@askexenow/exe-os 0.9.52 → 0.9.54

package/dist/bin/backfill-conversations.js

@@ -3443,6 +3443,15 @@ function readMachineId() {
     return "";
   }
 }
+function encryptWithMachineKey(plaintext, machineKey) {
+  const crypto3 = __require("crypto");
+  const iv = crypto3.randomBytes(12);
+  const cipher = crypto3.createCipheriv("aes-256-gcm", machineKey, iv);
+  let encrypted = cipher.update(plaintext, "utf-8", "base64");
+  encrypted += cipher.final("base64");
+  const authTag = cipher.getAuthTag().toString("base64");
+  return `${ENCRYPTED_PREFIX}${iv.toString("base64")}:${authTag}:${encrypted}`;
+}
 function decryptWithMachineKey(encrypted, machineKey) {
   if (!encrypted.startsWith(ENCRYPTED_PREFIX)) return null;
   try {
@@ -3461,6 +3470,21 @@ function decryptWithMachineKey(encrypted, machineKey) {
     return null;
   }
 }
+async function writeMachineBoundFileFallback(b64) {
+  const dir = getKeyDir();
+  await mkdir3(dir, { recursive: true });
+  const keyPath = getKeyPath();
+  const machineKey = deriveMachineKey();
+  if (machineKey) {
+    const encrypted = encryptWithMachineKey(b64, machineKey);
+    await writeFile3(keyPath, encrypted + "\n", "utf-8");
+    await chmod2(keyPath, 384);
+    return "encrypted";
+  }
+  await writeFile3(keyPath, b64 + "\n", "utf-8");
+  await chmod2(keyPath, 384);
+  return "plaintext";
+}
 async function getMasterKey() {
   const nativeValue = macKeychainGet() ?? linuxSecretGet();
   if (nativeValue) {
@@ -3512,6 +3536,20 @@ async function getMasterKey() {
     const migrated = macKeychainSet(b64Value) || linuxSecretSet(b64Value);
     if (migrated) {
       process.stderr.write("[keychain] Migrated key from file to native keychain.\n");
+      try {
+        await unlink(keyPath);
+        process.stderr.write("[keychain] Removed legacy master.key file after native keychain migration.\n");
+      } catch {
+      }
+    } else if (!content.startsWith(ENCRYPTED_PREFIX)) {
+      const fallback = await writeMachineBoundFileFallback(b64Value);
+      if (fallback === "encrypted") {
+        process.stderr.write("[keychain] Upgraded legacy plaintext master.key to machine-bound encrypted fallback.\n");
+      } else {
+        process.stderr.write(
+          "[keychain] WARNING: Could not encrypt legacy master.key \u2014 plaintext fallback remains.\n"
+        );
+      }
     }
     return key;
   } catch (err) {

package/dist/bin/backfill-responses.js

@@ -3442,6 +3442,15 @@ function readMachineId() {
     return "";
   }
 }
+function encryptWithMachineKey(plaintext, machineKey) {
+  const crypto3 = __require("crypto");
+  const iv = crypto3.randomBytes(12);
+  const cipher = crypto3.createCipheriv("aes-256-gcm", machineKey, iv);
+  let encrypted = cipher.update(plaintext, "utf-8", "base64");
+  encrypted += cipher.final("base64");
+  const authTag = cipher.getAuthTag().toString("base64");
+  return `${ENCRYPTED_PREFIX}${iv.toString("base64")}:${authTag}:${encrypted}`;
+}
 function decryptWithMachineKey(encrypted, machineKey) {
   if (!encrypted.startsWith(ENCRYPTED_PREFIX)) return null;
   try {
@@ -3460,6 +3469,21 @@ function decryptWithMachineKey(encrypted, machineKey) {
     return null;
   }
 }
+async function writeMachineBoundFileFallback(b64) {
+  const dir = getKeyDir();
+  await mkdir3(dir, { recursive: true });
+  const keyPath = getKeyPath();
+  const machineKey = deriveMachineKey();
+  if (machineKey) {
+    const encrypted = encryptWithMachineKey(b64, machineKey);
+    await writeFile3(keyPath, encrypted + "\n", "utf-8");
+    await chmod2(keyPath, 384);
+    return "encrypted";
+  }
+  await writeFile3(keyPath, b64 + "\n", "utf-8");
+  await chmod2(keyPath, 384);
+  return "plaintext";
+}
 async function getMasterKey() {
   const nativeValue = macKeychainGet() ?? linuxSecretGet();
   if (nativeValue) {
@@ -3511,6 +3535,20 @@ async function getMasterKey() {
     const migrated = macKeychainSet(b64Value) || linuxSecretSet(b64Value);
     if (migrated) {
       process.stderr.write("[keychain] Migrated key from file to native keychain.\n");
+      try {
+        await unlink(keyPath);
+        process.stderr.write("[keychain] Removed legacy master.key file after native keychain migration.\n");
+      } catch {
+      }
+    } else if (!content.startsWith(ENCRYPTED_PREFIX)) {
+      const fallback = await writeMachineBoundFileFallback(b64Value);
+      if (fallback === "encrypted") {
+        process.stderr.write("[keychain] Upgraded legacy plaintext master.key to machine-bound encrypted fallback.\n");
+      } else {
+        process.stderr.write(
+          "[keychain] WARNING: Could not encrypt legacy master.key \u2014 plaintext fallback remains.\n"
+        );
+      }
     }
     return key;
   } catch (err) {

