+      return FLE2RangeFindDriverSpec_to_ciphertexts (ctx, out);
+   }
+
+   bson_t new_v = BSON_INITIALIZER;
+
+   _mongocrypt_marking_init (&marking);
+   marking.type = MONGOCRYPT_MARKING_FLE2_ENCRYPTION;
+   if (ctx->opts.query_type.set) {
+      switch (ctx->opts.query_type.value) {
+      case MONGOCRYPT_QUERY_TYPE_RANGEPREVIEW:
+      case MONGOCRYPT_QUERY_TYPE_EQUALITY:
+         marking.fle2.type = MONGOCRYPT_FLE2_PLACEHOLDER_TYPE_FIND;
+         break;
+      default:
+         _mongocrypt_ctx_fail_w_msg (ctx,
+                                     "Invalid value for EncryptOpts.queryType");
+         goto fail;
+      }
+   } else {
+      marking.fle2.type = MONGOCRYPT_FLE2_PLACEHOLDER_TYPE_INSERT;
+   }
+
+   switch (ctx->opts.index_type.value) {
+   case MONGOCRYPT_INDEX_TYPE_EQUALITY:
+      marking.fle2.algorithm = MONGOCRYPT_FLE2_ALGORITHM_EQUALITY;
+      break;
+   case MONGOCRYPT_INDEX_TYPE_NONE:
+      marking.fle2.algorithm = MONGOCRYPT_FLE2_ALGORITHM_UNINDEXED;
+      break;
+   case MONGOCRYPT_INDEX_TYPE_RANGEPREVIEW:
+      marking.fle2.algorithm = MONGOCRYPT_FLE2_ALGORITHM_RANGE;
+      break;
+   default:
+      // This might be unreachable because of other validation. Better safe than
+      // sorry.
+      _mongocrypt_ctx_fail_w_msg (ctx,
+                                  "Invalid value for EncryptOpts.indexType");
+      goto fail;
+   }
+
+   if (ctx->opts.rangeopts.set) {
+      // Process the RangeOpts and the input 'v' document into a new 'v'.
+      // The new 'v' document will be a FLE2RangeFindSpec or
+      // FLE2RangeInsertSpec.
+      bson_t old_v;
+
+      if (!_mongocrypt_buffer_to_bson (&ectx->original_cmd, &old_v)) {
+         _mongocrypt_ctx_fail_w_msg (ctx, "unable to convert input to BSON");
+         goto fail;
+      }
+
+      // RangeOpts with query_type is handled above.
+      BSON_ASSERT (!ctx->opts.query_type.set);
+      if (!mc_RangeOpts_to_FLE2RangeInsertSpec (
+             &ctx->opts.rangeopts.value, &old_v, &new_v, ctx->status)) {
+         _mongocrypt_ctx_fail (ctx);
+         goto fail;
+      }
+
+
+      if (!bson_iter_init_find (&marking.v_iter, &new_v, "v")) {
+         _mongocrypt_ctx_fail_w_msg (ctx,
+                                     "invalid input BSON, must contain 'v'");
+         goto fail;
+      }
+
+      marking.fle2.sparsity = ctx->opts.rangeopts.value.sparsity;
+
+   } else {
+      bson_t as_bson;
+
+      /* Get iterator to input 'v' BSON value. */
+      if (!_mongocrypt_buffer_to_bson (&ectx->original_cmd, &as_bson)) {
+         _mongocrypt_ctx_fail_w_msg (ctx, "unable to convert input to BSON");
+         goto fail;
+      }
+
+      if (!bson_iter_init_find (&marking.v_iter, &as_bson, "v")) {
+         _mongocrypt_ctx_fail_w_msg (ctx,
+                                     "invalid input BSON, must contain 'v'");
+         goto fail;
+      }
+   }
+
+   _mongocrypt_buffer_copy_to (&ctx->opts.key_id, &marking.fle2.user_key_id);
+   if (!_mongocrypt_buffer_empty (&ctx->opts.index_key_id)) {
+      _mongocrypt_buffer_copy_to (&ctx->opts.index_key_id,
+                                  &marking.fle2.index_key_id);
+   } else {
+      _mongocrypt_buffer_copy_to (&ctx->opts.key_id,
+                                  &marking.fle2.index_key_id);
+   }
+
+   if (ctx->opts.contention_factor.set) {
+      marking.fle2.maxContentionCounter = ctx->opts.contention_factor.value;
+   } else if (ctx->opts.index_type.value == MONGOCRYPT_INDEX_TYPE_EQUALITY) {
+      _mongocrypt_ctx_fail_w_msg (
+         ctx, "contention factor required for indexed algorithm");
+      goto fail;
+   }
+
+   /* Convert marking to ciphertext. */
+   {
+      bson_value_t v_out;
+      /* v_wrapped is the BSON document { 'v': <v_out> }. */
+      bson_t v_wrapped = BSON_INITIALIZER;
+
+      if (!_marking_to_bson_value (&ctx->kb, &marking, &v_out, ctx->status)) {
+         bson_destroy (&v_wrapped);
+         _mongocrypt_ctx_fail (ctx);
+         goto fail;
+      }
+
+      bson_append_value (&v_wrapped, MONGOCRYPT_STR_AND_LEN ("v"), &v_out);
+      _mongocrypt_buffer_steal_from_bson (&ectx->encrypted_cmd, &v_wrapped);
+      _mongocrypt_buffer_to_binary (&ectx->encrypted_cmd, out);
+      ctx->state = MONGOCRYPT_CTX_DONE;
+      bson_value_destroy (&v_out);
+   }
+
+   ret = true;
+fail:
+   bson_destroy (&new_v);
+   _mongocrypt_marking_cleanup (&marking);
+   return ret;
+}
+
+static bool
+_finalize (mongocrypt_ctx_t *ctx, mongocrypt_binary_t *out)
+{
+   bson_t as_bson, converted;
+   bson_iter_t iter;
+   _mongocrypt_ctx_encrypt_t *ectx;
+   bool res;
+
+   BSON_ASSERT_PARAM (ctx);
+   BSON_ASSERT_PARAM (out);
+
+   ectx = (_mongocrypt_ctx_encrypt_t *) ctx;
+
+   if (context_uses_fle2 (ctx)) {
+      return _fle2_finalize (ctx, out);
+   } else if (ctx->opts.index_type.set) {
+      return _fle2_finalize_explicit (ctx, out);
+   }
+
+   if (!ectx->explicit) {
+      if (ctx->nothing_to_do) {
+         _mongocrypt_buffer_to_binary (&ectx->original_cmd, out);
+         ctx->state = MONGOCRYPT_CTX_DONE;
+         return true;
+      }
+      if (!_mongocrypt_buffer_to_bson (&ectx->marked_cmd, &as_bson)) {
+         return _mongocrypt_ctx_fail_w_msg (ctx, "malformed bson");
+      }
+
+      bson_iter_init (&iter, &as_bson);
+      bson_init (&converted);
+      if (!_mongocrypt_transform_binary_in_bson (
+             _replace_marking_with_ciphertext,
+             &ctx->kb,
+             TRAVERSE_MATCH_MARKING,
+             &iter,
+             &converted,
+             ctx->status)) {
+         bson_destroy (&converted);
+         return _mongocrypt_ctx_fail (ctx);
+      }
+
+      bson_t original_cmd_bson;
+      if (!_mongocrypt_buffer_to_bson (&ectx->original_cmd,
+                                       &original_cmd_bson)) {
+         return _mongocrypt_ctx_fail_w_msg (ctx,
+                                            "malformed bson in original_cmd");
+      }
+
+      // If input command has $db, ensure output command has $db.
