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I use a gmail account with apple mail. It's very annoying that I have to pick a matching signature everytime I decided to change the from email alias.

Is there anything I can do that will allow me to match up a signature with each alias email address?

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For this kind of professionnal use of E-mail, I abandonned Gmail and Mail many years ago.

I use Thunderbird ( Thunderbird home page ) which is much more secure, lets you configure it exactly the way you are looking for through the concept of "identities". You can define many "identities" per account, each one being defined by:

  • a name
  • a "From:" field
  • a "Reply-To:" field
  • an "Organization:" field
  • a signature (in HTML or text)

I use this E-mail client as a much faster interface to Gmail letting me answer with the identity required and permitting my correspondant to answer me with my appropriate reply address. enter image description here

As a collateral advantage, you will most probably discover many other advanced function to use in Thunderbird.

  • Out of interest, how is it more secure? – unknowndomain Aug 15 '18 at 20:52
  • I wanted something that was completely integrated with the OS. Kinda sucks that you can get something so basic accomplished. – Frank Barcenas Aug 16 '18 at 0:05
  • Mr Smith doesn’t use more than one E-mail and one signature, when they should (buy a pizza versus candidate for a job). Sorry about this but your need is rather a professionnal one, as seen from the sausage vending machine 😉! – dan Aug 16 '18 at 9:23
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    @unknowndomain: because of the number of functions in the Preferences > Security and Preferences > Privacy settings. These are functions that are usable by beginners and advanced users. To give you 2 (from my point of vue) winning settings :[return] Privacy > ☐ Allow remote content in messages, [return]` Security > Junk > √ Enable adaptive junk filter logging. – dan Aug 16 '18 at 9:38

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