Email connectivity with Exchange Server


  • Used Zammad version: 5.1.x
  • Used Zammad installation type: Debian
  • Operating system: Debian 10
  • Browser + version: Firefox 100.0, M$ Edge 101.0.1210.32

Expected behavior:

  • On creation of new ticket or update - expect Agent and User email notification
    (using M$ Exchange 2010 Server as MX relay)

Actual behavior:

  • No emails sent - however 'New Ticket - test email is created and sent at every reboot.
    After ‘x’ number of days I will get an SMTP 550 - can not relay message in the Outbound settings for Email settings. After running through the setup again in Outbound wizard, it reconnects - but still not sending ticket updates or new messages.

Steps to reproduce the behavior:

I have checkout the FQDN setting suggestions in this forum. Under the Monitoring section Current Status, I see 29 Failing background jobs.
Failed to run background job #1 ‘SearchIndexAssociationsJob’ 9 times with 116 attempts.
Failed to run background job #2 ‘SearchIndexJob’ 2 times with 38 attempts
Those stats on a fresh reboot.

Let me know what Logs can post. I’m a tenderfoot Admin with Debian so I would be grateful newbie instuctions :slight_smile:

The basically means your Exchange server says ‘nope, I won’t deliver this message’ to your Zammad server.

Check the logs of your Exchange for the reason. Maybe a rate limit? Sender (domain/relay) limitations?

Thanks - yes I’ve been looking at this and not finding much a the exchange end.
What is the process of checking the queues (?) from the Debian/Zammad side to see if there are some messages there.
Like I mentioned - that 550 errors are intermittent. When I’m not getting that error I’m still not seeing a mail flow BUT I am getting the generic ‘test’ email.
Thanks for the reply.

There is no queue. Zammad acts (more or less) like a normal email client, it gets messages with IMAP and sends them with SMTP.

You have to find the reason for the 550 (there are many different types).

Thanks Tom. I’ll keep digging between jobs and report back. I think I might see an issue on the Exchange end. I am right in thinking emails should be sent on update of tickets correct? And I’m not sure that those monitoring ‘errors’ are normal. I don’t have a baseline to go by as I try to introduce more Open Source into our company and continuing my training in Linux.

Appreciate the feedback, Cheers Barry.

This depends on the settings in the profile. An agent can normally customise the notification behaviour.

You can check what has been sent when and to whom for every ticket.
Open a ticket and choose ‘Ticket’ → ‘History’ in the top right of the view.

I have had the chance to follow up on this and found the AD user in exchange has a few issues. Upon recreation of the ‘support’ user account and creating the exchange mailbox it seems to be done now as to how to setup the outbound SMTP setting. We don’t need authentication to send mail internally but Zammad returns and ‘End of file reached’ error when leaving the user name and/or password blank.

Doing a little digging to see what that might be about.

Hmm… if I telnet from an other Ubuntu workstation using the support@domain_name I can continue and send email - pointing at the Exchange Server. However if I try the same thing from a terminal on the Zammad server running on Debian I get user could not be authenticated message and the telnet session is closed…

Check your receive connectors i would say.
Is the zammad server located in an other subnet/network as the ubuntu workstation?
Maybe even a router in between?

can you send from workstation, from internal to internal? and from internal to external? and from external to internal?
can you do the same from the zammad server?

default exchange config, will allow you to send from int to int, without authentication,
you can even send from ext to int (as if you are an outsider) without authentication,
but if you want to send from internal to external, default you have to authenticate.

at this moment we have different config, so cant really make easy tests.
(we use exchange-imap to poll, and smtp from our spamfilter with auth to send).

Note: no zammad expert, just trying to help.

Great suggestions that I will follow up on GK. might take me a bit with a holiday coming up next week but Ill post my findings. But to tick off a couple of these already. Yes on same subnet. Checked Receive Connectors. this is an all int to internal setup at the moment. If I bang my creds into Zammad it seems to work for a while but still not emails.

I’m checking everything under the my profile to see if I can generate some mail but its still spotty with only system level test mail coming through.

Appreciate the ideas folks - would love to make this work.

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