+      bson_iter_t iter;
+      if (bson_iter_init_find (&iter, &original_cmd_bson, "$db")) {
+         if (!bson_iter_init_find (&iter, &converted, "$db")) {
+            BSON_APPEND_UTF8 (&converted, "$db", ectx->db_name);
+         }
+      }
+   } else {
+      /* For explicit encryption, we have no marking, but we can fake one */
+      _mongocrypt_marking_t marking;
+      bson_value_t value;
+
+      memset (&value, 0, sizeof (value));
+
+      _mongocrypt_marking_init (&marking);
+
+      if (!_mongocrypt_buffer_to_bson (&ectx->original_cmd, &as_bson)) {
+         return _mongocrypt_ctx_fail_w_msg (ctx, "malformed bson");
+      }
+
+      if (!bson_iter_init_find (&iter, &as_bson, "v")) {
+         return _mongocrypt_ctx_fail_w_msg (ctx,
+                                            "invalid msg, must contain 'v'");
+      }
+
+
+      memcpy (&marking.v_iter, &iter, sizeof (bson_iter_t));
+      marking.algorithm = ctx->opts.algorithm;
+      _mongocrypt_buffer_set_to (&ctx->opts.key_id, &marking.key_id);
+      if (ctx->opts.key_alt_names) {
+         bson_value_copy (&ctx->opts.key_alt_names->value,
+                          &marking.key_alt_name);
+         marking.type = MONGOCRYPT_MARKING_FLE1_BY_ALTNAME;
+      }
+
+      bson_init (&converted);
+      res = _marking_to_bson_value (&ctx->kb, &marking, &value, ctx->status);
+      if (res) {
+         bson_append_value (&converted, MONGOCRYPT_STR_AND_LEN ("v"), &value);
+      }
+
+      bson_value_destroy (&value);
+      _mongocrypt_marking_cleanup (&marking);
+
+      if (!res) {
+         bson_destroy (&converted);
+         return _mongocrypt_ctx_fail (ctx);
+      }
+   }
+
+   _mongocrypt_buffer_steal_from_bson (&ectx->encrypted_cmd, &converted);
+   _mongocrypt_buffer_to_binary (&ectx->encrypted_cmd, out);
+   ctx->state = MONGOCRYPT_CTX_DONE;
+
+   return true;
+}
+
+
+static void
+_cleanup (mongocrypt_ctx_t *ctx)
+{
+   _mongocrypt_ctx_encrypt_t *ectx;
+
+   if (!ctx) {
+      return;
+   }
+
+   ectx = (_mongocrypt_ctx_encrypt_t *) ctx;
+   bson_free (ectx->ns);
+   bson_free (ectx->db_name);
+   bson_free (ectx->coll_name);
+   _mongocrypt_buffer_cleanup (&ectx->list_collections_filter);
+   _mongocrypt_buffer_cleanup (&ectx->schema);
+   _mongocrypt_buffer_cleanup (&ectx->encrypted_field_config);
+   _mongocrypt_buffer_cleanup (&ectx->original_cmd);
+   _mongocrypt_buffer_cleanup (&ectx->mongocryptd_cmd);
+   _mongocrypt_buffer_cleanup (&ectx->marked_cmd);
+   _mongocrypt_buffer_cleanup (&ectx->encrypted_cmd);
+   _mongocrypt_buffer_cleanup (&ectx->ismaster.cmd);
+   mc_EncryptedFieldConfig_cleanup (&ectx->efc);
+}
+
+
+static bool
+_try_schema_from_schema_map (mongocrypt_ctx_t *ctx)
+{
+   mongocrypt_t *crypt;
+   _mongocrypt_ctx_encrypt_t *ectx;
+   bson_t schema_map;
+   bson_iter_t iter;
+
+   BSON_ASSERT_PARAM (ctx);
+
+   crypt = ctx->crypt;
+   ectx = (_mongocrypt_ctx_encrypt_t *) ctx;
+
+   if (_mongocrypt_buffer_empty (&crypt->opts.schema_map)) {
+      /* No schema map set. */
+      return true;
+   }
+
+   if (!_mongocrypt_buffer_to_bson (&crypt->opts.schema_map, &schema_map)) {
+      return _mongocrypt_ctx_fail_w_msg (ctx, "malformed schema map");
+   }
+
+   if (bson_iter_init_find (&iter, &schema_map, ectx->ns)) {
+      if (!_mongocrypt_buffer_copy_from_document_iter (&ectx->schema, &iter)) {
+         return _mongocrypt_ctx_fail_w_msg (ctx, "malformed schema map");
+      }
+      ectx->used_local_schema = true;
+      ctx->state = MONGOCRYPT_CTX_NEED_MONGO_MARKINGS;
+   }
+
+   /* No schema found in map. */
+   return true;
+}
+
+/* Check if the local encrypted field config map has an entry for this
+ * collection.
