sent emails are stuck in outbox

Question

I have 4 Outlook accounts on my laptop (all are gmail accounts for different family members). Emails are sending and being received from 3 of these, but are not being received / stuck in outbox on the 4th account. I changed the google password on that account today - logged in to google using the new password and gmail works fine - but not Outlook.

I tried to delete the account in Outlook under 'File' so I could try re-installing, but I couldn't delete it

Answer 1

Hi Chester Kidd,

Welcome to Microsoft Q&A forum.

You may refer to the troubleshooting steps provided in the Q&A Assist reply, as they cover the most common reasons why messages remain queued in the Outbox in Classic Outlook.

In addition, since you’re using Classic Outlook, this may still be stuck due to old Gmail OAuth tokens / cached credentials after the password change. I recommend doing the following to force a fresh sign-in:

• On your Google Account: go to Security >Microsoft apps & services > Remove all access.
• On Windows: open Credential Manager > Windows Credentials, then remove entries named MicrosoftOffice16_Data:OAUTH2… tp_google_imap_Oauth2 (usually two entries per Gmail account). After that, reopen Outlook and complete the browser sign-in again.

Please feel free to let me know if you have any further updates, thanks.

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Answer 2

Use Outlook to isolate the stuck account and clear any blocked messages, then reconfigure the Gmail account if needed.

1. Check for stuck messages and connection
   1. In Outlook, select the problematic Gmail account’s Outbox folder.
   2. If any messages are listed there, they may be blocking send/receive (especially if they have large attachments).
   3. On the ribbon, select Send/Receive > Work Offline so Outlook stops trying to send.
   4. In Outbox:
      • Either delete the stuck message, or
      • Drag it to Drafts, open it, and remove any large attachment, then save.
   5. If Outlook says it is still transmitting the message and won’t let it be deleted, close Outlook. If it does not close, use Ctrl+Alt+Delete → Task Manager → Processes tab → select outlook.exe → End Process.
   6. Reopen Outlook, verify the Outbox for that account is empty or only contains corrected messages.
   7. Turn Send/Receive > Work Offline off again to reconnect, then try sending a test email from that Gmail account.
2. Confirm Outlook is actually online
   • In Send/Receive, check the Work Offline button. If it is highlighted (blue), Outlook is offline and will not send. Click it so it is not highlighted, then select Send All.
3. Ensure automatic sending is enabled
   1. Go to File > Options.
   2. Select Advanced.
   3. In the Send and receive section, make sure Send immediately when connected is enabled.
   4. Select OK, then test sending again from the affected Gmail account.
4. If the account still will not send
   • After clearing the Outbox and confirming Outlook is online and set to send immediately, re-add the Gmail account (if Outlook allows removal). If removal is blocked, first ensure there is at least one other default data file/profile so the problematic account is not the only/default data store, then try again.
   • Once removed, add the Gmail account back using the updated Google password.

Note: Editing the Windows registry is only for advanced scenarios and should be done with care, as incorrect changes can require reinstalling Windows.

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References:

• Outlook email stuck
• Outlook keeps trying to send a nonexistent message while Outbox folder shows zero messages