I do consulting with several clients who require me to speak with vendors and their clients on their behalf. As a result, I have several client-based email accounts that I work in regularly.

Occasionally, when sending a new email, I will accidentally use my primary account instead of the client's account. This is an easy oversight, but has caused some headaches for my clients.

I've tried getting creative with Outlook rules, but to no avail. I'd like to find a way to automatically add people to specific groups when they send me an email, and alert me when I attempt to send them an email from the wrong account.

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