I CAN send a test message using Outlooks built in test feature. I can also send email from the command line using telnet to the ISP's mail server on port 25. This always works.

You can fix Sending and Receiving reported error (0x800CCC69), Unknown Error 0x800CCC69 in Outlook by reconfiguring SMTP settings.

If you can't reply or forward an email on Outlook due to Cannot send this item error, make sure your Outlook is up-to-date and then use these fixes.