Outlook SMTP Not Working

[james.noxon (Brad)]

I’m at a loss. I’m using Outlook as the mail system for my discourse setup which is self-hosted. Doctor keeps saying its an auth issue, however, when I test the SMTP through another service just to see if the settings are valid, it passes, so clearly something going on with Discourse on my end. Can anyone login to my service and test it? I have a feeling it has to do with Outlooks auth system “STARTTLS and OpenAuth”

[Arkshine]

Hey brad, welcome!

I think this guide might help you:

Troubleshoot email on a new Discourse install

You just installed Discourse via the install guide, but email doesn’t seem to work. Unfortunately this means you can’t log in as an admin to finalize the install. Let’s troubleshootize! Try the doctor If you run ./discourse-doctor it will check several ways that your mail configuration might be broken, and offer advice. Try that first. Did you enter email settings correctly? The simplest way is to run ./discourse-setup again. Did you enter everything correctly? B…

[tvavrda (Tomas Vavrda)]

Do you mean outlook.com? I think it will block your e-mails very soon as it is not made for sending this kind of e-mails. Same for Gmail. You need to use some of the professional SMTP services (Sendgrid, Mailgun, etc.).

[rogerreed]

If your STMP configuration is working for others clients, it is most probably a problem in the Discourse SMTP setup, not an Outlook issue. Please make sure STARTTLS, method of authentication and the port match the settings in Outlook. Please check Discourse logs for any detailed error.