Try these checks in classic Outlook and Outlook.com, in order:
- Confirm Outlook is online
- Look at the status bar at the bottom of the Outlook window.
- If it shows Disconnected, Working Offline, or Trying to connect…, go to the Send/Receive tab and select Work Offline once to toggle back online.
- Then select Send/Receive All Folders and see if messages send.
- Verify internet connectivity
- Open a browser on the same PC and go to a site such as
http://www.microsoft.com or http://www.bing.com.
- If websites do not load, fix the network connection first (router, Wi‑Fi, or ISP) before troubleshooting Outlook.
- Check for large or stuck messages
- In classic Outlook, open the Outbox folder.
- Open the oldest message that has not been sent.
- If it has large attachments (typically over 20–25 MB), remove or reduce them, or upload the file to a cloud location and send a link instead.
- Save and send again, then use Send/Receive All Folders.
- Check Outlook.com mailbox and storage
If the account is Outlook.com/Hotmail/Live/MSN:
- Sign in to Outlook.com in a browser.
- Make sure:
- The stuck email is not sitting in Drafts or Outbox.
- The Inbox and Microsoft cloud storage are not full. If full, empty Junk Email and delete or archive old mail to free space.
- Try sending a simple test email (no attachment) to a different address.
- Check for attachment and NDR issues
- If sending fails only for some messages:
- Ensure attachments are under 25 MB in Outlook.com.
- If a non‑delivery report (bounce) arrives, read the reason:
- Invalid address
- Recipient mailbox full
- Recipient server issues
- Spam filters blocking the message
- If the address is correct and it still bounces, follow the guidance in Sender Support in Outlook.com from the referenced article.
- If password was recently changed
- If the email account password was changed on the provider’s website, update the same password in classic Outlook’s account settings so Outlook can authenticate and send.
- If only one device has the problem
- If mail works on web or phone but not on this PC, remove and re‑add or repair the email account/profile in classic Outlook as described in the referenced article (repair Outlook profile / create a new profile).
If these steps do not restore sending, use the Outlook.com interactive troubleshooter and in‑product Help to contact support from within Outlook.com while signed in.
References: