M365 SMTP settings

[StefanRower]

Hi, my question is Micrsosoft 365 based.
I'm stucking in the configuration for e-mailalerts.
I configured M365 fpr testing organization wide an /or the account vor using authenticated SMTP.
I tested the functionalaty with Thunderbird and was able to send mails over authenticated SMTP.
Wenn I try same thing in Tactical RMM I get a message, that

With Set-TransportConfig -SmtpClientAuthenticationDisabled $true:
(535, b"5.7.139 Authentication unsuccessful, user is locked by your organization's security defaults policy. Contact your administrator. [FR0P281CA0244.DEUP281.PROD.OUTLOOK.COM 2024-07-31T10:06:51.744Z 08DCB10A2A487CAC]")
400: Bad Request

With Set-TransportConfig -SmtpClientAuthenticationDisabled $false:
(535, b"5.7.139 Authentication unsuccessful, user is locked by your organization's security defaults policy. Contact your administrator. [FR3P281CA0039.DEUP281.PROD.OUTLOOK.COM 2024-07-31T10:07:37.047Z 08DCB05D082128A7]")
400: Bad Request

The user self is able to use authenticated SMTP to:

PS C:\WINDOWS\system32> Get-CASMailbox -Identity *******@sv-richardson.de | Format-List SmtpClientAuthenticationDisabled
SmtpClientAuthenticationDisabled : False

The user isn't locked cause everthing else works fine an in M365 Administrator I'm able to lock this user. Unlock ist not shown like it is, when the users forget their passwords and try hard to log in ;-)

Best wishes
Stefan

[dinger1986]

check what security defaults is blocking, you can also do it this way https://docs.tacticalrmm.com/functions/emailsms_alert/#setting-up-tactical-rmm-alerts-using-open-relay

[StefanRower]

thx dinger,
I'm very sure, there is no policy an M365 site blocking me. Cause Thunderbirds works normaly.
As old mailserver (postfix) open relay makes bad vibes ;-) But on the other hand, is opening M365 security policies is not a good idea ether.
I will try open relay cause it seemes legit. :-D

[dinger1986]

Thunderbird uses OAuth I am sure

[StefanRower]

You can choose:

I choose password, normal

[dinger1986]

open relay is fine as you secure it to the IP

[StefanRower]

At least something changed gg

(451, b'5.7.3 STARTTLS is required to send mail [FR0P281CA0177.DEUP281.PROD.OUTLOOK.COM 2024-07-31T12:01:51.756Z 08DCB10BDD915035]', '[email protected]')
400: Bad Request

Using telnet from the rmm-machine same error:

TacticalRMM:~# telnet outlook.office365.com 587
Trying 40.99.149.130...
Connected to outlook.office365.com.
Escape character is '^]'.
220 FR2P281CA0063.outlook.office365.com Microsoft ESMTP MAIL Service ready at Wed, 31 Jul 2024 12:07:53 +0000 [08DCB0F27524376D]
helo rmm.sv-richardson.de
250 FR2P281CA0063.outlook.office365.com Hello [37.24.67.55]
mail from: [email protected]
451 5.7.3 STARTTLS is required to send mail [FR2P281CA0063.DEUP281.PROD.OUTLOOK.COM 2024-07-31T12:08:18.400Z 08DCB0F27524376D]Connection closed by foreign host.
Fortunaly I speak SMTP g

Now we have the salad, I think me kicks a horse.

[dinger1986]

Need to use port 25 for open relay

[StefanRower]

Yes, I tested this to with same result.

[dinger1986]

Did you allow the IP?

[StefanRower]

Yes of course. The server is on premise here in our building and we we use a static IP.

[dinger1986]

I guess what I am saying is I know that guide works cause that's how mine is setup.

Regards,
Daniel

[silversword411]

If this needs updating
https://docs.tacticalrmm.com/functions/emailsms_alert/#setting-up-tactical-rmm-alerts-using-open-relay

please do a PR or writeup a summary and I'll update

[dinger1986]

It doesn't