+ * If an encrypted field config is found, the context transitions to
+ * MONGOCRYPT_CTX_NEED_MONGO_MARKINGS. */
+static bool
+_fle2_try_encrypted_field_config_from_map (mongocrypt_ctx_t *ctx)
+{
+   mongocrypt_t *crypt;
+   _mongocrypt_ctx_encrypt_t *ectx;
+   bson_t encrypted_field_config_map;
+   bson_iter_t iter;
+
+   BSON_ASSERT_PARAM (ctx);
+
+   crypt = ctx->crypt;
+   ectx = (_mongocrypt_ctx_encrypt_t *) ctx;
+
+   if (_mongocrypt_buffer_empty (&crypt->opts.encrypted_field_config_map)) {
+      /* No encrypted_field_config_map set. */
+      return true;
+   }
+
+   if (!_mongocrypt_buffer_to_bson (&crypt->opts.encrypted_field_config_map,
+                                    &encrypted_field_config_map)) {
+      return _mongocrypt_ctx_fail_w_msg (
+         ctx, "unable to convert encrypted_field_config_map to BSON");
+   }
+
+   if (bson_iter_init_find (&iter, &encrypted_field_config_map, ectx->ns)) {
+      if (!_mongocrypt_buffer_copy_from_document_iter (
+             &ectx->encrypted_field_config, &iter)) {
+         return _mongocrypt_ctx_fail_w_msg (
+            ctx,
+            "unable to copy encrypted_field_config from "
+            "encrypted_field_config_map");
+      }
+      bson_t efc_bson;
+      if (!_mongocrypt_buffer_to_bson (&ectx->encrypted_field_config,
+                                       &efc_bson)) {
+         return _mongocrypt_ctx_fail_w_msg (
+            ctx, "unable to create BSON from encrypted_field_config");
+      }
+      if (!mc_EncryptedFieldConfig_parse (&ectx->efc, &efc_bson, ctx->status)) {
+         _mongocrypt_ctx_fail (ctx);
+         return false;
+      }
+      ctx->state = MONGOCRYPT_CTX_NEED_MONGO_MARKINGS;
+   }
+
+   /* No encrypted_field_config found in map. */
+   return true;
+}
+
+
+static bool
+_try_schema_from_cache (mongocrypt_ctx_t *ctx)
+{
+   _mongocrypt_ctx_encrypt_t *ectx;
+   bson_t *collinfo = NULL;
+
+   BSON_ASSERT_PARAM (ctx);
+
+   ectx = (_mongocrypt_ctx_encrypt_t *) ctx;
+
+   /* Otherwise, we need a remote schema. Check if we have a response to
+    * listCollections cached. */
+   if (!_mongocrypt_cache_get (&ctx->crypt->cache_collinfo,
+                               ectx->ns /* null terminated */,
+                               (void **) &collinfo)) {
+      return _mongocrypt_ctx_fail_w_msg (ctx, "failed to retrieve from cache");
+   }
+
+   if (collinfo) {
+      if (!_set_schema_from_collinfo (ctx, collinfo)) {
+         return _mongocrypt_ctx_fail (ctx);
+      }
+      ctx->state = MONGOCRYPT_CTX_NEED_MONGO_MARKINGS;
+   } else {
+      /* we need to get it. */
+      ctx->state = MONGOCRYPT_CTX_NEED_MONGO_COLLINFO;
+   }
+
+   bson_destroy (collinfo);
+   return true;
+}
+
+/* _try_empty_schema_for_create uses an empty JSON schema for the create
+ * command. This is to avoid an unnecessary 'listCollections' command for
+ * create. */
+static bool
+_try_empty_schema_for_create (mongocrypt_ctx_t *ctx)
+{
+   _mongocrypt_ctx_encrypt_t *ectx;
+
+   BSON_ASSERT_PARAM (ctx);
+
+   ectx = (_mongocrypt_ctx_encrypt_t *) ctx;
+   /* As a special case, use an empty schema for the 'create' command. */
+   const char *cmd_name = ectx->cmd_name;
+
+   if (0 != strcmp (cmd_name, "create")) {
+      return true;
+   }
+
+   bson_t empty = BSON_INITIALIZER;
+   _mongocrypt_buffer_steal_from_bson (&ectx->schema, &empty);
+   ctx->state = MONGOCRYPT_CTX_NEED_MONGO_MARKINGS;
+   return true;
+}
+
+/* _try_schema_from_create_or_collMod_cmd tries to find a JSON schema included
+ * in a create or collMod command by checking for "validator.$jsonSchema".
+ * Example:
+ * {
+ *     "create" : "coll",
+ *     "validator" : {
+ *         "$jsonSchema" : {
+ *             "properties" : { "a" : { "bsonType" : "number" } }
+ *          }
+ *     }
+ * }
+ * If the "create" command does not include a JSON schema, an empty JSON schema
+ * is returned. This is to avoid an unnecessary 'listCollections' command for
+ * create.
+ *
+ * If the "collMod" command does not include a JSON schema, a schema is later
+ * requested by entering the MONGOCRYPT_CTX_NEED_MONGO_COLLINFO state.
+ * This is because a "collMod" command may have sensitive data in the
+ * "validator" field.
