diff --git a/FlowCrypt/src/main/java/com/flowcrypt/email/api/email/model/OutgoingMessageInfo.kt b/FlowCrypt/src/main/java/com/flowcrypt/email/api/email/model/OutgoingMessageInfo.kt
index 6d3aa27d6..f42421d64 100644
--- a/FlowCrypt/src/main/java/com/flowcrypt/email/api/email/model/OutgoingMessageInfo.kt
+++ b/FlowCrypt/src/main/java/com/flowcrypt/email/api/email/model/OutgoingMessageInfo.kt
@@ -37,7 +37,7 @@ data class OutgoingMessageInfo(
   @Expose val encryptionType: MessageEncryptionType? = null,
   @Expose @MessageType val messageType: Int = MessageType.NEW,
   @Expose val replyToMessageEntityId: Long? = null,
-  @Expose val uid: Long = 0,
+  @Expose val uid: Long = System.currentTimeMillis(),
   @Expose val password: CharArray? = null,
   @Expose val timestamp: Long = System.currentTimeMillis(),
   @Expose val signature: String? = null,
diff --git a/FlowCrypt/src/main/java/com/flowcrypt/email/jetpack/viewmodel/CreateOutgoingMessageViewModel.kt b/FlowCrypt/src/main/java/com/flowcrypt/email/jetpack/viewmodel/CreateOutgoingMessageViewModel.kt
index b3db572fe..24318829e 100644
--- a/FlowCrypt/src/main/java/com/flowcrypt/email/jetpack/viewmodel/CreateOutgoingMessageViewModel.kt
+++ b/FlowCrypt/src/main/java/com/flowcrypt/email/jetpack/viewmodel/CreateOutgoingMessageViewModel.kt
@@ -85,14 +85,13 @@ class CreateOutgoingMessageViewModel(
         }
 
         val messageId = roomDatabase.msgDao().insertSuspend(messageEntity)
-        messageEntity = messageEntity.copy(id = messageId, uid = messageId)
+        messageEntity = messageEntity.copy(id = messageId, uid = outgoingMessageInfo.uid)
         roomDatabase.msgDao().updateSuspend(messageEntity)
 
         updateOutgoingMsgCount(activeAccount.email, activeAccount.accountType)
         ProcessingOutgoingMessageInfoHelper.process(
           context = context,
           originalOutgoingMessageInfo = outgoingMessageInfo.copy(
-            uid = messageId,
             atts = outgoingMessageInfo.atts?.map {
               it.copy(
                 email = outgoingMessageInfo.account,
diff --git a/FlowCrypt/src/main/java/com/flowcrypt/email/jetpack/viewmodel/DraftViewModel.kt b/FlowCrypt/src/main/java/com/flowcrypt/email/jetpack/viewmodel/DraftViewModel.kt
index 5016886cf..c1ab8d3eb 100644
--- a/FlowCrypt/src/main/java/com/flowcrypt/email/jetpack/viewmodel/DraftViewModel.kt
+++ b/FlowCrypt/src/main/java/com/flowcrypt/email/jetpack/viewmodel/DraftViewModel.kt
@@ -296,7 +296,7 @@ class DraftViewModel(
         account = accountEntity.email,
         accountType = accountEntity.accountType,
         label = folderDrafts.fullName,
-        uid = System.currentTimeMillis(),
+        uid = outgoingMessageInfo.uid,
         info = outgoingMessageInfo,
         flags = listOf(MessageFlag.DRAFT, MessageFlag.SEEN)
       ).copy(
@@ -319,6 +319,14 @@ class DraftViewModel(
           draftEntity.copy(state = MessageState.PENDING_DELETING_DRAFT.value)
         )
 
+        val draftsDir = CacheManager.getDraftDirectory(getApplication())
+
+        draftsDir.walkTopDown().firstOrNull {
+          it.name == draftEntity.id.toString()
+        }?.let { currentMsgDraftDir ->
+          FileAndDirectoryUtils.deleteDir(currentMsgDraftDir)
+        }
+
         DeleteDraftsWorker.enqueue(getApplication())
       }
     }
diff --git a/FlowCrypt/src/main/java/com/flowcrypt/email/jetpack/workmanager/sync/UploadDraftsWorker.kt b/FlowCrypt/src/main/java/com/flowcrypt/email/jetpack/workmanager/sync/UploadDraftsWorker.kt
index 76abf5d46..772e2b0a6 100644
--- a/FlowCrypt/src/main/java/com/flowcrypt/email/jetpack/workmanager/sync/UploadDraftsWorker.kt
+++ b/FlowCrypt/src/main/java/com/flowcrypt/email/jetpack/workmanager/sync/UploadDraftsWorker.kt
@@ -122,10 +122,22 @@ class UploadDraftsWorker(context: Context, params: WorkerParameters) :
       for (directory in directories) {
         val directoryName = directory.name
         val existingDraftEntity = roomDatabase.msgDao().getMsgById(directoryName.toLong())
+
         if (existingDraftEntity == null) {
           FileAndDirectoryUtils.deleteDir(directory)
           continue
         }
+
+        val activeAccount = roomDatabase.accountDao().getActiveAccountSuspend()
+        if (activeAccount != null) {
+          val outgoingMessages = roomDatabase.msgDao().getOutboxMsgsSuspend(activeAccount.email)
+          if (outgoingMessages.any { it.uid == existingDraftEntity.uid }) {
+            //it looks like a user sent a message for this draft
+            FileAndDirectoryUtils.deleteDir(directory)
+            continue
+          }
+        }
+
         val drafts = directory.listFiles(FileFilter { it.isFile }) ?: emptyArray()
         try {
           setProgress(