package/dist/bin/backfill-vectors.js

@@ -3430,6 +3430,15 @@ function readMachineId() {
     return "";
   }
 }
+function encryptWithMachineKey(plaintext, machineKey) {
+  const crypto2 = __require("crypto");
+  const iv = crypto2.randomBytes(12);
+  const cipher = crypto2.createCipheriv("aes-256-gcm", machineKey, iv);
+  let encrypted = cipher.update(plaintext, "utf-8", "base64");
+  encrypted += cipher.final("base64");
+  const authTag = cipher.getAuthTag().toString("base64");
+  return `${ENCRYPTED_PREFIX}${iv.toString("base64")}:${authTag}:${encrypted}`;
+}
 function decryptWithMachineKey(encrypted, machineKey) {
   if (!encrypted.startsWith(ENCRYPTED_PREFIX)) return null;
   try {
@@ -3448,6 +3457,21 @@ function decryptWithMachineKey(encrypted, machineKey) {
     return null;
   }
 }
+async function writeMachineBoundFileFallback(b64) {
+  const dir = getKeyDir();
+  await mkdir3(dir, { recursive: true });
+  const keyPath = getKeyPath();
+  const machineKey = deriveMachineKey();
+  if (machineKey) {
+    const encrypted = encryptWithMachineKey(b64, machineKey);
+    await writeFile3(keyPath, encrypted + "\n", "utf-8");
+    await chmod2(keyPath, 384);
+    return "encrypted";
+  }
+  await writeFile3(keyPath, b64 + "\n", "utf-8");
+  await chmod2(keyPath, 384);
+  return "plaintext";
+}
 async function getMasterKey() {
   const nativeValue = macKeychainGet() ?? linuxSecretGet();
   if (nativeValue) {
@@ -3499,6 +3523,20 @@ async function getMasterKey() {
     const migrated = macKeychainSet(b64Value) || linuxSecretSet(b64Value);
     if (migrated) {
       process.stderr.write("[keychain] Migrated key from file to native keychain.\n");
+      try {
+        await unlink(keyPath);
+        process.stderr.write("[keychain] Removed legacy master.key file after native keychain migration.\n");
+      } catch {
+      }
+    } else if (!content.startsWith(ENCRYPTED_PREFIX)) {
+      const fallback = await writeMachineBoundFileFallback(b64Value);
+      if (fallback === "encrypted") {
+        process.stderr.write("[keychain] Upgraded legacy plaintext master.key to machine-bound encrypted fallback.\n");
+      } else {
+        process.stderr.write(
+          "[keychain] WARNING: Could not encrypt legacy master.key \u2014 plaintext fallback remains.\n"
+        );
+      }
     }
     return key;
   } catch (err) {

