Configure a Distribution Group to send a reply message every time (Not an Out-of-Office Message)

Scenario: You need a distribution group to send a ‘specific’ reply message back to the sender, every time a sender sends to it. An Out-of-Office message will not do because it will only send a reply one time.

Note: Distribution Groups do not have this functionality, however there is a work around with using a shared mailbox.

1. Create a Shared Mailbox that will host sending the reply messages. We will call it:

2. Log into an Outlook client as the shared mailbox and create the following inbox rule:

“Apply this rule after the message arrives
have server reply using “blah blah blah

3. Even though this is a Inbox Rule, set your Distribution Group so it allows sending Out-of-Office (OOF) messages which is turned off by default. This is required for return messages:

Set-DistributionGroup -SendOofMessageToOriginatorEnabled:$true

4. Create a Transport Rule OR add that shared mailbox to your distribution list. I chose the Transport Rule because it is cleaner to the end users — they wont start asking questions about this new account. We are using the AnyOfToCCHeader to trigger the rule if it the Distribution list is sent to.

New-TransportRule -name “BCC_Reply” -AnyOfToCCHeader -blindcopyto