Relevant Products: Exclaimer Cloud - Signatures for Office 365
An email message is comprised of headers and body content. When a message is transmitted, the whole thing (headers and body) is wrapped in an envelope. The envelope specifies what system is transmitting the mail, who it is from and who it is being sent to.
When automatic replies are sent from Office 365, MAIL FROM: information for the envelope is set to <> - i.e. there is no MAIL FROM: information.
This means that automatic replies trigger an exception in the transport rule that identifies messages to send to the Exclaimer Cloud - these messages are not routed to the Exclaimer Cloud and so no signature is applied.
Unfortunately, it is not possible to use Exclaimer Cloud to apply signatures to out of office messages or automatic replies at the moment.
However, we are investigating methods to allow this in a future release of the software.