Outgoing responses from Zammad flagged as junk mail

Technical assistance
1

So we have noticed something annoying with our setup.

When we respond to an issue created by a customer (issues are created via e-mail), sometimes it seems the customer doesn’t see our responses.

It has happened often enough that we were starting to see a pattern and the issue appears to happen when the customer writes us from (and we respond to) a hotmail address. I assume this would happen with other microsoft domains as well.

We tried this ourselves with a private hotmail account and what we found was that when we responded from Zammad, the response ended up in the junk mail folder in the hotmail (outlook) web client.

This does not happen with any other e-mail provider that we have tested with.

Our setup is that we use a google workspace account for receiving and sending e-mails in Zammad.

The google workspace account has a number of aliases (support@ info@ etc) which are also defined in the Google channel in Zammad.

Interesting thing is that if we log in gmail with the google workspace account and respond to the client e-mail from there, it does NOT get flagged as junk mail for the customer.

So
Respond to a customer e-mail from Zammad to a hotmail address → Junk
Respond to a customer e-mail from gmail to a hotmail address (same account and alias as above) → not junk.

Has anyone else seen this and if so, how did you resolve it?

Steps to reproduce the behavior:

  • Set up a google account to use with zammad with an alias
  • Set up the google account in Zammad
  • Set up a filter to assign e-mails to this alias to a group that uses the same alias
  • Send an e-mail to the alias from a hotmail account
  • Respond to the issue through Zammad
  • The respons will end up in the Junk folder of the hotmail account
2

Email being flagged as spam is not an issue of your email Client (Zammad in this case), but generally the following:

  • the content of the mail
  • bad IP reputation of your MTA / bad MTA reputation in general
  • poor Domain configuration in terms of mail security (aka SPF, DKIM and DMARC)
1 Like
3

Ask one of your customers who has experienced this to send you the full e-mail headers. Most anti-spam software will add the reason(s) why the e-mail is considered to be spam to the header information (e.g. “spam result” or “spam score”), and it usually boils down to the problems mentioned by MrGeneration.