My emails are stuck in the Outbox
Almost always either offline mode, a big attachment, or a flaky internet connection.
- Make sure you’re online — the bottom-right of Outlook should not say “Working Offline”. If it does, click Send/Receive → Work Offline to toggle it off.
- Click Send/Receive tab → Send All.
- Open the stuck email. If the attachment is over 25 MB, it will not send via Outlook — share it via OneDrive instead.
- Check it isn’t waiting on encryption (a lock icon) — the recipient’s tenant may not support it.
- Restart Outlook. If you have to force-quit, Outlook will offer to resend on next open.
- Still stuck after a restart? It may be a tenant-side block — escalate to whedo.it.
Still stuck after those?
You’ve done the right thing by trying. Send whedo.it a quick note — what you tried, what you saw — and a senior pair of eyes will be on it the same business day.