+ */
+static bool
+_try_schema_from_create_or_collMod_cmd (mongocrypt_ctx_t *ctx)
+{
+   _mongocrypt_ctx_encrypt_t *ectx;
+   mongocrypt_status_t *status;
+
+   BSON_ASSERT_PARAM (ctx);
+
+   status = ctx->status;
+
+   ectx = (_mongocrypt_ctx_encrypt_t *) ctx;
+   const char *cmd_name = ectx->cmd_name;
+
+   if (0 != strcmp (cmd_name, "create") && 0 != strcmp (cmd_name, "collMod")) {
+      return true;
+   }
+
+   bson_t cmd_bson;
+   bson_iter_t iter;
+
+   if (!_mongocrypt_buffer_to_bson (&ectx->original_cmd, &cmd_bson)) {
+      CLIENT_ERR ("unable to convert command buffer to BSON");
+      _mongocrypt_ctx_fail (ctx);
+      return false;
+   }
+
+   if (!bson_iter_init (&iter, &cmd_bson)) {
+      CLIENT_ERR ("unable to iterate over command BSON");
+      _mongocrypt_ctx_fail (ctx);
+      return false;
+   }
+
+   if (bson_iter_find_descendant (&iter, "validator.$jsonSchema", &iter)) {
+      if (!_mongocrypt_buffer_copy_from_document_iter (&ectx->schema, &iter)) {
+         CLIENT_ERR (
+            "failed to parse BSON document from create validator.$jsonSchema");
+         _mongocrypt_ctx_fail (ctx);
+         return false;
+      }
+      ctx->state = MONGOCRYPT_CTX_NEED_MONGO_MARKINGS;
+      return true;
+   }
+
+   return true;
+}
+
+static bool
+_permitted_for_encryption (bson_iter_t *iter,
+                           mongocrypt_encryption_algorithm_t algo,
+                           mongocrypt_status_t *status)
+{
+   bson_type_t bson_type;
+   const bson_value_t *bson_value;
+   bool ret = false;
+
+   BSON_ASSERT_PARAM (iter);
+
+   bson_value = bson_iter_value (iter);
+   if (!bson_value) {
+      CLIENT_ERR ("Unknown BSON type");
+      goto fail;
+   }
+   bson_type = bson_value->value_type;
+   switch (bson_type) {
+   case BSON_TYPE_NULL:
+   case BSON_TYPE_MINKEY:
+   case BSON_TYPE_MAXKEY:
+   case BSON_TYPE_UNDEFINED:
+      CLIENT_ERR ("BSON type invalid for encryption");
+      goto fail;
+   case BSON_TYPE_BINARY:
+      if (bson_value->value.v_binary.subtype == BSON_SUBTYPE_ENCRYPTED) {
+         CLIENT_ERR ("BSON binary subtype 6 is invalid for encryption");
+         goto fail;
+      }
+      /* ok */
+      break;
+   case BSON_TYPE_DOUBLE:
+   case BSON_TYPE_DOCUMENT:
+   case BSON_TYPE_ARRAY:
+   case BSON_TYPE_CODEWSCOPE:
+   case BSON_TYPE_BOOL:
+   case BSON_TYPE_DECIMAL128:
+      if (algo == MONGOCRYPT_ENCRYPTION_ALGORITHM_DETERMINISTIC) {
+         CLIENT_ERR ("BSON type invalid for deterministic encryption");
+         goto fail;
+      }
+      break;
+   case BSON_TYPE_UTF8:
+   case BSON_TYPE_OID:
+   case BSON_TYPE_DATE_TIME:
+   case BSON_TYPE_REGEX:
+   case BSON_TYPE_DBPOINTER:
+   case BSON_TYPE_CODE:
+   case BSON_TYPE_SYMBOL:
+   case BSON_TYPE_INT32:
+   case BSON_TYPE_TIMESTAMP:
+   case BSON_TYPE_INT64:
+      /* ok */
+      break;
+   case BSON_TYPE_EOD:
+   default:
+      CLIENT_ERR ("invalid BSON value type 00");
+      goto fail;
+   }
+
+   ret = true;
+fail:
+   return ret;
+}
+
+// explicit_encrypt_init is common code shared by
+// mongocrypt_ctx_explicit_encrypt_init and
+// mongocrypt_ctx_explicit_encrypt_expression_init.
+static bool
+explicit_encrypt_init (mongocrypt_ctx_t *ctx, mongocrypt_binary_t *msg)
+{
+   _mongocrypt_ctx_encrypt_t *ectx;
+   bson_t as_bson;
+   bson_iter_t iter;
+   _mongocrypt_ctx_opts_spec_t opts_spec;
+
+   if (!ctx) {
+      return false;
+   }
+   memset (&opts_spec, 0, sizeof (opts_spec));
+   opts_spec.key_descriptor = OPT_REQUIRED;
+   opts_spec.algorithm = OPT_OPTIONAL;
+   opts_spec.rangeopts = OPT_OPTIONAL;
+
+   if (!_mongocrypt_ctx_init (ctx, &opts_spec)) {
+      return false;
+   }
+
+   /* Error if any mutually exclusive FLE 1 and FLE 2 options are set. */
+   {
+      /* key_alt_names is FLE 1 only. */
+      if (ctx->opts.key_alt_names != NULL) {
+         if (ctx->opts.index_type.set) {
+            return _mongocrypt_ctx_fail_w_msg (
+               ctx, "cannot set both key alt name and index type");
+         }
+         if (!_mongocrypt_buffer_empty (&ctx->opts.index_key_id)) {
+            return _mongocrypt_ctx_fail_w_msg (
+               ctx, "cannot set both key alt name and index key id");
+         }
+         if (ctx->opts.contention_factor.set) {
+            return _mongocrypt_ctx_fail_w_msg (
+               ctx, "cannot set both key alt name and contention factor");
+         }
+         if (ctx->opts.query_type.set) {
+            return _mongocrypt_ctx_fail_w_msg (
+               ctx, "cannot set both key alt name and query type");
+         }
+         if (ctx->opts.rangeopts.set) {
+            return _mongocrypt_ctx_fail_w_msg (
+               ctx, "cannot set both key alt name and range opts");
+         }
+      }
+      /* algorithm is FLE 1 only. */
+      if (ctx->opts.algorithm != MONGOCRYPT_ENCRYPTION_ALGORITHM_NONE) {
+         if (!_mongocrypt_buffer_empty (&ctx->opts.index_key_id)) {
+            return _mongocrypt_ctx_fail_w_msg (
+               ctx, "cannot set both algorithm and index key id");
+         }
