# Outlook SMTP Server Issues (SMTPSyntaxError)

**URL:** <https://meta.discourse.org/t/outlook-smtp-server-issues-smtpsyntaxerror/296414>\
**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:** 3

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**Author:** ![bluiavato](https://avatars.discourse-cdn.com/v4/letter/b/71c47a/32.png) [@bluiavato](https://meta.discourse.org/u/bluiavato)\
**Post date:** [February 23, 2024, 5:19pm UTC](https://meta.discourse.org/t/outlook-smtp-server-issues-smtpsyntaxerror/296414/3 "2024-02-23T17:19:18Z")

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Hi Michael,

Thanks for your suggestion, but it seems to give the same error it gives when I use ./discourse-doctor.

```plaintext
root@discourse-app:/var/www/discourse# rake 'emails:test[brian.lui@foo.co]'
Testing sending to brian.lui@foo.co using foo.mail.protection.outlook.com:25, username:user@foo.co with login auth.
======================================== ERROR ========================================
                                    UNEXPECTED ERROR

Net::SMTPSyntaxError

====================================== SOLUTION =======================================
This is not a common error. No recommended solution exists!

Please report the exact error message above to https://meta.discourse.org/
(And a solution, if you find one!)
=======================================================================================

```

Brian

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