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

**URL:** <https://community.ciphermail.com/t/pgp-subject-signing-trigger-behaves-differently-in-ciphermail-6-5-than-in-5-4/1069>\
**Category:** Gateway\
**Tags:** pgp\
**Created:** [October 30, 2026, 4:47pm UTC](https://community.ciphermail.com/t/pgp-subject-signing-trigger-behaves-differently-in-ciphermail-6-5-than-in-5-4/1069 "2026-10-30T16:47:23Z")\
**Posts on this page:** 3\
**Page:** 1

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**Author:** ![schoppeit](https://dub1.discourse-cdn.com/flex017/user_avatar/community.ciphermail.com/schoppeit/32/163_2.png) [@schoppeit](https://community.ciphermail.com/u/schoppeit)\
**Post date:** [October 30, 2026, 4:47pm UTC](https://community.ciphermail.com/t/pgp-subject-signing-trigger-behaves-differently-in-ciphermail-6-5-than-in-5-4/1069/1 "2026-10-30T16:47:23Z")

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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

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<div class="post-metadata">

**Author:** ![martijn](https://dub1.discourse-cdn.com/flex017/user_avatar/community.ciphermail.com/martijn/32/127_2.png) [@martijn](https://community.ciphermail.com/u/martijn)\
**Post date:** [October 30, 2026, 5:25pm UTC](https://community.ciphermail.com/t/pgp-subject-signing-trigger-behaves-differently-in-ciphermail-6-5-than-in-5-4/1069/2 "2026-10-30T17:25:09Z")

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

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<div class="post-metadata">

**Author:** ![schoppeit](https://dub1.discourse-cdn.com/flex017/user_avatar/community.ciphermail.com/schoppeit/32/163_2.png) [@schoppeit](https://community.ciphermail.com/u/schoppeit)\
**Post date:** [October 30, 2026, 7:49pm UTC](https://community.ciphermail.com/t/pgp-subject-signing-trigger-behaves-differently-in-ciphermail-6-5-than-in-5-4/1069/3 "2026-10-30T19:49:12Z")

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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?