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I have my own personal mail account (a gmail account) and my academic email account (a university account) as different profiles on my Mail application in OS X Snow Leopard. I sometimes forget to switch the outgoing account to my university account when emailing my students and it will send from my gmail account instead. This is not a huge deal but I would prefer to have my students never get mail from my gmail account.

Is there a way to have Mail warn you when sending to a certain address (or an address that has a certain keyward in it?)

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up vote 2 down vote accepted

Yes, you can have Mail put certain addresses in the to field in black and all others in red.
I use this to have Mail flag email that's going outside my organization.

Do this by going to Preferences > Composing.
Then under the "Addressing" header check "Mark addresses not ending with [ ]." Inside the box put "".
Then every email address destined within your school will be black, and all others will be red.
Just the thing to ensure FERPA compliance.

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interesting feature, but if i understand it correctly, it is not what i am asking for. no matter which email address i send it from, @<myschool>.edu is red. i am hoping for something to show up ONLY if i am mailing to @<myschool>.edu but i am mailing it from my gmail account. as it stands, there is still no way to be alerted if i am mailing from my gmail account or my school account when i am mailing TO a school account. – drjrm3 Sep 2 '12 at 18:46
Well, your from: address will be RED if it is gmail and BLACK if it is @<yourschool>.edu. – vy32 Sep 3 '12 at 0:04
Not sure why I never accepted this answer - better late than never right =) – drjrm3 Feb 19 '15 at 21:07
Thanks for finding accepting, @Laurbert515. – vy32 Feb 20 '15 at 21:38

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