+         if (ctx->opts.contention_factor.set) {
+            return _mongocrypt_ctx_fail_w_msg (
+               ctx, "cannot set both algorithm and contention factor");
+         }
+         if (ctx->opts.query_type.set) {
+            return _mongocrypt_ctx_fail_w_msg (
+               ctx, "cannot set both algorithm and query type");
+         }
+         if (ctx->opts.rangeopts.set) {
+            return _mongocrypt_ctx_fail_w_msg (
+               ctx, "cannot set both algorithm and range opts");
+         }
+      }
+   }
+
+   if (ctx->opts.algorithm == MONGOCRYPT_ENCRYPTION_ALGORITHM_NONE &&
+       !ctx->opts.index_type.set) {
+      return _mongocrypt_ctx_fail_w_msg (ctx,
+                                         "algorithm or index type required");
+   }
+
+   if (ctx->opts.contention_factor.set && ctx->opts.index_type.set &&
+       ctx->opts.index_type.value == MONGOCRYPT_INDEX_TYPE_NONE) {
+      return _mongocrypt_ctx_fail_w_msg (
+         ctx, "cannot set contention factor with no index type");
+   }
+
+   if (ctx->opts.query_type.set && ctx->opts.index_type.set &&
+       ctx->opts.index_type.value == MONGOCRYPT_INDEX_TYPE_NONE) {
+      return _mongocrypt_ctx_fail_w_msg (
+         ctx, "cannot set query type with no index type");
+   }
+
+   if (ctx->opts.rangeopts.set && ctx->opts.index_type.set) {
+      if (ctx->opts.index_type.value == MONGOCRYPT_INDEX_TYPE_NONE) {
+         return _mongocrypt_ctx_fail_w_msg (
+            ctx, "cannot set range opts with no index type");
+      }
+
+      if (ctx->opts.index_type.value == MONGOCRYPT_INDEX_TYPE_EQUALITY) {
+         return _mongocrypt_ctx_fail_w_msg (
+            ctx, "cannot set range opts with equality index type");
+      }
+   }
+
+   if (ctx->opts.contention_factor.set &&
+       !mc_validate_contention (ctx->opts.contention_factor.value,
+                                ctx->status)) {
+      return _mongocrypt_ctx_fail (ctx);
+   }
+
+   if (ctx->opts.index_type.set &&
+       ctx->opts.index_type.value == MONGOCRYPT_INDEX_TYPE_EQUALITY &&
+       !ctx->opts.contention_factor.set) {
+      return _mongocrypt_ctx_fail_w_msg (
+         ctx, "contention factor is required for indexed algorithm");
+   }
+
+   if (ctx->opts.index_type.set &&
+       ctx->opts.index_type.value == MONGOCRYPT_INDEX_TYPE_RANGEPREVIEW) {
+      if (!ctx->opts.contention_factor.set) {
+         return _mongocrypt_ctx_fail_w_msg (
+            ctx, "contention factor is required for range indexed algorithm");
+      }
+
+      if (!ctx->opts.rangeopts.set) {
+         return _mongocrypt_ctx_fail_w_msg (
+            ctx, "range opts are required for range indexed algorithm");
+      }
+   }
+
+   if (ctx->opts.rangeopts.set &&
+       !mc_validate_sparsity (ctx->opts.rangeopts.value.sparsity,
+                              ctx->status)) {
+      return _mongocrypt_ctx_fail (ctx);
+   }
+
+   // If query type is set, it must match the index type.
+   if (ctx->opts.query_type.set && ctx->opts.index_type.set) {
+      mongocrypt_status_t *const status = ctx->status;
+      bool matches = false;
+
+      switch (ctx->opts.query_type.value) {
+      case MONGOCRYPT_QUERY_TYPE_RANGEPREVIEW:
+         matches =
+            (ctx->opts.index_type.value == MONGOCRYPT_INDEX_TYPE_RANGEPREVIEW);
+         break;
+      case MONGOCRYPT_QUERY_TYPE_EQUALITY:
+         matches =
+            (ctx->opts.index_type.value == MONGOCRYPT_INDEX_TYPE_EQUALITY);
+         break;
+      default:
+         CLIENT_ERR ("unsupported value for query_type: %d",
+                     ctx->opts.query_type.value);
+         return _mongocrypt_ctx_fail (ctx);
+      }
+
+      if (!matches) {
+         CLIENT_ERR (
+            "query_type (%s) must match index_type (%s)",
+            _mongocrypt_query_type_to_string (ctx->opts.query_type.value),
+            _mongocrypt_index_type_to_string (ctx->opts.index_type.value));
+         return _mongocrypt_ctx_fail (ctx);
+      }
+   }
+
+   ectx = (_mongocrypt_ctx_encrypt_t *) ctx;
+   ctx->type = _MONGOCRYPT_TYPE_ENCRYPT;
+   ectx->explicit = true;
+   ctx->vtable.finalize = _finalize;
+   ctx->vtable.cleanup = _cleanup;
+
+   if (!msg || !msg->data) {
+      return _mongocrypt_ctx_fail_w_msg (
+         ctx, "msg required for explicit encryption");
+   }
+
+   if (ctx->opts.key_alt_names) {
+      if (!_mongocrypt_key_broker_request_name (
+             &ctx->kb, &ctx->opts.key_alt_names->value)) {
+         return _mongocrypt_ctx_fail (ctx);
+      }
+   } else {
+      if (!_mongocrypt_key_broker_request_id (&ctx->kb, &ctx->opts.key_id)) {
+         return _mongocrypt_ctx_fail (ctx);
+      }
+   }
+
+   if (!_mongocrypt_buffer_empty (&ctx->opts.index_key_id)) {
+      if (!_mongocrypt_key_broker_request_id (&ctx->kb,
+                                              &ctx->opts.index_key_id)) {
+         return _mongocrypt_ctx_fail (ctx);
+      }
+   }
+
+   _mongocrypt_buffer_init (&ectx->original_cmd);
+
+   _mongocrypt_buffer_copy_from_binary (&ectx->original_cmd, msg);
