I'm working in an environment where external auto-forwarding isn't generally allowed unless there's a compelling reason for exceptions. Currently, we have a transport rule in place that permits certain email addresses to forward, but it's maxed out just under the 8KB limit, meaning no more addresses can be added. This rule has a priority of 10 and doesn't have the 'stop processing rules' option checked.
Recently, we were asked to add three more addresses, but since we can't modify the existing rule, we cloned it and assigned a new priority of 11 to the clone. However, having both rules active created a conflict; the first rule allowed forwarding while the second one blocked it since those additional addresses weren't included. We've disabled the second rule now, but I'm stuck trying to figure out how to run two rules concurrently without removing any of the existing addresses from the first rule. Any ideas on how to resolve this issue?
2 Answers
You might want to consider using a mail-enabled security group. If set up correctly, it evaluates the group's membership rather than sending emails to the group itself. This way, you could manage incoming and outgoing email rules effectively. Also, creating multiple rules to add a custom header might simplify the process for you, so forwarding can be based on that header instead.
What if you create a distribution list (DL) that includes all the necessary email addresses? You could hide the DL and restrict who can send to it so that it doesn't accept unintended incoming emails. The transport rule would then check the DL membership to allow external forwarding, making it easier to add or remove accounts later.

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