Hi there,
We have been using the S/MIME Encryption for quite some time now ( > 1 Year)
Recently a few users told me about problems with the Encryption.
They can't communicate encrypted with some external users.
After some research, we found out that the certificate is missing in the S/MIME Certificates List.
We currently have 330 Certificates in this list, if it matters.
We then tried to replicate the error. So i created a new S/MIME Certificate via COMODO for my private mail account and send it to my work-mail.
The mail arrived, was signed and no certificate was extracted at the UTM.
I answerd on to this mail (Work -> Private) and got a signed mail on my private mail account.
I added the work-certificate and answered encrypted. The Mail got delivered was decrypted... Wait what? Yes, It got the [ENCRYPTED] Tag from the Sophos UTM, the content of the mail is readable in mail-client.
Ok next step, send a mail back (Work - Private)... Only signed, not encrypted, mail from Private - Work... again encrypted.
Currently we are on UTM 9.600-5, tested the communication via Outlook 2016 (Work) and iPhone (Private).
Does anyone else have a problem like this? Would love to hear a solution for thiis.
I have the debuglevel logfiles if needed.
Kind regards
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