Office365: Can't use Channel::Driver::Smtp: #<NoMethodError: undefined method .."

Infos:

  • Used Zammad version: 6.1.0-1698142833.c4a2d029.bullseye
  • Used Zammad installation type: package
  • Operating system: Debian Bullseye
  • Browser + version: Google Chrome 118.0.5993.118

Expected behavior:

  • To sent the reply on a ticket.

Actual behavior:

  • Most of the replies are sent without problems, but sometimes the it fails with the error:

Aflevering mislukt (translation : delivery failed):
“Unable to send email to ‘user@ourdomain.nl,user2@ourdomain.nl’:
Can’t use Channel::Driver::Smtp: #<NoMethodError: undefined method `force_encoding’ for nil:NilClass body attachment.content.force_encoding(‘BINARY’) ^^^^^^^^^^^^^^^>”

Steps to reproduce the behavior:

  • The reproduction seems to be very hard because it looks like it is something random.

But any help in finding a cause and/or solution would really be appriciated.

Please update to the latest available Zammad version.
Ensure that your database migrations have run completely.

Constructing a email with a to like this: user@ourdomain.nl,user2@ourdomain.nl will most likely give you a 100% based reproduction rate. If that’s the case try to find the ticket and the fitting article. If I’d have to guess it’s actually “one” address containing both addresses which syntactically is invalid.

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