package/dist/bin/cleanup-stale-review-tasks.js

@@ -2908,6 +2908,15 @@ function readMachineId() {
     return "";
   }
 }
+function encryptWithMachineKey(plaintext, machineKey) {
+  const crypto2 = __require("crypto");
+  const iv = crypto2.randomBytes(12);
+  const cipher = crypto2.createCipheriv("aes-256-gcm", machineKey, iv);
+  let encrypted = cipher.update(plaintext, "utf-8", "base64");
+  encrypted += cipher.final("base64");
+  const authTag = cipher.getAuthTag().toString("base64");
+  return `${ENCRYPTED_PREFIX}${iv.toString("base64")}:${authTag}:${encrypted}`;
+}
 function decryptWithMachineKey(encrypted, machineKey) {
   if (!encrypted.startsWith(ENCRYPTED_PREFIX)) return null;
   try {
@@ -2926,6 +2935,21 @@ function decryptWithMachineKey(encrypted, machineKey) {
     return null;
   }
 }
+async function writeMachineBoundFileFallback(b64) {
+  const dir = getKeyDir();
+  await mkdir3(dir, { recursive: true });
+  const keyPath = getKeyPath();
+  const machineKey = deriveMachineKey();
+  if (machineKey) {
+    const encrypted = encryptWithMachineKey(b64, machineKey);
+    await writeFile3(keyPath, encrypted + "\n", "utf-8");
+    await chmod2(keyPath, 384);
+    return "encrypted";
+  }
+  await writeFile3(keyPath, b64 + "\n", "utf-8");
+  await chmod2(keyPath, 384);
+  return "plaintext";
+}
 async function getMasterKey() {
   const nativeValue = macKeychainGet() ?? linuxSecretGet();
   if (nativeValue) {
@@ -2977,6 +3001,20 @@ async function getMasterKey() {
     const migrated = macKeychainSet(b64Value) || linuxSecretSet(b64Value);
     if (migrated) {
       process.stderr.write("[keychain] Migrated key from file to native keychain.\n");
+      try {
+        await unlink(keyPath);
+        process.stderr.write("[keychain] Removed legacy master.key file after native keychain migration.\n");
+      } catch {
+      }
+    } else if (!content.startsWith(ENCRYPTED_PREFIX)) {
+      const fallback = await writeMachineBoundFileFallback(b64Value);
+      if (fallback === "encrypted") {
+        process.stderr.write("[keychain] Upgraded legacy plaintext master.key to machine-bound encrypted fallback.\n");
+      } else {
+        process.stderr.write(
+          "[keychain] WARNING: Could not encrypt legacy master.key \u2014 plaintext fallback remains.\n"
+        );
+      }
     }
     return key;
   } catch (err) {

package/dist/bin/cli.js

@@ -1919,6 +1919,21 @@ function decryptWithMachineKey(encrypted, machineKey) {
     return null;
   }
 }
+async function writeMachineBoundFileFallback(b64) {
+  const dir = getKeyDir();
+  await mkdir4(dir, { recursive: true });
+  const keyPath = getKeyPath();
+  const machineKey = deriveMachineKey();
+  if (machineKey) {
+    const encrypted = encryptWithMachineKey(b64, machineKey);
+    await writeFile4(keyPath, encrypted + "\n", "utf-8");
+    await chmod2(keyPath, 384);
+    return "encrypted";
+  }
+  await writeFile4(keyPath, b64 + "\n", "utf-8");
+  await chmod2(keyPath, 384);
+  return "plaintext";
+}
 async function getMasterKey() {
   const nativeValue = macKeychainGet() ?? linuxSecretGet();
   if (nativeValue) {
@@ -1970,6 +1985,20 @@ async function getMasterKey() {
     const migrated = macKeychainSet(b64Value) || linuxSecretSet(b64Value);
     if (migrated) {
       process.stderr.write("[keychain] Migrated key from file to native keychain.\n");
+      try {
+        await unlink(keyPath);
+        process.stderr.write("[keychain] Removed legacy master.key file after native keychain migration.\n");
+      } catch {
+      }
+    } else if (!content.startsWith(ENCRYPTED_PREFIX)) {
+      const fallback = await writeMachineBoundFileFallback(b64Value);
+      if (fallback === "encrypted") {
+        process.stderr.write("[keychain] Upgraded legacy plaintext master.key to machine-bound encrypted fallback.\n");
+      } else {
+        process.stderr.write(
+          "[keychain] WARNING: Could not encrypt legacy master.key \u2014 plaintext fallback remains.\n"
+        );
+      }
     }
     return key;
   } catch (err) {
@@ -1993,18 +2022,10 @@ async function setMasterKey(key) {
     } catch {
     }
   }
-  const dir = getKeyDir();
-  await mkdir4(dir, { recursive: true });
-  const keyPath = getKeyPath();
-  const machineKey = deriveMachineKey();
-  if (machineKey) {
-    const encrypted = encryptWithMachineKey(b64, machineKey);
-    await writeFile4(keyPath, encrypted + "\n", "utf-8");
-    await chmod2(keyPath, 384);
+  const fallback = await writeMachineBoundFileFallback(b64);
+  if (fallback === "encrypted") {
     process.stderr.write("[keychain] Key stored encrypted (machine-bound).\n");
   } else {
-    await writeFile4(keyPath, b64 + "\n", "utf-8");
-    await chmod2(keyPath, 384);
     process.stderr.write(
       "[keychain] WARNING: Key stored in plaintext file \u2014 no OS keychain available.\n"
     );
@@ -14458,6 +14479,31 @@ Audit method:
 6. Write structured report with PASS/FAIL per item
 
