Can I have Outlook send an Out of Office message every time a message is received; even to the same sender multiple times?
No, and you wouldn’t want to. If they send a message to you and your out-of-office autoresponds and maybe they have an autoresponder too then their autoresponder will respond to your autoresponse. Then your out-of-office will send again and their autoresponder will autorespond again and your out-of-office will….and pretty soon your mailbox (and theirs) is filling up with autoresponses and both servers are bogged down under this silly game of e-mail tennis. That’s called a mail loop and it’s bad. If you really insist upon having an autoresponder that replies every time use the Rules Wizard instead of Out-of-Office but I strongly advise against it.
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