PGP subject signing trigger behaves differently in CipherMail 6.5 than in 5.4

Hello,

I am running CipherMail Community Gateway 6.5.0.0g55060922. I want outgoing emails to be signed with PGP only when the subject contains (s). Emails without (s) should remain unsigned.

This worked as expected with CipherMail 5.4. In that version, I had “Only sign when encrypt” enabled and “Skip signing only” disabled. With those settings, the subject trigger signed messages containing (s), while messages without the trigger remained unsigned.

In version 6.5, I cannot get the same behavior. The PGP subject signing trigger is enabled with the regular expression \(s\). The trigger is detected in the backend log, and the matched text is removed from the subject as configured. PGP is enabled, PGP/MIME is selected for outgoing messages, and S/MIME is disabled for the sender. A PGP signing key is present and assigned to the sender address. There are no individual user settings for the recipient.

The “Skip Sign Only” setting produces this behavior in version 6.5:

  • Enabled: No message is signed, including messages whose subject contains (s).

  • Disabled: All outgoing messages are signed, including messages without (s).

Despite the trigger being detected, the message is delivered without a PGP signature.

Has the behavior or meaning of “Only sign when encrypt” or “Skip signing only” changed between versions 5.4 and 6.5? Is there a setting in version 6.5 that provides the same behavior as my version 5.4 configuration?

Kind regards,

André

Are you absolutely certain this worked with V5.4? Because I think this only worked with S/MIME.

Yes, I am absolutely certain. We have been using this configuration for years. We currently have 10 users (senders) with PGP keys. A PGP key is only created for a sender when a signature is triggered via the subject line. I tested this again today. At the moment, CipherMail 5 is in production, while CipherMail 6 is being used in a test environment.

If I re-enable the “skip-sign-only” option, how else can I trigger the creation of a signature?