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I am helping someone with administrative duties, and they very frequently have to send emails to the exact same 2 email addresses.

The two email addresses are extremely similar, and I have to double check each time to make sure I get both right.

In the recent days, I have created a macOS text clipping with the two addresses that I simply open, copy and then paste in the "to:" field of Gmail.

Example: I add "johndoe@gmail.com" and "janedoe@gmail.com" to a group that I call "John & Jane Doe" and whenever I want to writer to them both I just have to write "John & Jane Doe" and Gmail does the rest.

We are using the email client in Safari, no third party app.

Is there a simpler way to add two email addresses to the "To:" field without having to search for them in the Address book, especially when the Address book contains similar sounding addresses that can lead to confusion?

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    Gmail uses Type Ahead. Are the email addresses different in the first 2 or 3 characters? – John Apr 10 at 1:49
  • I'd have to check. But ideally I'd add both addresses in one go – MicroMachine Apr 10 at 2:07
  • That seems a bit hard. I just type ahead because it prevents your issue. – John Apr 10 at 2:10
  • But what if the difference between the email addresses is after the “@“ or after the “.”? How foes one avoid mistakes? – MicroMachine Apr 10 at 3:14
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    @MicroMachine - how about using a label to create a contact group? support.google.com/a/users/answer/9310148?hl=en – Mr R Apr 10 at 4:14
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This approach requires that you setup your Mac to make the web-based Gmail your default Mail "handler". Follow the steps here first: https://www.cloudwards.net/how-to-make-gmail-your-default-email-client/

Then, open Safari (easier for this next step) and type a mail URL into the address bar but do NOT hit return. Enter you email addresses in place of the fake emails shown here, but use the rest of the format of this:

mailto:fake@foo.com,faker@food.com

Then, "drag" that URL from Safari's address bar to your Desktop (or any folder). Double click on that new "mailto" shortcut and you will open your browser and Gmail and start a new message to the addresses that you entered when you made the shortcut.

This is simple to use, but it's not flexible. Besides requiring that you change your default mail handler, you would need to repeat the process if you wanted to add/change any of the email addresses.

The excellent suggestion by "Mr R" in the comments about using a Gmail label or group would be easier, but this is something you could setup on YOUR Mac and share to the admin that you are helping, without direct access to their Gmail.

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  • That’s a really cool idea! I didn’t even know you could have a different behavior than the mac Mail app opening everytime you click a mailto link, just that in itself is great! – MicroMachine Apr 12 at 13:58

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