+   if (!_mongocrypt_buffer_to_bson (&ectx->original_cmd, &as_bson)) {
+      return _mongocrypt_ctx_fail_w_msg (ctx, "msg must be bson");
+   }
+
+   if (ctx->crypt->log.trace_enabled) {
+      char *cmd_val;
+      cmd_val = _mongocrypt_new_json_string_from_binary (msg);
+      _mongocrypt_log (&ctx->crypt->log,
+                       MONGOCRYPT_LOG_LEVEL_TRACE,
+                       "%s (%s=\"%s\")",
+                       BSON_FUNC,
+                       "msg",
+                       cmd_val);
+      bson_free (cmd_val);
+   }
+
+   if (!bson_iter_init_find (&iter, &as_bson, "v")) {
+      return _mongocrypt_ctx_fail_w_msg (ctx, "invalid msg, must contain 'v'");
+   }
+
+   if (!_permitted_for_encryption (&iter, ctx->opts.algorithm, ctx->status)) {
+      return _mongocrypt_ctx_fail (ctx);
+   }
+
+   (void) _mongocrypt_key_broker_requests_done (&ctx->kb);
+   return _mongocrypt_ctx_state_from_key_broker (ctx);
+}
+
+bool
+mongocrypt_ctx_explicit_encrypt_init (mongocrypt_ctx_t *ctx,
+                                      mongocrypt_binary_t *msg)
+{
+   if (!explicit_encrypt_init (ctx, msg)) {
+      return false;
+   }
+   if (ctx->opts.query_type.set &&
+       ctx->opts.query_type.value == MONGOCRYPT_QUERY_TYPE_RANGEPREVIEW) {
+      return _mongocrypt_ctx_fail_w_msg (
+         ctx,
+         "Encrypt may not be used for range queries. Use EncryptExpression.");
+   }
+   return true;
+}
+
+bool
+mongocrypt_ctx_explicit_encrypt_expression_init (mongocrypt_ctx_t *ctx,
+                                                 mongocrypt_binary_t *msg)
+{
+   if (!explicit_encrypt_init (ctx, msg)) {
+      return false;
+   }
+   if (!ctx->opts.query_type.set ||
+       ctx->opts.query_type.value != MONGOCRYPT_QUERY_TYPE_RANGEPREVIEW) {
+      return _mongocrypt_ctx_fail_w_msg (
+         ctx, "EncryptExpression may only be used for range queries.");
+   }
+   return true;
+}
+
+static bool
+_check_cmd_for_auto_encrypt (mongocrypt_binary_t *cmd,
+                             bool *bypass,
+                             char **collname,
+                             mongocrypt_status_t *status)
+{
+   bson_t as_bson;
+   bson_iter_t iter, ns_iter;
+   const char *cmd_name;
+   bool eligible = false;
+
+   BSON_ASSERT_PARAM (cmd);
+   BSON_ASSERT_PARAM (bypass);
+   BSON_ASSERT_PARAM (collname);
+
+   *bypass = false;
+
+   if (!_mongocrypt_binary_to_bson (cmd, &as_bson) ||
+       !bson_iter_init (&iter, &as_bson)) {
+      CLIENT_ERR ("invalid BSON");
+      return false;
+   }
+
+   /* The command name is the first key. */
+   if (!bson_iter_next (&iter)) {
+      CLIENT_ERR ("invalid empty BSON");
+      return false;
+   }
+
+   cmd_name = bson_iter_key (&iter);
+   BSON_ASSERT (cmd_name);
+
+   /* get the collection name (or NULL if database/client command). */
+   if (0 == strcmp (cmd_name, "explain")) {
+      if (!BSON_ITER_HOLDS_DOCUMENT (&iter)) {
+         CLIENT_ERR ("explain value is not a document");
+         return false;
+      }
+      if (!bson_iter_recurse (&iter, &ns_iter)) {
+         CLIENT_ERR ("malformed BSON for encrypt command");
+         return false;
+      }
+      if (!bson_iter_next (&ns_iter)) {
+         CLIENT_ERR ("invalid empty BSON");
+         return false;
+      }
+   } else {
+      memcpy (&ns_iter, &iter, sizeof (iter));
+   }
+
+   if (BSON_ITER_HOLDS_UTF8 (&ns_iter)) {
+      *collname = bson_strdup (bson_iter_utf8 (&ns_iter, NULL));
+   } else {
+      *collname = NULL;
+   }
+
+   /* check if command is eligible for auto encryption, bypassed, or ineligible.
+    */
+   if (0 == strcmp (cmd_name, "aggregate")) {
+      /* collection level aggregate ok, database/client is not. */
+      eligible = true;
+   } else if (0 == strcmp (cmd_name, "count")) {
+      eligible = true;
+   } else if (0 == strcmp (cmd_name, "distinct")) {
+      eligible = true;
+   } else if (0 == strcmp (cmd_name, "delete")) {
+      eligible = true;
+   } else if (0 == strcmp (cmd_name, "find")) {
+      eligible = true;
+   } else if (0 == strcmp (cmd_name, "findAndModify")) {
+      eligible = true;
+   } else if (0 == strcmp (cmd_name, "getMore")) {
+      *bypass = true;
+   } else if (0 == strcmp (cmd_name, "insert")) {
+      eligible = true;
+   } else if (0 == strcmp (cmd_name, "update")) {
+      eligible = true;
+   } else if (0 == strcmp (cmd_name, "authenticate")) {
+      *bypass = true;
+   } else if (0 == strcmp (cmd_name, "getnonce")) {
+      *bypass = true;
+   } else if (0 == strcmp (cmd_name, "logout")) {
+      *bypass = true;
+   } else if (0 == bson_strcasecmp (cmd_name, "isMaster")) {
+      /* use case insensitive compare for ismaster, since some drivers send
+       * "ismaster" and others send "isMaster" */
+      *bypass = true;
+   } else if (0 == strcmp (cmd_name, "abortTransaction")) {
+      *bypass = true;
+   } else if (0 == strcmp (cmd_name, "commitTransaction")) {
+      *bypass = true;
+   } else if (0 == strcmp (cmd_name, "endSessions")) {
+      *bypass = true;
+   } else if (0 == strcmp (cmd_name, "startSession")) {
+      *bypass = true;
