I use different email accounts to manage my business vs. family and friends vs. other "buckets" in my life. Many of my clients do the same.

For those of us who use Gmail, the "sticky wicket" is when we are in a hurry and just let Gmail auto-complete the "To" address from the top of its preview list.

Is there a way to get a prompt or some kind of reminder when there is more than one address to choose among for a specific person?


I assume this is a Gmail function, but maybe it's tied to the browser or the operating system? (I'm using Chrome and Windows 10). My interest is in the "To" fields for email addresses; i.e., To, CC, and BCC (not the Subject or email message fields).

  • "different email accounts" - different gmail/google accounts? And the "more than one address" are scattered among the address books of these different accounts? – MrWhite Jun 5 '16 at 10:39
  • @w3dk - I don't know if you are asking for clarification of my question or suggesting a solution. – RJo Jun 7 '16 at 18:14
  • For clarification. What is the significance of the "different email accounts" statement in your opening sentence - how does this relate to your question? Are you suggesting that you have multiple address books spread across these different (Google?) accounts? – MrWhite Jun 7 '16 at 22:52
  • The different accounts are relevant because that's how >1 address for a person ends up in an account you don't want to see it in. Suppose we both have a work and a home account, and we agree to exchange emails using the appropriate accounts (work-related or home-related). One day you forget and email me from your home to my work account. Now when I send email to you from my work, gmail will pop up both of your addresses when I type in the "To" field, and (for some reason) your home address is listed first and mistakenly pick it first. "Which address?" prompt would help prevent the problem. – RJo Jun 8 '16 at 21:40

It seems to me Gmail already offers a "Which address?" prompt because as long as there is ambiguity it will show the options:

WA93479 example

Indicating what it would default to (with shading) seems helpful as that is the one that would autocomplete (with Enter). Given that you have presumably chosen not to autoreply (because that would go to the 'wrong' address) the pop up showing the choice would be sufficient warning for me, as a rare sight. If the automatically chosen selection is not correct, just click on an/the other.

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