Smart Lists not Working in Mail

I don't think it has anything to do with gmail but I do think something got screwed up in the latest OS update to 14.0. I updated to 14.0 last week. I have been sending weekly smart list emails for the last 4 weeks and they have always correctly listed only the smart list name in the "To" field. But just today, the 1st time I have attempted to send emails to these same smart lists, all of the actual email addresses now show up in the "To" field instead of only the smart list name. The box for "when sending to a group show all member addresses" in my mail settings is NOT checked (and never has been checked). Again, this function worked perfectly until I updated to 14.0 Hello? Hello? Anyone at Apple on this?

apple mail - unable to send mail using smart list, have created smart list, NO drop down box option to send email,

Sonoma 14

Hey AK Mike,

Thanks for using Apple Support Communities. This might be due to your Mac Mail Composing settings. You can change those settings using guidance from Change Composing settings in Mail on Mac - Apple Support.

"To change these settings in the Mail app on your Mac, choose Mail > Settings, then click Composing."

"When sending to a group, show all member addresses"

You might also find Email a list or Smart List in Contacts on Mac - Apple Support helpful, the following in particular.

"In the Contacts app on your Mac, do any of the following:

• Control-click a list or Smart List in the sidebar, then choose Send Email. 
• A new email opens in the Mail app, addressed to the list or Smart List.
• Drag a list or Smart List from the sidebar to an address field in an email you’re writing.
• In your email, either the list name or individual contact names are shown, depending on how Composing settings are set in Mail.
• If the list name is shown but you want to see the individual contact names instead, click the arrow next to the list name, then choose Expand Group."

Take care.

That's how it's supposed to work. Just the List name appears in the To or BBC field.

Here's some food for thought: it's good computer etiquette to use the BBC field when sending to multiple recipients so that you're not broadcasting each recipients' email address to all of the recipients. When using the BBC field each recipient only sees their name and address in a group message and no others.

When you place the cursor on the list name, you should have a little down arrow - that’s a menu, and one of the items there is Expand Group, which should replace the name of the list with the addressess. Don’t you see that?

If you send a single email do you get the same warning sign? It's probably not the Contact Group but a problem with the internet connection to the servers. I got the same thing a couple of days ago with single emails. A Safe Mode boot got me back up again.

Have you installed and run any "cleaning", "optimizing", "speed-up", anti-virus or VPN apps on your Mac?

I've never seen a smart list from Contacts listed in the dropdown menu. The dropdown menu doesn't show until you start entering in the To/BCC field. Then all that shows are contact starting with the first (and then the second, third, etc) letter typed. When I use a smart list I just start typing in the smart list name and it's there.

I always use the BBC field with smart lists (except for family members) as I don't want to publicize recipients email addresses to others.

I am experiencing a similar occurrence. I am having to right-click the smart list in contacts and select "send email to <smartlistname>". This places the emails addresses directly in the "To" field. I then have to highlight the list in the "To" field and Cut and Paste them into the "Bcc" field. Ridiculous. I've wondered if it is because my contacts are synced from gmail as I had to move them there so my husband and I (we work together) can share our full contacts list. When we've done this through Apple, toggling on "Contacts" in a shared email, it prioritizes that email info over our user name (AppleID) user content. All the functionality is there, but the programmers don't listen to users. Solving one problem leads to another somewhere else down the road...

Have you tried deleting the smart list, recreating it and send an email with it?