+   } else if (0 == strcmp (cmd_name, "create")) {
+      eligible = true;
+   } else if (0 == strcmp (cmd_name, "createIndexes")) {
+      eligible = true;
+   } else if (0 == strcmp (cmd_name, "drop")) {
+      *bypass = true;
+   } else if (0 == strcmp (cmd_name, "dropDatabase")) {
+      *bypass = true;
+   } else if (0 == strcmp (cmd_name, "dropIndexes")) {
+      *bypass = true;
+   } else if (0 == strcmp (cmd_name, "killCursors")) {
+      *bypass = true;
+   } else if (0 == strcmp (cmd_name, "listCollections")) {
+      *bypass = true;
+   } else if (0 == strcmp (cmd_name, "listDatabases")) {
+      *bypass = true;
+   } else if (0 == strcmp (cmd_name, "listIndexes")) {
+      *bypass = true;
+   } else if (0 == strcmp (cmd_name, "renameCollection")) {
+      *bypass = true;
+   } else if (0 == strcmp (cmd_name, "explain")) {
+      eligible = true;
+   } else if (0 == strcmp (cmd_name, "ping")) {
+      *bypass = true;
+   } else if (0 == strcmp (cmd_name, "saslStart")) {
+      *bypass = true;
+   } else if (0 == strcmp (cmd_name, "saslContinue")) {
+      *bypass = true;
+   } else if (0 == strcmp (cmd_name, "killAllSessions")) {
+      *bypass = true;
+   } else if (0 == strcmp (cmd_name, "killSessions")) {
+      *bypass = true;
+   } else if (0 == strcmp (cmd_name, "killAllSessionsByPattern")) {
+      *bypass = true;
+   } else if (0 == strcmp (cmd_name, "refreshSessions")) {
+      *bypass = true;
+   } else if (0 == strcmp (cmd_name, "compactStructuredEncryptionData")) {
+      eligible = true;
+   } else if (0 == strcmp (cmd_name, "collMod")) {
+      eligible = true;
+   } else if (0 == strcmp (cmd_name, "hello")) {
+      *bypass = true;
+   } else if (0 == strcmp (cmd_name, "buildInfo")) {
+      *bypass = true;
+   } else if (0 == strcmp (cmd_name, "getCmdLineOpts")) {
+      *bypass = true;
+   } else if (0 == strcmp (cmd_name, "getLog")) {
+      *bypass = true;
+   }
+
+   /* database/client commands are ineligible. */
+   if (eligible) {
+      if (!*collname) {
+         CLIENT_ERR (
+            "non-collection command not supported for auto encryption: %s",
+            cmd_name);
+         return false;
+      }
+      if (0 == strlen (*collname)) {
+         CLIENT_ERR ("empty collection name on command: %s", cmd_name);
+         return false;
+      }
+   }
+
+   if (eligible || *bypass) {
+      return true;
+   }
+
+   CLIENT_ERR ("command not supported for auto encryption: %s", cmd_name);
+   return false;
+}
+
+static bool
+needs_ismaster_check (mongocrypt_ctx_t *ctx)
+{
+   _mongocrypt_ctx_encrypt_t *ectx = (_mongocrypt_ctx_encrypt_t *) ctx;
+
+   BSON_ASSERT_PARAM (ctx);
+
+   bool using_mongocryptd =
+      !ectx->bypass_query_analysis && !ctx->crypt->csfle.okay;
+   // The "create" and "createIndexes" command require an isMaster check when
+   // using mongocryptd. See MONGOCRYPT-429.
+   return using_mongocryptd && (0 == strcmp (ectx->cmd_name, "create") ||
+                                0 == strcmp (ectx->cmd_name, "createIndexes"));
+}
+
+bool
+mongocrypt_ctx_encrypt_init (mongocrypt_ctx_t *ctx,
+                             const char *db,
+                             int32_t db_len,
+                             mongocrypt_binary_t *cmd)
+{
+   _mongocrypt_ctx_encrypt_t *ectx;
+   _mongocrypt_ctx_opts_spec_t opts_spec;
+   bool bypass;
+
+   if (!ctx) {
+      return false;
+   }
+
+   if (!db) {
+      return _mongocrypt_ctx_fail_w_msg (ctx, "invalid db");
+   }
+
+   memset (&opts_spec, 0, sizeof (opts_spec));
+   opts_spec.schema = OPT_OPTIONAL;
+   if (!_mongocrypt_ctx_init (ctx, &opts_spec)) {
+      return false;
+   }
+
+   ectx = (_mongocrypt_ctx_encrypt_t *) ctx;
+   ctx->type = _MONGOCRYPT_TYPE_ENCRYPT;
+   ectx->explicit = false;
+   ctx->vtable.mongo_op_collinfo = _mongo_op_collinfo;
+   ctx->vtable.mongo_feed_collinfo = _mongo_feed_collinfo;
+   ctx->vtable.mongo_done_collinfo = _mongo_done_collinfo;
+   ctx->vtable.mongo_op_collinfo = _mongo_op_collinfo;
+   ctx->vtable.mongo_op_markings = _mongo_op_markings;
+   ctx->vtable.mongo_feed_markings = _mongo_feed_markings;
+   ctx->vtable.mongo_done_markings = _mongo_done_markings;
+   ctx->vtable.finalize = _finalize;
+   ctx->vtable.cleanup = _cleanup;
+   ctx->vtable.mongo_op_collinfo = _mongo_op_collinfo;
+   ctx->vtable.mongo_feed_collinfo = _mongo_feed_collinfo;
+   ctx->vtable.mongo_done_collinfo = _mongo_done_collinfo;
+   ectx->bypass_query_analysis = ctx->crypt->opts.bypass_query_analysis;
+
+
+   if (!cmd || !cmd->data) {
+      return _mongocrypt_ctx_fail_w_msg (ctx, "invalid command");
+   }
+
+   _mongocrypt_buffer_copy_from_binary (&ectx->original_cmd, cmd);
+
+   ectx->cmd_name = get_command_name (&ectx->original_cmd, ctx->status);
+   if (!ectx->cmd_name) {
+      return _mongocrypt_ctx_fail (ctx);
+   }
+
+   if (!_check_cmd_for_auto_encrypt (
+          cmd, &bypass, &ectx->coll_name, ctx->status)) {
+      return _mongocrypt_ctx_fail (ctx);
+   }
+
+   if (bypass) {
+      ctx->nothing_to_do = true;
+      ctx->state = MONGOCRYPT_CTX_READY;