 After an audit, fix the findings yourself if you can. Don't hand off when you have the context.`
+      },
+      teddy: {
+        name: "teddy",
+        role: "Chief of Staff",
+        systemPrompt: `You are teddy, the Chief of Staff and executive assistant. You help the founder recall context, understand what happened, prepare concise briefs, and triage inbound conversations. You report to the COO.
+
+Your job is read-first, not action-first:
+- Retrieve memories, decisions, runbooks, and session context on demand
+- Summarize what matters without changing source data
+- Triage inbound conversations and surface likely bugs, requests, and follow-ups
+- Prepare daily briefs and "what changed?" summaries
+- Route recommended actions to the COO instead of taking them yourself
+
+Permissions boundary:
+- You are read-only by default.
+- You may use recall_my_memory, ask_team_memory, get_memory_by_id, get_session_context, search_everything, query_conversations, list_tasks, and get_task.
+- You must not create tasks, update tasks, store memories, send WhatsApp messages, mutate CRM/wiki/documents, deploy, or change configuration unless the founder explicitly promotes your permissions.
+- If a requested action requires write access, explain the action and recommend that the COO dispatch it.
+
+Operating style:
+- Be concise and precise.
+- Cite memory IDs, task IDs, timestamps, and sender names when available.
+- Distinguish fact from inference.
+- Never auto-message people. Never respond in group chats unless explicitly allowed by gateway permissions.
+- Preserve data sovereignty: do not export or forward private memory unless the founder explicitly asks.`
       }
     };
     CLIENT_COO_TEMPLATE = `---

package/dist/bin/exe-assign.js

@@ -3590,6 +3590,15 @@ function readMachineId() {
     return "";
   }
 }
+function encryptWithMachineKey(plaintext, machineKey) {
+  const crypto2 = __require("crypto");
+  const iv = crypto2.randomBytes(12);
+  const cipher = crypto2.createCipheriv("aes-256-gcm", machineKey, iv);
+  let encrypted = cipher.update(plaintext, "utf-8", "base64");
+  encrypted += cipher.final("base64");
+  const authTag = cipher.getAuthTag().toString("base64");
+  return `${ENCRYPTED_PREFIX}${iv.toString("base64")}:${authTag}:${encrypted}`;
+}
 function decryptWithMachineKey(encrypted, machineKey) {
   if (!encrypted.startsWith(ENCRYPTED_PREFIX)) return null;
   try {
@@ -3608,6 +3617,21 @@ function decryptWithMachineKey(encrypted, machineKey) {
     return null;
   }
 }
+async function writeMachineBoundFileFallback(b64) {
+  const dir = getKeyDir();
+  await mkdir3(dir, { recursive: true });
+  const keyPath = getKeyPath();
+  const machineKey = deriveMachineKey();
+  if (machineKey) {
+    const encrypted = encryptWithMachineKey(b64, machineKey);
+    await writeFile3(keyPath, encrypted + "\n", "utf-8");
+    await chmod2(keyPath, 384);
+    return "encrypted";
+  }
+  await writeFile3(keyPath, b64 + "\n", "utf-8");
+  await chmod2(keyPath, 384);
+  return "plaintext";
+}
 async function getMasterKey() {
   const nativeValue = macKeychainGet() ?? linuxSecretGet();
   if (nativeValue) {
@@ -3659,6 +3683,20 @@ async function getMasterKey() {
     const migrated = macKeychainSet(b64Value) || linuxSecretSet(b64Value);
     if (migrated) {
       process.stderr.write("[keychain] Migrated key from file to native keychain.\n");
+      try {
+        await unlink(keyPath);
+        process.stderr.write("[keychain] Removed legacy master.key file after native keychain migration.\n");
+      } catch {
+      }
+    } else if (!content.startsWith(ENCRYPTED_PREFIX)) {
+      const fallback = await writeMachineBoundFileFallback(b64Value);
+      if (fallback === "encrypted") {
+        process.stderr.write("[keychain] Upgraded legacy plaintext master.key to machine-bound encrypted fallback.\n");
+      } else {
+        process.stderr.write(
+          "[keychain] WARNING: Could not encrypt legacy master.key \u2014 plaintext fallback remains.\n"
+        );
+      }
     }
     return key;
   } catch (err) {

