#3338 new
Maximilian Held

s/mime signed emails are flagged as "tampered with" by gmail

Reported by Maximilian Held | March 5th, 2024 @ 07:01 PM

I have an S/MIME certificate on my mac.

Here's the combination of what works and does not work:

  1. Sending a signed email from Mail.app to a gmail.com account: works; gmail UI shows green check mark.
  2. Sending a signed email from MailMate.app to an iCloud.com account, retrieving on another mac with Mail.app: works, UI indicates all is fine with the certificate.
  3. Sending a signed email from MailMate.app to a gmail.com account: gmail UI marks Email as "tampered with".

Between these combinations it would appear that MailMate is a necessary condition (though not sufficient) for this problem to arise.

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Mac OS X email client.

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