Messages that are sent-on-behalf-of use the disclaimer details from the assistant

Symptoms

Messages that are sent by an assistant using the "Send on Behalf" of feature of Exchange will use the disclaimer details or signature data from the assistant and not the manager.

Cause

Even though the message is sent on behalf of someone else, it is still sent by the assistant, and this is the information that Exclaimer uses to construct the disclaimer signature data.

Resolution

Use the "Send As" capability of Exchange to do this. Use the Active Directory Users and Computers MMC snap-in to adjust the security properties of the mailbox that the assistant needs to send-as. Add the assistant as a user and confer the "Send As" properties to that person.
The dialog box from our server here shows this clearly.

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