Signatures Not Applied to Moderated Distribution Group Emails

When emails are sent to moderated distribution lists, signatures may not be applied by Crossware. This behaviour is expected due to how message approval workflows function within Microsoft 365.


Cause

In moderated distribution groups, emails are first routed to a moderator for approval before being delivered to recipients. During this process:

  • The original message is held for approval

  • Once approved, Microsoft 365 resubmits the message

  • The resubmitted message may bypass the normal transport path where Crossware applies signatures

Because Crossware applies signatures during the mail flow (transport) stage, the resubmitted message may not pass through the same processing point, resulting in no signature being added.


Impact

  • Emails sent to moderated distribution groups may be delivered without a signature

  • This only affects messages that require approval before delivery

  • Standard distribution groups (without moderation) are not affected


Solution / Workarounds

Option 1: Apply signatures client-side

Use Crossware Client-Side Signatures to ensure signatures are added before the email is sent:

  • Signature is inserted by the user before sending, becoming part of the email body and not relying on transport rules.

  • Ensures the signature is present before moderation occurs


Option 2: Modify the transport rule

Update the transport rule so it applies to all internal senders rather than a specific group. This increases the likelihood that signatures are applied to emails sent to moderated distribution groups.

  1. Sign in to your Exchange Admin Center.

  2. From the left-hand navigation menu, select Mail flow, then select Rules.

  3. Open the transport rule used for Crossware.

  4. Remove the condition The sender is a member of (if present).

  5. Add the condition Apply this rule if: The sender is located is set to In Organisation.

  6. Save your changes.

Changing this setting may increase the number of users whose emails are processed by Crossware, as the rule will apply to all internal senders rather than a defined group.

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