+      return true;
+   }
+
+   /* if _check_cmd_for_auto_encrypt did not bypass or error, a collection name
+    * must have been set. */
+   if (!ectx->coll_name) {
+      return _mongocrypt_ctx_fail_w_msg (
+         ctx,
+         "unexpected error: did not bypass or error but no collection name");
+   }
+
+   if (!_mongocrypt_validate_and_copy_string (db, db_len, &ectx->db_name) ||
+       0 == strlen (ectx->db_name)) {
+      return _mongocrypt_ctx_fail_w_msg (ctx, "invalid db");
+   }
+
+   ectx->ns = bson_strdup_printf ("%s.%s", ectx->db_name, ectx->coll_name);
+
+   if (ctx->opts.kek.provider.aws.region || ctx->opts.kek.provider.aws.cmk) {
+      return _mongocrypt_ctx_fail_w_msg (
+         ctx, "aws masterkey options must not be set");
+   }
+
+   if (!_mongocrypt_buffer_empty (&ctx->opts.key_id)) {
+      return _mongocrypt_ctx_fail_w_msg (
+         ctx, "key_id must not be set for auto encryption");
+   }
+
+   if (ctx->opts.algorithm != MONGOCRYPT_ENCRYPTION_ALGORITHM_NONE) {
+      return _mongocrypt_ctx_fail_w_msg (
+         ctx, "algorithm must not be set for auto encryption");
+   }
+
+   if (ctx->crypt->log.trace_enabled) {
+      char *cmd_val;
+      cmd_val = _mongocrypt_new_json_string_from_binary (cmd);
+      _mongocrypt_log (&ctx->crypt->log,
+                       MONGOCRYPT_LOG_LEVEL_TRACE,
+                       "%s (%s=\"%s\", %s=%d, %s=\"%s\")",
+                       BSON_FUNC,
+                       "db",
+                       ectx->db_name,
+                       "db_len",
+                       db_len,
+                       "cmd",
+                       cmd_val);
+      bson_free (cmd_val);
+   }
+
+   /* The "create" and "createIndexes" command require sending an isMaster
+    * request to mongocryptd. */
+   if (needs_ismaster_check (ctx)) {
+      /* We are using mongocryptd. We need to ensure that mongocryptd
+       * maxWireVersion >= 17. */
+      ectx->ismaster.needed = true;
+      ctx->state = MONGOCRYPT_CTX_NEED_MONGO_MARKINGS;
+      return true;
+   }
+
+   return mongocrypt_ctx_encrypt_ismaster_done (ctx);
+}
+
+#define WIRE_VERSION_SERVER_6 17
+/* mongocrypt_ctx_encrypt_ismaster_done is called when:
+ * 1. The max wire version of mongocryptd is known.
+ * 2. The max wire version of mongocryptd is not required for the command.
+ */
+static bool
+mongocrypt_ctx_encrypt_ismaster_done (mongocrypt_ctx_t *ctx)
+{
+   _mongocrypt_ctx_encrypt_t *ectx = (_mongocrypt_ctx_encrypt_t *) ctx;
+
+   BSON_ASSERT_PARAM (ctx);
+
+   ectx->ismaster.needed = false;
+
+   /* The "create" and "createIndexes" command require bypassing on mongocryptd
+    * older than version 6.0. */
+   if (needs_ismaster_check (ctx)) {
+      if (ectx->ismaster.maxwireversion < WIRE_VERSION_SERVER_6) {
+         /* Bypass. */
+         ctx->nothing_to_do = true;
+         ctx->state = MONGOCRYPT_CTX_READY;
+         return true;
+      }
+   }
+
+   /* Check if there is an encrypted field config in encrypted_field_config_map
+    */
+   if (!_fle2_try_encrypted_field_config_from_map (ctx)) {
+      return false;
+   }
+   if (_mongocrypt_buffer_empty (&ectx->encrypted_field_config)) {
+      if (!_try_schema_from_create_or_collMod_cmd (ctx)) {
+         return false;
+      }
+
+      /* Check if we have a local schema from schema_map */
+      if (_mongocrypt_buffer_empty (&ectx->schema)) {
+         if (!_try_schema_from_schema_map (ctx)) {
+            return false;
+         }
+      }
+
+      /* If we didn't have a local schema, try the cache. */
+      if (_mongocrypt_buffer_empty (&ectx->schema)) {
+         if (!_try_schema_from_cache (ctx)) {
+            return false;
+         }
+      }
+
+      /* If we did not have a local or cached schema, check if this is a
+       * "create" command. If it is a "create" command, do not run
+       * "listCollections" to get a server-side schema. */
+      if (_mongocrypt_buffer_empty (&ectx->schema) &&
+          !_try_empty_schema_for_create (ctx)) {
+         return false;
+      }
+
+      /* Otherwise, we need the the driver to fetch the schema. */
+      if (_mongocrypt_buffer_empty (&ectx->schema)) {
+         ctx->state = MONGOCRYPT_CTX_NEED_MONGO_COLLINFO;
+      }
+   }
+
+   /* If an encrypted_field_config was set, check if keys are required for
+    * delete tokens. */
+   if (!_fle2_collect_keys_for_deleteTokens (ctx)) {
+      return false;
+   }
+
+   if (!_fle2_collect_keys_for_compact (ctx)) {
+      return false;
+   }
+
+   if (ctx->state == MONGOCRYPT_CTX_NEED_MONGO_MARKINGS) {
+      if (ectx->bypass_query_analysis) {
+         /* Keys may have been requested for deleteTokens or compactionTokens.
+          * Finish key requests.
+          */
+         _mongocrypt_key_broker_requests_done (&ctx->kb);
+         return _mongocrypt_ctx_state_from_key_broker (ctx);
+      }
+      // We're ready for markings. Try to generate them ourself.
+      return _try_run_csfle_marking (ctx);
+   } else {
+      // Other state, return to caller.
+      return true;
+   }
+}