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Is there a way to replicate an email bounce / redirect using Office 365 hosted email using either the OWA web app or Microsoft Office 2016 for Mac?

Basically, some subset of emails that get sent to me need to be sent to another distribution list. I want to be able to automate sending some of my mail (but not all of it) to another address. When outlook forwards the message, it's now from me instead of from the sender which messes up replies and actions based on who sent the mail.

Eudora used to tack on "via person who redirected" to the subject line and Apple's Mail app has a Redirect menu option that is disabled when connected to Office365 mail servers so I'm guessing this might be a configuration issue or banned by Outlook entirely.

Is there any sort of rule or workaround that would enable me to redirect some messages when needed?

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You should be able to create a rule in the Outlook 2016 for the Mac. In Outlook's menu select

Tools --> Rules

Use the + button near the bottom of the pop-up to add a new rule. Give the rule a name (Shunt-Foo-List-To-Bar-List). For the condition, select something that will uniquely identify the message that needs to be bounced. This could be the To: address if messages to the list are consistently addressed to the list's address, or if the list uses a [tag] in the subject line you could match on that instead. Then under Do the following:, select Redirect To and set the address where you want it to go.

There are times I would like to be able to interactively redirect an individual message to a different address, but I've yet to find a way to do this in Mac/Outlook. But at least this works for cases you can easily identify ahead of time.

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