On 7 Oct 2020, at 10:10, Annamarie Pluhar wrote:

I would love it if when I’m about to send an email from this gmail address I get an alert that says something like “Do you really want to use this email?” With a yes or no I can click.

See "Custom Message Verifications" at https://manual.mailmate-app.com/hidden_preferences -- it will do exactly what you want! Copy the sample there to get the format the plist file needs to be in; then just replace the "conditions" line in the sample with

from ~ 'YOUR-GMAIL-ADDRESS';

(which means "the From: line contains YOUR-GMAIL-ADDRESS") and set the "title" and "details" lines to display whatever alert you want to be alerted with.

The easiest way to figure out how to format your conditions, if you're not fluent in whatever syntax plist files use, is to create a smart folder with the conditions you want and then inspect its definition by quitting MailMate and opening the mailboxes.plist file to see how the smart folder is defined there.

You can check for multiple conditions at a time, and have as many independent verifications as you want. I have about a dozen, ensuring that I don't send work email from my church-board address, don't send board business messages from anything *but* my church-board address, don't send personal mail to a work contact, don't fail to BCC myself or use the wrong signature (I have auto-BCC set, but if I change the sending address after I've begun composing a message the BCC or sig sometimes fails to change accordingly), don't reply to a mailing list when I mean to reply to an individual poster, etc. etc. -- the ability to set up such verifications was one of the factors that originally drew me to MailMate!

Shoshanna Green
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