Can't enter a smart group in Mac Mail

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I wanted to write an e-mail to one smart group and copy another smart group. For some time, I've had problem in that it wouldn't show the list of people, but now I had a worse problem.

I would start typing in the smart group, and then select it from a drop down menu, but when I tried to send, it did not see a valid group. It appears that it only tried to send the label of the group.

I got around it by opening Contacts, starting a new message to that smart group, and then cutting and pasting the people into my message. (I did this twice, once for the To, and once for the CC).

I have the latest version of Catalina.

Any ideas what is happening and how to fix it?
 

Cory Cooper

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Hello,

You should only have to take the steps you listed. Once you elect the group, it should display all of the names individually, if you have Mail > Preferences... > Composing > Addressing: When sending to a group, show all member addresses checked. With that checked, and using Apple Mail as your default email application, you can also right-click on the group in the Contacts application, choose Send Email to "group name", and it will start a new email with all the members of that group showing.

C
 
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That's what I ended up doing. And since I had to do it twice in order to have both my To and CC lists, I cut and pasted the names.

But I'd like it to work the way it used to work, with me typing the name of the group and it filling the names itself. Maybe the problem has something to do with the contacts being in my wife's iCloud instead of mine.
 

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