Smart Mail Groups not working after Catalina installation (multiple machines)

OK, there is hope! Here is a work around which will get you going until Apple fixes this problem properly.

Create a new Group and copy all the cards from your Smart Group to the new Group. Then add the new Group to the BCC on your email. It works. Simply select all of your Smart Group email names (e.g. select the top one then hold the shift key down and select the last one) then slide these selected cards into your new Group with your mouse. This will make the new Group match your Smart Group. It seems that Groups are working properly but Smart Groups are not. This is not overly time consuming. Good luck everyone. . . . Earle

Good afternoon jimn0842,

Welcome to the Apple Support Communities!

I understand you are having issues with the Smart Group feature on your Mac, including the new macOS Catalina 10.15. Try testing this feature in a new user account by adding a few new "test" contacts and a new smart group with different criteria than you have chosen in the past. Let us know if the issue persists in this new user account.

How to test an issue in another user account on your Mac

Contacts User Guide - macOS Catalina 10.15 - Create Smart Groups in Contacts on Mac

Take care.

Update:

In my case, problem 1 appears to be related to the use of a comma in the name of my Smart Group. This previously worked prior to Catalina. Removing the comma fixed that problem.

Problem 2 remains an issue for me.

Same issue here.

I found a "workaround". Go to the Apple Contacts application, select the Smart Group, right click, choose "Send Email to" and a fresh new email will open in Mail App.

It is not too bad for new messages, but it is a pain if you are trying to forward or add the group as a BCC on a previous email :(

New MacBook Pro, fresh install of Catalina and I cannot get smart groups to work either. Group folder identified when composing e-mail but no contacts appear. Only work around is to set up normal group and enter contacts manually which does work

Similar issue here. Catalina is a installed over a newly formatted disk - so all clean.

I can go to contacts, click on smart group and send email to group, however in email composer if I enter smart group name in To or Cc and hit enter it just displays selection for group name again - it doesn't accept group nor expand.

Manual groups work as expected

I'm also having the same problem. Mailing Smart Groups is broken after Catalina update! I have tried to recreate but still no joy.

1. While the group contains the correct contacts, selecting "Send e-mail to <Smart Group>" is erratic but always wrong. For some groups it generates an e-mail with a seemingly random set of addresses (some of whom are deleted contacts). For others it generates an e-mail with only the group name;
2. If selecting a group when creating the address list in an e-mail, the addressees are not expanded. In some cases Mail it does not recognise the group at all. In other cases it does and sends the mail. However, given the problem outlined in 1, I no longer trust the correct addressees to be mailed.

Please can you advise when this will be fixed as I have no easy workaround.

Thank you.

I have been using smart groups for years. It has now stopped working. When I enter a smart group in the bcc field it displays the group name and gives you a selection of the same smart group. you cannot enter anything else...this is ridicules.

I depend on the stuff working and just paid over 10k for 2 macbook pro's . do you guys ever regression test? do you consider these severity1? or do expect us to spend hours each day working around your mess.

I just wonder when Apple will quit messing things up in the name of "improvement"..... Hey Apple..... IT WAS WORKING FINE BEFORE CATALINA. Just use the old version of mail in the new operating system....much like use the OLD VERSION of ITUNES where everything was in ONE PLACE and easier to use..... Getting "fancy" only breaks things that don't need breaking.

This is a new problem for me since installing Catalina. In mail I send it to myself and BCC several smart groups normally. After Catalina I only see the name of the smart group and cannot expand it or add another smart group. This is very impactful for me so I do need a solution from Apple on this, and quickly. It is now Feb. 29 and this seems to have been a problem since October!!

I've created a new smart group, but like the old ones, Mail doesn't pick it up anymore. This problem has occurred only since upgrading to Catalina a couple of days ago.

Anything else I should try?

I am having the same issue with Smart Groups since upgrading to Catalina. I've tried everything recommended in the replies and nothing has fixed the issue.

I am having the same issue with Smart Groups since upgrading to Catalina. I've tried everything recommended in the replies and nothing has fixed the issue.

Is there a Fix for this matter?