Here are a couple quick tests you can do to troubleshoot issues sending mail from outlook.
1) Log into webmail: http://mail.
2) If the problem is with Outlook (you receive the test email sent from webmail), then there are a couple of common fixes you can try first.
- Reset the Outbox
- Move all emails in the Outbox to another folder so they are not trying to send.
- Close Outlook and then re-open it
- Create a new test message to send to your external email account (i.e. Gmail, Yahoo, etc.).
- If the email to the external accounts goes through, then the problem is normally that Outlook choked on one of your outgoing emails.
- If this is the case, you'll need to test each one of the emails that was in the outbox to see which one is causing the problem. Often large attachments will be the hang-up.
- Open each message, one at a time, and try to send. If it gets stuck, that's the one causing the problem. Move it back out of the outbox and test the rest.
- For any messages that don't send, check to see if you have an attachment that is causing them problem. If the attachment is too large, use https://wetransfer.com/ or another service to send the file.
- Restart the Computer
- If the steps to Reset the Inbox don't take care of the problem, close outlook and restart the computer.
