1. Check Mail Composing Settings
The way your Mac Mail displays group addresses (like a Smart List) is controlled by a setting in Mail's preferences.
Open Mail.
- Go to the Mail menu and choose Settings (or Preferences depending on your macOS version).
- Click on the Composing tab.
- Look for the setting: When sending to a group, show all member addresses.
- Check this option: If it's unchecked, try checking it. Some users report that checking this option makes Smart Lists work correctly by forcing Mail to use the individual addresses.
- Uncheck this option: If it's checked, the email will show all the individual addresses instead of the Smart List name. You can uncheck it if you want only the list name to appear (though this is where the issue often arises with Smart Lists)
Verify Smart List Functionality
- Test with a regular List: Try creating a regular List (not a Smart List) in the Contacts app and manually adding a few contacts. See if you can use the name of this regular list in the Mail app's "To" field. If the regular list works, it may indicate a specific issue with how Mail is handling the dynamic nature of the Smart List.
3. Expand the Group Name (If it appears)
If you type the name of the Smart List in the "To," "Cc," or "Bcc" field of a new email, and the list name appears but not the individual addresses:
- Look for an arrow: Place your cursor on the list name in the address field. A small down arrow should appear next to the list name.
- Expand Group: Click the arrow and select Expand Group. This should replace the list name with all the individual email addresses.
