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It's annoying to have to create a rule to move all messages from certain people to a certain folder, and then create another to move all messages to those same people to that same folder. Has anyone been able to find a work-around yet?

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No workarounds here. You can't combine inbound and outbount rules, sorry.

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Not native rule for such requirement in Outlook client. Outlook rule is also known as inbox rule. It generally auto-proceeds the incoming messages other than outgoing messages.

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