# Outlook SMTP Server Issues (SMTPSyntaxError) **URL:** \ **Category:** Self-hosting\ **Tags:** email\ **Created:** [February 23, 2024, 1:04am UTC](https://meta.discourse.org/t/outlook-smtp-server-issues-smtpsyntaxerror/296414 "2024-02-23T01:04:28Z")\ **Posts on this page:** 1\ **Showing post:** 2
**Author:** ![supermathie](https://sea3.discourse-cdn.com/meta/user_avatar/meta.discourse.org/supermathie/32/507518_2.png) [@supermathie](https://meta.discourse.org/u/supermathie)\ **Post date:** [February 23, 2024, 1:35am UTC](https://meta.discourse.org/t/outlook-smtp-server-issues-smtpsyntaxerror/296414/2 "2024-02-23T01:35:00Z")
> [@bluiavato](#): > > However, this is where I’m a bit stuck since I am unable to create my first user since the SMTP settings I’m using seem to not work and is constantly throwing a `Net::SMTPSyntaxError`, not matter what I try. I would advise to dump the traffic going from your container to the SMTP server so you can see exactly what’s happening on the wire. You can trigger an email by running inside the container: ```plaintext rake 'emails:test[your.email.address@your.domain]' ``` and you should see e.g.: ```plaintext root@michael-discourse-docker-app:/var/www/discourse# rake 'emails:test[michael@contoso.com]' Testing sending to michael@contoso.com using mail.contoso.net:587, username:michael with plain auth. SMTP server connection successful. Sending to michael@contoso.com. . . Mail accepted by SMTP server. Message-ID: e7adb5c4-f404-4800-b070-631b06ff5335@mx1.contoso.com ``` Which might also give you some clues. --- _[View the full topic](https://meta.discourse.org/t/outlook-smtp-server-issues-smtpsyntaxerror/296414)._