diff --git a/app/plugins/builtins/mail/routes.py b/app/plugins/builtins/mail/routes.py
index d069931..59b86a9 100644
--- a/app/plugins/builtins/mail/routes.py
+++ b/app/plugins/builtins/mail/routes.py
@@ -647,14 +647,17 @@ async def empty_folder(
     for mail in mails:
         if is_trash or not trash_folder:
             # Permanent delete from DB + IMAP EXPUNGE
-            await db.delete(mail)
+            # IMPORTANT: Call imap_delete_mail BEFORE db.delete, because imap_delete_mail
+            # reads the mail from DB to find its folder and imap_uid.
             try:
                 await mail_services.imap_delete_mail(db, mail.id, tenant_id, permanent=True)
+                await db.delete(mail)
             except Exception as exc:
                 import logging
                 logging.getLogger(__name__).warning(
                     "empty_folder: IMAP permanent delete failed for mail %s: %s, queuing for retry", mail.id, exc
                 )
+                await db.delete(mail)
                 queue_entry = MailSyncQueue(
                     tenant_id=tenant_id,
                     mail_id=mail.id,
@@ -666,14 +669,17 @@ async def empty_folder(
                 db.add(queue_entry)
         else:
             # Move to Trash folder (standard mail program logic)
-            mail.folder_id = trash_folder.id
+            # IMPORTANT: Call imap_delete_mail BEFORE changing folder_id,
+            # because imap_delete_mail reads mail.folder_id to find the IMAP folder.
             try:
                 await mail_services.imap_delete_mail(db, mail.id, tenant_id, permanent=False)
+                mail.folder_id = trash_folder.id
             except Exception as exc:
                 import logging
                 logging.getLogger(__name__).warning(
                     "empty_folder: IMAP move to Trash failed for mail %s: %s, queuing for retry", mail.id, exc
                 )
+                mail.folder_id = trash_folder.id
                 queue_entry = MailSyncQueue(
                     tenant_id=tenant_id,
                     mail_id=mail.id,
@@ -1627,13 +1633,17 @@ async def delete_mail(
 
     if trash_folder and mail.folder_id == trash_folder.id:
         # Mail is already in Trash → permanent delete from DB + IMAP EXPUNGE
-        await db.delete(mail)
-        await db.flush()
+        # IMPORTANT: Call imap_delete_mail BEFORE db.delete, because imap_delete_mail
+        # reads the mail from DB to find its folder and imap_uid.
         try:
             await mail_services.imap_delete_mail(db, m_id, tenant_id, permanent=True)
+            await db.delete(mail)
+            await db.flush()
         except Exception as exc:
             import logging
             logging.getLogger(__name__).warning("IMAP permanent delete failed for mail %s: %s, queuing for retry", m_id, exc)
+            await db.delete(mail)
+            await db.flush()
             queue_entry = MailSyncQueue(
                 tenant_id=tenant_id,
                 mail_id=m_id,
@@ -1646,13 +1656,17 @@ async def delete_mail(
             await db.flush()
     elif trash_folder:
         # Mail is NOT in Trash → move to Trash folder (standard mail program logic)
-        mail.folder_id = trash_folder.id
-        await db.flush()
+        # IMPORTANT: Call imap_delete_mail BEFORE changing folder_id,
+        # because imap_delete_mail reads mail.folder_id to find the IMAP folder.
         try:
             await mail_services.imap_delete_mail(db, m_id, tenant_id, permanent=False)
+            mail.folder_id = trash_folder.id
+            await db.flush()
         except Exception as exc:
             import logging
             logging.getLogger(__name__).warning("IMAP move to Trash failed for mail %s: %s, queuing for retry", m_id, exc)
+            mail.folder_id = trash_folder.id
+            await db.flush()
             queue_entry = MailSyncQueue(
                 tenant_id=tenant_id,
                 mail_id=m_id,
@@ -1665,13 +1679,17 @@ async def delete_mail(
             await db.flush()
     else:
         # No Trash folder found → permanent delete from DB + IMAP EXPUNGE
-        await db.delete(mail)
-        await db.flush()
+        # IMPORTANT: Call imap_delete_mail BEFORE db.delete, because imap_delete_mail
+        # reads the mail from DB to find its folder and imap_uid.
         try:
             await mail_services.imap_delete_mail(db, m_id, tenant_id, permanent=True)
+            await db.delete(mail)
+            await db.flush()
         except Exception as exc:
             import logging
             logging.getLogger(__name__).warning("IMAP delete failed for mail %s: %s, queuing for retry", m_id, exc)
+            await db.delete(mail)
+            await db.flush()
             queue_entry = MailSyncQueue(
                 tenant_id=tenant_id,
                 mail_id=m_id,