Personalised group email

I need to send a farewell email to each of my students in a class we have just completed. There are 22 students.

Most of the text will be common. However, my institution wants the email to be addressed and sent to each student individually rather than using the “group” email in which the one email goes to all students without individual addressing. The institution would also like me to include a personalised greeting - e.g. “Dear [student name] in the body of the email. (It is the only text that will change.)

I have Apple - using Mojave and Outlook.

I have explored using the Outlook / Word mail merge function but, when I get to the Finish & Merge step, the option for Merge to Email is grayed out, so the option is just to create / print individual Word documents.

I am wondering if there is some sort of “bulk email” solution with one or other of these apps, or some cheap way, I can send individual emails rather than having to copy and paste the text 22 times into individual emails, and address all 22 individually?

There’s a mail merge solution here that utilises Pages, so hopefully you have that available to you:

I’ve not used it myself, but I’m pretty sure the author has a good Mac automation reputation :wink:

If this isn’t something you will repeat often, I’d perhaps be tempted to go for a bit of manual copying and pasting, it would probably be a little faster to do for such a small set of recipients. I’ve had to deal with mail merges a lot in the past in some former jobs, and they often need a bit of bedding in and hand holding efforts to get working just right. But if you do see yourself re-using this in the future, it would be worth investing the time now to try this out.

Saying that what I’d actually more likely do is take a middle ground. Have a list of the student names and e-mail addresses in a spreadsheet or text file, and have Keyboard Maestro quickly switch between them to do the copying and pasting for me. Maybe even utilising a Keyboard Maestro or TextExpander snippet to put the mail content in.

If you do want to do any sort of automation, I’d recommend doing it offline so the mails are queued up and can be checked before they just get sent out.

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I was starting to reach the same conclusion that cutting and pasting would be faster.

As I had the email addresses and the student names in a spreadsheet table, I did a bit more exploring.

It turned out the Word Outlook method required me to change my default email client on the Mac to Outlook, restart Word and then the Merge to Email function was there.

A couple of confusing dialog boxes along the way but, in the end, an email went out to each student with their own personal greeting. Objective achieved!

Thanks once again.

Randy Singer on the MILO listserv pointed out an interesting service which is free for up to 150 emails a month completely free, no sign-up required. Direct Mail for Mac

If you go into the settings of the macOS Mail app you Can set the default mail application. If you change this to Outlook then you can use the mail merge function in word.

Personally I don’t use outlook for the daily mail work, but I did not find any compareable mail merge functionality for macOS native mail app. Therefore I change the default application, then do the mail merge and set the default mail app back to the standard mail app.


I had a similar problem as OP and I had a hypothesis that your answer about the default mail app was the solution. Thank you for confirming that!

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