When an email lands in the Outbox instead of Sent, it means something prevented it from being delivered. Outlook and some other clients will keep retrying, but often the fix is manual.

Why Emails Get Stuck

  • Your internet connection dropped at the moment of sending
  • The email has a very large attachment that exceeds your provider's size limit
  • Outlook is set to Work Offline
  • The SMTP server settings are incorrect or the server is temporarily down
  • An antivirus program is scanning outgoing mail and stalling the process

Fixing a Stuck Email in Outlook (Desktop)

  1. Check the status bar at the bottom of Outlook. If it says Working Offline, go to Send/Receive > Work Offline to toggle it off.
  2. Click the Outbox folder in the left pane. You should see the stuck message.
  3. Do not double-click to open it yet — opening it while Outlook is trying to send can cause errors. Instead, right-click the message and choose Move to Drafts first.
  4. Once it is safely in Drafts, open it, make any changes needed (reduce attachment size if it is very large), and click Send again.
  5. Press F9 or go to Send/Receive > Send All to trigger an immediate send attempt.

Fixing a Stuck Email in Gmail

Gmail's web interface rarely gets stuck, but the mobile app can. If an email shows as queued in the Gmail app, check your internet connection. Open the Outbox label (tap the menu icon > Outbox), then open the message and tap Send again. Alternatively, move it back to Drafts and resend.

Fixing a Stuck Email in Apple Mail

On a Mac, go to the Outbox mailbox in Mail's sidebar. Right-click the message and choose Move to Drafts. Check your SMTP settings under Mail > Settings > Accounts > Server Settings, then resend from Drafts.

If the email keeps getting stuck, it is worth checking whether your attachment is too large. Gmail has a 25 MB limit; Outlook.com and Yahoo are similar. Use a file-sharing link instead of attaching very large files.