Zammad and Exchange on Premis

Infos:

  • Used Zammad version: 3.3.x
  • Used Zammad installation source: (source, package, …): installed via APT
  • Operating system: Ubuntu 18.04.4
  • Browser + version: Chrome (latest)

Expected behavior:

  • Send E-Mails from Zammad via Exchange

Actual behavior:

  • Zammad wont connect to Exchange Account: “Authentication failed”

I added the same Exchange Account to my Outlook as IMAP Account an IMAP and SMTP is working fine, i can send and recieve E-Mails. On Zammad, i did the same: IMAP working fine, but SMTP always tells me that “Authentication failed”.

Here are my settings:

What am i doing wrong? In Outlook i added the same Account and checked “SMTP needs Auth” and “Same auth as Incomming Mailserver” (or how ever this is called in Englisch Outlook) and the account is working fine there.

Many thanks for the help in advance

Are you sure you can use unencrypted smtp on port 25 with your Exchange? Maybe you have to use port 587 for secure smtp?

Nope, Port 587 is not available on my Exchange and on Port 465 Zammand complains about “SSL_connect returned=1 errno=0 state=error: wrong version number”

I am working with Exchange too. I configured fetching Mails via IMAP and using “sendmail” (Local MTA) for sending. I have postfix installed on the system - configured as “satellite” it works fine …

Sadly, i dont exactly know how to do this.

http://giybf.com/
e.g. look here: https://www.cyberciti.biz/faq/how-to-configure-postfix-relayhost-smarthost-to-send-email-using-an-external-smptd/
Instead of “internet site” you chose “satellite” - as far as I remember you only have to change only the entry for relaying server and your eMail-address (executing relaying only for yout local hostname and 127.0.0.1 - otherwise your building an open relay) - if your exchange accepts anonymous you’re done - otherwise you have to establish authentification which can be done by modifying main.cf => https://www.thomas-krenn.com/de/wiki/TKmon_Relayhost_mit_SMTP_AUTH (german description)

Ok, I have now installed and set up a postfix. E-mail is now working again. Zammad now sends its e-mails to the postfix without authentication and the postfix sends its e-mails to the exchange without authentication… why can’t Zammad send directly to the exchange if I have deactivated the authentication on the exchange for internal stuff?

You’re welcome - it was a pleasure for me to be able to help …

You need to create new SMTP connector on Exchange server to allow Zammad host send mail with correct authentication. In my case it is SMTP TLS on TCP 25.
Do not edit existing connectors, this can cause much trouble, if you not Exchange guru.
P.S. I do not remember, but may be some permissions for receive connector also needed to be set. See below my settings.

Get-ReceiveConnector -Identity “EXCH1\Devices with AUTH SMTPTLS[25]” | fl *

AuthMechanism : Tls, BasicAuth, BasicAuthRequireTLS
Bindings : {0.0.0.0:25}
TlsCertificateName : “YOUR WILDCARD CERT HERE for DOMAIN.TLD”
Enabled : True
PermissionGroups : AnonymousUsers, ExchangeUsers, Custom
RemoteIPRanges : {1.1.2.1, “ZAMMAD IP HERE”}
RequireEHLODomain : False
RequireTLS : False
EnableAuthGSSAPI : False
ExtendedProtectionPolicy : None
LiveCredentialEnabled : False
Name : Devices with AUTH SMTPTLS[25]

Get-ADPermission -Identity “Devices with AUTH SMTPTLS[25]” | where {($.Deny -eq $false) -and (
$
.IsInherited -eq $false)} | Format-Table User,ExtendedRights

User ExtendedRights


NT AUTHORITY\ANONYMOUS LOGON {ms-Exch-SMTP-Accept-Any-Sender}
NT AUTHORITY\ANONYMOUS LOGON {ms-Exch-SMTP-Accept-Authoritative-Domain-Sender}
NT AUTHORITY\ANONYMOUS LOGON {ms-Exch-SMTP-Accept-Any-Recipient}
NT AUTHORITY\ANONYMOUS LOGON {ms-Exch-SMTP-Submit}
NT AUTHORITY\ANONYMOUS LOGON {ms-Exch-Accept-Headers-Routing}
NT AUTHORITY\ANONYMOUS LOGON {ms-Exch-Bypass-Anti-Spam}
NT AUTHORITY\Authenticated Users {ms-Exch-Accept-Headers-Routing}
NT AUTHORITY\Authenticated Users {ms-Exch-Bypass-Anti-Spam}
NT AUTHORITY\Authenticated Users {ms-Exch-SMTP-Accept-Any-Recipient}
NT AUTHORITY\Authenticated Users {ms-Exch-SMTP-Submit}
NT AUTHORITY\Authenticated Users {ms-Exch-SMTP-Accept-Any-Sender}
NT AUTHORITY\ANONYMOUS LOGON {ms-Exch-SMTP-Accept-Any-Sender}
NT AUTHORITY\ANONYMOUS LOGON {ms-Exch-SMTP-Accept-Authoritative-Domain-Sender}
NT AUTHORITY\ANONYMOUS LOGON {ms-Exch-SMTP-Accept-Any-Recipient}
NT AUTHORITY\ANONYMOUS LOGON {ms-Exch-SMTP-Submit}
NT AUTHORITY\ANONYMOUS LOGON {ms-Exch-Accept-Headers-Routing}
NT AUTHORITY\ANONYMOUS LOGON {ms-Exch-Bypass-Anti-Spam}
NT AUTHORITY\Authenticated Users {ms-Exch-Accept-Headers-Routing}
NT AUTHORITY\Authenticated Users {ms-Exch-Bypass-Anti-Spam}
NT AUTHORITY\Authenticated Users {ms-Exch-SMTP-Accept-Any-Recipient}
NT AUTHORITY\Authenticated Users {ms-Exch-SMTP-Submit}
NT AUTHORITY\Authenticated Users {ms-Exch-SMTP-Accept-Any-Sender}

===========================================================================

The SSL error is either due a too old SSL cipher Zammad tries to use or a very new one.
Answering “why” is in this case impossible, because we know too little about your MTA configuration to provide a good answer on that.

A good start would to check your enabled MTA ciphers.
That is if this is still a relevant topic for you.

we currently have the same problem!
but we want send without TLS directly from zammad

This is a question of transport configuration.
That’s perfectly possible with exchange.

And you want to tell me the configuration?

Setup a receive connector for SMTP that either requires (or does not require) authentication. In the same dialogue you can also decide to use TLS or not. Ensure to tighten the network ranges correctly.

Further input to that topic:

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