package/dist/bin/exe-boot.js

@@ -3288,6 +3288,21 @@ function decryptWithMachineKey(encrypted, machineKey) {
     return null;
   }
 }
+async function writeMachineBoundFileFallback(b64) {
+  const dir = getKeyDir();
+  await mkdir3(dir, { recursive: true });
+  const keyPath = getKeyPath();
+  const machineKey = deriveMachineKey();
+  if (machineKey) {
+    const encrypted = encryptWithMachineKey(b64, machineKey);
+    await writeFile3(keyPath, encrypted + "\n", "utf-8");
+    await chmod2(keyPath, 384);
+    return "encrypted";
+  }
+  await writeFile3(keyPath, b64 + "\n", "utf-8");
+  await chmod2(keyPath, 384);
+  return "plaintext";
+}
 async function getMasterKey() {
   const nativeValue = macKeychainGet() ?? linuxSecretGet();
   if (nativeValue) {
@@ -3339,6 +3354,20 @@ async function getMasterKey() {
     const migrated = macKeychainSet(b64Value) || linuxSecretSet(b64Value);
     if (migrated) {
       process.stderr.write("[keychain] Migrated key from file to native keychain.\n");
+      try {
+        await unlink(keyPath);
+        process.stderr.write("[keychain] Removed legacy master.key file after native keychain migration.\n");
+      } catch {
+      }
+    } else if (!content.startsWith(ENCRYPTED_PREFIX)) {
+      const fallback = await writeMachineBoundFileFallback(b64Value);
+      if (fallback === "encrypted") {
+        process.stderr.write("[keychain] Upgraded legacy plaintext master.key to machine-bound encrypted fallback.\n");
+      } else {
+        process.stderr.write(
+          "[keychain] WARNING: Could not encrypt legacy master.key \u2014 plaintext fallback remains.\n"
+        );
+      }
     }
     return key;
   } catch (err) {
@@ -3362,18 +3391,10 @@ async function setMasterKey(key) {
     } catch {
     }
   }
-  const dir = getKeyDir();
-  await mkdir3(dir, { recursive: true });
-  const keyPath = getKeyPath();
-  const machineKey = deriveMachineKey();
-  if (machineKey) {
-    const encrypted = encryptWithMachineKey(b64, machineKey);
-    await writeFile3(keyPath, encrypted + "\n", "utf-8");
-    await chmod2(keyPath, 384);
+  const fallback = await writeMachineBoundFileFallback(b64);
+  if (fallback === "encrypted") {
     process.stderr.write("[keychain] Key stored encrypted (machine-bound).\n");
   } else {
-    await writeFile3(keyPath, b64 + "\n", "utf-8");
-    await chmod2(keyPath, 384);
     process.stderr.write(
       "[keychain] WARNING: Key stored in plaintext file \u2014 no OS keychain available.\n"
     );

package/dist/bin/exe-call.js

@@ -950,6 +950,31 @@ Audit method:
 6. Write structured report with PASS/FAIL per item
 
 After an audit, fix the findings yourself if you can. Don't hand off when you have the context.`
+      },
+      teddy: {
+        name: "teddy",
+        role: "Chief of Staff",
+        systemPrompt: `You are teddy, the Chief of Staff and executive assistant. You help the founder recall context, understand what happened, prepare concise briefs, and triage inbound conversations. You report to the COO.
+
+Your job is read-first, not action-first:
+- Retrieve memories, decisions, runbooks, and session context on demand
+- Summarize what matters without changing source data
+- Triage inbound conversations and surface likely bugs, requests, and follow-ups
+- Prepare daily briefs and "what changed?" summaries
+- Route recommended actions to the COO instead of taking them yourself
+
+Permissions boundary:
+- You are read-only by default.
+- You may use recall_my_memory, ask_team_memory, get_memory_by_id, get_session_context, search_everything, query_conversations, list_tasks, and get_task.
+- You must not create tasks, update tasks, store memories, send WhatsApp messages, mutate CRM/wiki/documents, deploy, or change configuration unless the founder explicitly promotes your permissions.
+- If a requested action requires write access, explain the action and recommend that the COO dispatch it.
+
+Operating style:
+- Be concise and precise.
+- Cite memory IDs, task IDs, timestamps, and sender names when available.
+- Distinguish fact from inference.
+- Never auto-message people. Never respond in group chats unless explicitly allowed by gateway permissions.
+- Preserve data sovereignty: do not export or forward private memory unless the founder explicitly asks.`
       }
     };
     CLIENT_COO_TEMPLATE = `---

