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I have a contact with two email address: a personal and a business account. I email him regularly at both depending upon the subject.

Occasionally I send an email to his personal account while including other people at his business account, by complete accident.

How can I setup Gmail to stop me from emailing his personal account when there are other contacts included that are from his business domain?

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3 Answers 3

I think the combination of two lab features might just do the trick for you (explenation from Google):

  • Undo Send: Oops, hit "Send" too soon? Stop messages from being sent for a few seconds after hitting the send button.
  • Got the wrong Bob?: Doh, have you ever addressed an email too quickly, and included Bob (your boss) instead of Bob (your friend) by accident? If you're emailing more than two people at once, Gmail will check if you meant to include Bob Smith rather than Bob Jones based on the groups of people you email most often.
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1  
+1 "Got the wrong Bob" was exactly what occurred to me after reading the question. –  GAThrawn Nov 5 '10 at 15:29
    
I have "Got the wrong Bob" on, didn't do Jack. –  Jason Nov 5 '10 at 15:41

I would set him up with two separate Google Contacts.

John Doe (Work) John Doe (Home)

A pain in the neck to have two contact records for the same person, but it would be much less likely that you'd confuse them.

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I don't use GMail, but to eliminate this problem, I use groups in Bigfoot, Juno and Eudora. I'm making an assumption that GMail has groups capability.

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