Hello I try to use Office365 as SMTP for discourse. I’m already using this account for my wordpress SMTP so the account is not the problem. When i try to send a email test, an error message appear [Sender] 504 5.7.4 Unrecognized authentication type [AM3PR05CA0123.eurprd05.prod.outlook.com] This is my SMTP config from app.yml ## TODO: The SMTP mail server used to validate new accounts and send notifications DISCOURSE_SMTP_ADDRESS: smtp.office365.com DISCOURSE_SMTP_PORT: 587 DISCOURSE_SMTP_USER_NAME: test@example.fr DISCOURSE_SMTP_PASSWORD: password DISCOURSE_SMTP_AUTHENTICATION: login DISCOURSE_SMTP_ENABLE_START_TLS: false Any idea how to fix the problem ? Another config: ## TODO: The SMTP mail server used to validate new accounts and send notifications DISCOURSE_SMTP_ADDRESS: smtp.office365.com DISCOURSE_SMTP_PORT: 587 DISCOURSE_SMTP_USER_NAME: test@example.fr DISCOURSE_SMTP_PASSWORD: password DISCOURSE_SMTP_AUTHENTICATION: login DISCOURSE_SMTP_ENABLE_START_TLS: true I get the following error: 550 5.7.60 SMTP; Client does not have permissions to send as this sender The problem is from Discourse, because I can test with swaks and it’s working swaks --to test@example.com --from test2@example.com --server smtp.office365.com --auth login --auth-user test2@example.com -tls

Okay the problem is now fixed. Huge mistake from my side : the email from Admin → settings → notification email was not the same from the smtp username. Maybe a check should be made to prevent user to makes this mistake :face_with_raised_eyebrow: but it seems like DISCOURSE_SMTP_AUTHENTICATION: login isn’t required True, the final config DISCOURSE_SMTP_ADDRESS: smtp.office365.com DISCOURSE_SMTP_PORT: 587 DISCOURSE_SMTP_USER_NAME: test@example.fr DISCOURSE_SMTP_PASSWORD: password DISCOURSE_SMTP_AUTHENTICATION: login DISCOURSE_SMTP_ENABLE_START_TLS: true

[image] Chopper: DISCOURSE_SMTP_AUTHENTICATION: login DISCOURSE_SMTP_ENABLE_START_TLS: false Not Suggesting that You use office365 for SMTP but it seems like DISCOURSE_SMTP_AUTHENTICATION: login isn’t required … maybe try commenting that out and try again with STARTTLS set to True?

[image] Chopper: Maybe a check should be made to prevent user to makes this mistake Discourse cannot guess what addresses the mail server will deliver for.

[image] Chopper: True, the final config DISCOURSE_SMTP_ADDRESS: smtp.office365.com DISCOURSE_SMTP_PORT: 587 DISCOURSE_SMTP_USER_NAME: test@example.fr DISCOURSE_SMTP_PASSWORD: password DISCOURSE_SMTP_AUTHENTICATION: login DISCOURSE_SMTP_ENABLE_START_TLS: true Sadly this solution is not working for me (I also tried to escape the password). I tried it with this SMTP setting problem with Office365 - #5 by ianwhite one which is working. But not everybody gets E-Mails… :thinking:

If some people get mail then it’s the fault of office365, or their mail provider. The others should check their spam folder, though if they use a service life office365 it will silently drop mail that it thinks is spam.

[image] Chopper: True, the final config DISCOURSE_SMTP_ADDRESS: smtp.office365.com DISCOURSE_SMTP_PORT: 587 DISCOURSE_SMTP_USER_NAME: test@example.fr DISCOURSE_SMTP_PASSWORD: password DISCOURSE_SMTP_AUTHENTICATION: login DISCOURSE_SMTP_ENABLE_START_TLS: true I tried it with these settings. In the skipped section in the email tab I can see the following error: 554 5.2.0 STOREDRV.Submission.Exception:SendAsDeniedException.MapiExceptionSendAsDenied;

Sounds like the address you are sending from is not one that the mail server supports. There is a line at the bottom of app.yml that week let you set the notification address. (you can set it in sure settings if you’re logged in)

Or maybe they have VERP enabled so the email address is replies+{key}@example.com instead of the authorized noreply@example.com That was the issue I’ve faced in past while trying to send mails from my own mail server. It’s usually easy to fix though.

Yes. This worked for me. Two things in the initial setup: DISCOURSE_SMTP_USER_NAME: -- AND -- DISCOURSE_NOTIFICATION_EMAIL: needed to be set to the same email.

Some up to date instructions for anyone struggling with office365 & direct-delivery Go to Microsoft admin center Click on Settings then Domains Click on Add Domain Follow the instructions on the screen to add your forum’s URL (example: forum:yourlinks.com) Once you’ve completed the above steps and the DNS is verified, you’re now able to create an inbox using that subdomain Click on Users and then Active users Click on Add a user Create the mailbox for your forum (example: noreply@forum.yourlinks.com) mailbox domain must match the hostname from where the forum runs Click on Licenses & Apps Assign this mailbox an Exchange Online (Plan 1) license (10,000 messages daily 30msg/min throttle) It is required to have a license attached to the mailbox for the purpose of direct-delivery. At the time of writing, the cost is $4.00USD/mo or $5.10/CAD | Should you require a higher limit or a shorter throttle, there are other plans available Click on Mail and then Manage email apps Enable “Authenticated SMTP” Click Save changes Go to your Azure portal Browse to your active directory Select Properties in the left sidebar, right under User settings Select Manage security defaults Set Security defaults to “disabled” Click save Go back to Users > Active users Click on Multi-factor authentication Disable MFA on the mailbox being used The mailbox is now ready for use by your Discourse.

SMTP with office365?

Product Support Self-hosting

RPGpro (Adam Kelsall) August 17, 2023, 1:00pm 12

Set Security defaults to “disabled”

This was the one thing that was stopping SMTP auth…
Been banging my head against a wall for days…
Why do MS make things so difficult…?

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SMTP with office365?

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