package/dist/bin/exe-cloud.js

@@ -138,6 +138,21 @@ function decryptWithMachineKey(encrypted, machineKey) {
     return null;
   }
 }
+async function writeMachineBoundFileFallback(b64) {
+  const dir = getKeyDir();
+  await mkdir(dir, { recursive: true });
+  const keyPath = getKeyPath();
+  const machineKey = deriveMachineKey();
+  if (machineKey) {
+    const encrypted = encryptWithMachineKey(b64, machineKey);
+    await writeFile(keyPath, encrypted + "\n", "utf-8");
+    await chmod(keyPath, 384);
+    return "encrypted";
+  }
+  await writeFile(keyPath, b64 + "\n", "utf-8");
+  await chmod(keyPath, 384);
+  return "plaintext";
+}
 async function getMasterKey() {
   const nativeValue = macKeychainGet() ?? linuxSecretGet();
   if (nativeValue) {
@@ -189,6 +204,20 @@ async function getMasterKey() {
     const migrated = macKeychainSet(b64Value) || linuxSecretSet(b64Value);
     if (migrated) {
       process.stderr.write("[keychain] Migrated key from file to native keychain.\n");
+      try {
+        await unlink(keyPath);
+        process.stderr.write("[keychain] Removed legacy master.key file after native keychain migration.\n");
+      } catch {
+      }
+    } else if (!content.startsWith(ENCRYPTED_PREFIX)) {
+      const fallback = await writeMachineBoundFileFallback(b64Value);
+      if (fallback === "encrypted") {
+        process.stderr.write("[keychain] Upgraded legacy plaintext master.key to machine-bound encrypted fallback.\n");
+      } else {
+        process.stderr.write(
+          "[keychain] WARNING: Could not encrypt legacy master.key \u2014 plaintext fallback remains.\n"
+        );
+      }
     }
     return key;
   } catch (err) {
@@ -212,18 +241,10 @@ async function setMasterKey(key) {
     } catch {
     }
   }
-  const dir = getKeyDir();
-  await mkdir(dir, { recursive: true });
-  const keyPath = getKeyPath();
-  const machineKey = deriveMachineKey();
-  if (machineKey) {
-    const encrypted = encryptWithMachineKey(b64, machineKey);
-    await writeFile(keyPath, encrypted + "\n", "utf-8");
-    await chmod(keyPath, 384);
+  const fallback = await writeMachineBoundFileFallback(b64);
+  if (fallback === "encrypted") {
     process.stderr.write("[keychain] Key stored encrypted (machine-bound).\n");
   } else {
-    await writeFile(keyPath, b64 + "\n", "utf-8");
-    await chmod(keyPath, 384);
     process.stderr.write(
       "[keychain] WARNING: Key stored in plaintext file \u2014 no OS keychain available.\n"
     );

