core: add logs to diagnose why decryption fails after changing password (#10139)

packages/core/src/api/sync/index.ts

@@ -387,6 +387,10 @@ export class Sync {
       const itemsToDecrypt = itemsByKeyVersion.get(keyInfo.version);
       if (!itemsToDecrypt || itemsToDecrypt.length === 0) continue;
 
+      this.logger.info("Decrypting using key", {
+        keyInfo: keyInfo.version,
+        items: itemsToDecrypt.length
+      });
       decrypted.push(
         ...(await this.db.storage().decryptMulti(keyInfo.key, itemsToDecrypt))
       );

packages/core/src/api/user-manager.ts

@@ -404,11 +404,13 @@ class UserManager {
     { version: KeyVersion; key: SerializedKey }[] | undefined
   > {
     const masterKey = await this.getMasterKey();
+    logger.info("master key exists: ", { masterKey: !!masterKey });
     if (!masterKey) return;
 
     const dataEncryptionKey = await this.keyManager.get("dataEncryptionKey", {
       refetchUser: false
     });
+    logger.info("DEK exists: ", { dataEncryptionKey: !!dataEncryptionKey });
     if (!dataEncryptionKey)
       return [
         {
@@ -424,6 +426,9 @@ class UserManager {
         refetchUser: false
       }
     );
+    logger.info("legacy DEK exists: ", {
+      legacyDataEncryptionKey: !!legacyDataEncryptionKey
+    });
     if (legacyDataEncryptionKey)
       keys.push({
         key: await this.keyManager.unwrapKey(
@@ -436,6 +441,10 @@ class UserManager {
       key: await this.keyManager.unwrapKey(dataEncryptionKey, masterKey),
       version: KEY_VERSION.DEK
     });
+    logger.info("Keys:", {
+      keys: keys.length,
+      keyVersions: keys.map((k) => k.version)
+    });
     return keys;
   }