Can't get SMTP to work with Office 365

ryangauer

Been banging my head against this one for a while now, and all the forum posts I've read are old enough that either the settings in osTicket have changed, or microsoft has changed the requirements for connecting to office 365.

After setting up an email address, configuring the server settings and oAuth, when I try to send a message in diagnostics, it fails, and the server logs come back with the "Unable to email via Sendmail Unable to send mail: mail(): SMTP server response: 451 5.7.3 STARTTLS is required to send mail" message.

I've gone through the php.ini settings, and there isn't much in there that I can see either.

[mail function]
; For Win32 only.
; https://php.net/smtp
SMTP = outlook.office365.com
; https://php.net/smtp-port
smtp_port = 587
smtp_ssl=tls

I'm running osTicket 1.18.2 on IIS with php 8.4.6

Anyone have any ideas?

KevinTheJedi

ryangauer

That error means SMTP failed and it tried using local sendmail to send the mail. Review your SMTP settings and ensure it’s connecting successfully. Maybe the client secret expired or something too. Fun fact if you go to the email, go to the Outgoing (SMTP) tab, set the status to Enable, and Save Changes it’ll test the login and will let you know if it failed or not.

Cheers.

ryangauer

I've tried deleting and adding the email address again, and when I configure oAuth, it goes through the MS account sign in and kicks me back to the main portal page. If I go to the /scp page, it let's me in without signing in, and the settings are all there, but when I hit save, it says "Configure Authentication" . I open the config screen and it's all there. The secret was created today, so it's not expired.

The scopes are all enabled in Azure... I tried changing the authorization and token endpoints from the generic URLs to the ones specific to my tenant, and still no change. It says to "configure Authentication", but doesn't tell me what isn't correctly configured.

KevinTheJedi

ryangauer

You getting kicked back to the homepage is the problem. That’s one of a few things:

You misconfigured the app and/or email auth config.
You’re using IIS and don’t have cURL’s root certificate installed so it’s erroring out.
You don’t have the URL Rewrite module installed/enabled on your webserver.

Cheers.

ryangauer

I don't think I misconfigured the app or auth config (I followed any/every example I could find) and SSO with microsoft works to sign in.
The URL rewrite module is installed and enabled.
I installed the cURL root certificate, and it appeared to work for the remote mailbox config, but when I set the SMTP side to use the same auth as the remote mailbox, it comes back (consistently) with an HTTP 500 error.

ryangauer

Quick update: On a lark, I decided to try basic authentication for the outgoing messages, and it worked! I guess I can run with that until Microsoft shuts it down completely.

KevinTheJedi

ryangauer

I imagine they’ll be cutting it off relatively soon as it’s been nearly two years now so it’s better to update it sooner rather than later. 500 is a generic error indicating a deeper issue that should be logged in either PHP error logs or server logs.

Cheers.