package/dist/bin/exe-dispatch.js

@@ -6636,6 +6636,15 @@ function readMachineId() {
     return "";
   }
 }
+function encryptWithMachineKey(plaintext, machineKey) {
+  const crypto7 = __require("crypto");
+  const iv = crypto7.randomBytes(12);
+  const cipher = crypto7.createCipheriv("aes-256-gcm", machineKey, iv);
+  let encrypted = cipher.update(plaintext, "utf-8", "base64");
+  encrypted += cipher.final("base64");
+  const authTag = cipher.getAuthTag().toString("base64");
+  return `${ENCRYPTED_PREFIX}${iv.toString("base64")}:${authTag}:${encrypted}`;
+}
 function decryptWithMachineKey(encrypted, machineKey) {
   if (!encrypted.startsWith(ENCRYPTED_PREFIX)) return null;
   try {
@@ -6654,6 +6663,21 @@ function decryptWithMachineKey(encrypted, machineKey) {
     return null;
   }
 }
+async function writeMachineBoundFileFallback(b64) {
+  const dir = getKeyDir();
+  await mkdir4(dir, { recursive: true });
+  const keyPath = getKeyPath();
+  const machineKey = deriveMachineKey();
+  if (machineKey) {
+    const encrypted = encryptWithMachineKey(b64, machineKey);
+    await writeFile5(keyPath, encrypted + "\n", "utf-8");
+    await chmod2(keyPath, 384);
+    return "encrypted";
+  }
+  await writeFile5(keyPath, b64 + "\n", "utf-8");
+  await chmod2(keyPath, 384);
+  return "plaintext";
+}
 async function getMasterKey() {
   const nativeValue = macKeychainGet() ?? linuxSecretGet();
   if (nativeValue) {
@@ -6705,6 +6729,20 @@ async function getMasterKey() {
     const migrated = macKeychainSet(b64Value) || linuxSecretSet(b64Value);
     if (migrated) {
       process.stderr.write("[keychain] Migrated key from file to native keychain.\n");
+      try {
+        await unlink(keyPath);
+        process.stderr.write("[keychain] Removed legacy master.key file after native keychain migration.\n");
+      } catch {
+      }
+    } else if (!content.startsWith(ENCRYPTED_PREFIX)) {
+      const fallback = await writeMachineBoundFileFallback(b64Value);
+      if (fallback === "encrypted") {
+        process.stderr.write("[keychain] Upgraded legacy plaintext master.key to machine-bound encrypted fallback.\n");
+      } else {
+        process.stderr.write(
+          "[keychain] WARNING: Could not encrypt legacy master.key \u2014 plaintext fallback remains.\n"
+        );
+      }
     }
     return key;
   } catch (err) {

package/dist/bin/exe-doctor.js

@@ -3510,6 +3510,15 @@ function readMachineId() {
     return "";
   }
 }
+function encryptWithMachineKey(plaintext, machineKey) {
+  const crypto2 = __require("crypto");
+  const iv = crypto2.randomBytes(12);
+  const cipher = crypto2.createCipheriv("aes-256-gcm", machineKey, iv);
+  let encrypted = cipher.update(plaintext, "utf-8", "base64");
+  encrypted += cipher.final("base64");
+  const authTag = cipher.getAuthTag().toString("base64");
+  return `${ENCRYPTED_PREFIX}${iv.toString("base64")}:${authTag}:${encrypted}`;
+}
 function decryptWithMachineKey(encrypted, machineKey) {
   if (!encrypted.startsWith(ENCRYPTED_PREFIX)) return null;
   try {
@@ -3528,6 +3537,21 @@ function decryptWithMachineKey(encrypted, machineKey) {
     return null;
   }
 }
+async function writeMachineBoundFileFallback(b64) {
+  const dir = getKeyDir();
+  await mkdir3(dir, { recursive: true });
+  const keyPath = getKeyPath();
+  const machineKey = deriveMachineKey();
+  if (machineKey) {
+    const encrypted = encryptWithMachineKey(b64, machineKey);
+    await writeFile3(keyPath, encrypted + "\n", "utf-8");
+    await chmod2(keyPath, 384);
+    return "encrypted";
+  }
+  await writeFile3(keyPath, b64 + "\n", "utf-8");
+  await chmod2(keyPath, 384);
+  return "plaintext";
+}
 async function getMasterKey() {
   const nativeValue = macKeychainGet() ?? linuxSecretGet();
   if (nativeValue) {
@@ -3579,6 +3603,20 @@ async function getMasterKey() {
     const migrated = macKeychainSet(b64Value) || linuxSecretSet(b64Value);
     if (migrated) {
       process.stderr.write("[keychain] Migrated key from file to native keychain.\n");
+      try {
+        await unlink(keyPath);
+        process.stderr.write("[keychain] Removed legacy master.key file after native keychain migration.\n");
+      } catch {
+      }
+    } else if (!content.startsWith(ENCRYPTED_PREFIX)) {
+      const fallback = await writeMachineBoundFileFallback(b64Value);
+      if (fallback === "encrypted") {
+        process.stderr.write("[keychain] Upgraded legacy plaintext master.key to machine-bound encrypted fallback.\n");
+      } else {
+        process.stderr.write(
+          "[keychain] WARNING: Could not encrypt legacy master.key \u2014 plaintext fallback remains.\n"
+        );
+      }
     }
     return key;
   } catch (err) {