Outlook Email Stuck in the Outbox? How to Fix It
You clicked Send ten minutes ago and the email is still sitting in the Outbox, sometimes in italics, refusing to go. Usually there's a simple reason — and sometimes you just need to get the thing out of there. Here's how.
Quick reference
| Likely cause | Fix |
|---|---|
| Attachment too big | Remove it; send a OneDrive link |
| Working Offline | Send/Receive → Work Offline to turn it off |
| Password needed | Click Need Password at the bottom |
| Scheduled send | It's waiting on purpose — check Delay Delivery |
| Just stuck | Open it from the Outbox and click Send again |
1. Try the simple things first
1. Press F9 (Send/Receive All Folders) in classic Outlook, or click Sync in new Outlook.
2. Check the bottom of the classic Outlook window: if it says Working Offline, click Send/Receive → Work Offline to reconnect. If it says Need Password, click it and sign in.
3. Check your internet connection by opening a web page.
2. Check the bottom of the classic Outlook window: if it says Working Offline, click Send/Receive → Work Offline to reconnect. If it says Need Password, click it and sign in.
3. Check your internet connection by opening a web page.
2. Is it meant to be waiting?
If you used Schedule send or Delay Delivery, the email sits in the Outbox (classic) or Drafts (new Outlook) until the time you chose. Open it and check Options → Delay Delivery (classic). Untick Do not deliver before to send it now.
Also check for a rule that defers delivery — some people set one up as an "undo send" safety net and forget.
3. Is the attachment too big?
The commonest cause. Most mail servers reject emails over about 20–25 MB, and Outlook keeps trying.
1. Open the Outbox folder.
2. Drag the email to Drafts (this stops Outlook trying to send it).
3. Open it from Drafts, remove the attachment, and attach the file as a OneDrive link instead (Attach → Browse cloud locations).
4. Send.
2. Drag the email to Drafts (this stops Outlook trying to send it).
3. Open it from Drafts, remove the attachment, and attach the file as a OneDrive link instead (Attach → Browse cloud locations).
4. Send.
4. Re-send a stuck email
Sometimes Outlook starts sending, gets interrupted, and the email is left half-done.
1. Open the Outbox.
2. Double-click the email to open it.
3. Click Send again.
2. Double-click the email to open it.
3. Click Send again.
If it won't open ("Outlook has already begun transmitting this message"), switch to Work Offline first, wait a few seconds, open the email, then switch back online and send.
5. Delete an email from the Outbox
Want it gone rather than sent?
1. Classic Outlook: click Send/Receive → Work Offline so Outlook stops trying.
2. Open the Outbox, right-click the email and choose Delete.
3. Turn Work Offline off again.
2. Open the Outbox, right-click the email and choose Delete.
3. Turn Work Offline off again.
In new Outlook, open the Outbox, select the email and press Delete.
6. Check your account settings
If every email gets stuck:
• Password changed? Classic: File → Account Settings → Account Settings → Repair. New Outlook: Settings → Accounts → Email accounts → Manage → Repair, or remove and re-add the account.
• Gmail, Yahoo or another provider? Check they haven't blocked the sign-in — look for a security email from them and approve the device.
• Antivirus scanning outgoing mail? Some antivirus "email protection" features hold up sending. Temporarily disable that feature (not the whole antivirus) to test.
• Gmail, Yahoo or another provider? Check they haven't blocked the sign-in — look for a security email from them and approve the device.
• Antivirus scanning outgoing mail? Some antivirus "email protection" features hold up sending. Temporarily disable that feature (not the whole antivirus) to test.
7. Last resort: Safe Mode and a new profile (classic Outlook)
Hold Ctrl while opening Outlook to start it in Safe Mode without add-ins. If sending works, an add-in is the problem — disable them via File → Options → Add-ins → Go. If it still fails, create a new mail profile via Control Panel → Mail → Show Profiles.
Troubleshooting
The email sent twice. Outlook sent it, lost the confirmation and tried again. Annoying but harmless — apologise and move on. It usually means a flaky connection.
The recipient got a blank or empty email. It was sent while Outlook was still uploading. Resend it.
The Outbox shows a number but is empty. A hidden or corrupt item. Switch Work Offline on, restart Outlook, then look again; if it persists, the ScanPST repair tool (search your PC for it) fixes the data file.
Wrapping up
Check Work Offline and Need Password, look for a delay, and remove any big attachment. If one email is simply stuck, drag it to Drafts and send it again.
