Office 365 authentication error

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OTRS newbie
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Joined: 16 Apr 2019, 17:14
OTRS Version?: otrs-6.0.17

Office 365 authentication error

Post by demoncrest »

Good day dear please I require your support.

I have the following problem

ERROR: :: Email :: MailQueue-67 Perl: 5.16.3 OS: linux Time: Tue Apr 16 09:45:20 2019

Message: CommunicationLog (ID: 157440, AccountType: -, AccountID: -, Direction: Outgoing, Transport: Email, ObjectLogType: Connection, ObjectLogID: 300720) :: Kernel :: System :: Email :: SMTP => SMTP authentication failed ( SMTP code: 500, ErrorMessage: 500, Command unknown: 'AUTH').

The Office credentials are correct as the user.

Thanks for the support

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Real Name: Alexey Yusov
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Re: Office 365 authentication error

Post by alexus »

Try to use SMTPS or SMTPTLS
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OTRS newbie
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Joined: 16 Apr 2019, 17:14
OTRS Version?: otrs-6.0.17

Re: Office 365 authentication error

Post by demoncrest »

Good day friend in cases is SMTPS or SMTPTLS the error persists that can happen?

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Re: Office 365 authentication error

Post by crythias »

Maybe set up a connector in Office365 that allows your OTRS WAN IP address without authentication.
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Re: Office 365 authentication error

Post by ezoltan »


As many others have found, OTRS Community has trouble authenticating to O365.

I tried all available options (SMTP, SMTPS, SMTPTLS) along with Option 1 and Option 3 as per ... g-office-3. With or without the custom connector, no go (sorry crythias, unfortunately that didn't work).

Here is what worked for me:
- Found that postfix was already present on my brand-spenking-new Centos7 Minimal Install with OTRS installed and configured, so I thought I'll use it as relay/smarthost to O365.
- Configured postfix to authenticate to O365 and to use TLS, as described in many forums, such as ... relay.html
- Configured OTRS to send notifications to localhost using SMTP (no encryption)

The idea is that OTRS sends the notification to an SMTP MTA which happens to be postfix installed on the same machine, which, in turn, relays it to O365 via an authenticated session.

Happy to confirm that it worked a treat.

The drawback is that I need an Exchange Online mailbox and thus I am burning a license. However I use that same mailbox to fetch ticket request emails, so it doesn't concern me that much.

In order to save the license, I believe the following setup would also work (didn't test it though)

1. Install a local postoffice (e.g. dovecot) and create a mailbox. Configure OTRS to fetch emails from this mailbox.
2. Install/configure a local MTA (e.g. postfix) that can handle incoming SMTP traffic.
3. Configure mail routing between O365 and the local MTA as per ... route-mail.
4. (Optional) Lock down inbound SMTP traffic from O365 only, so that your OTRS inbox doesn't get abused (reduce the attack surface on inbound TCP 25). For the URLs and IP addresses used for this purpose see ... nge-online.
5. Add your public IP address, from which OTRS emails originate, to your domain's SPF record.

Your should be ready to rock and roll.

Hope this helps.
See you at

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