MacBook Messages notifications say 'Maybe' in front of known contact names, and Messages also removes contact profile pictures, asking to update to a new picture.

samhangster, 

Let’s check a couple things, as we’d like to verify if the iCloud sync process is hung up somewhere along the way. 

If you add a contact on your Mac, does it reflect on the iCloud website? Does it reflect on your iPhone? How about vice versa, adding a contact to your iPhone does it appear on the iCloud website and also on your Mac? 

Once you’ve tested that, we’d like to have you create an export of your Contacts so a copy of them is saved in a file on your Mac. Then quit the Messages app and Contacts app. In System Preferences > Apple ID > iCloud uncheck Contacts. Once you’ve unchecked them, check them again. If at any point you’re asked to Merge the contacts, do that. Then let’s test things again. 

Here’s how to export a copy of your Contacts on your Mac: Archive or make copies of the information you store in iCloud

Thank you.

samhangster, 

Thanks for going through those steps. In the Contacts app, is the formatting for your contact phone numbers correct? For example, in the US the formatting would be (123) 456-7890 or +1 (123) 456-7890. Is the region for your Mac correct? That is in System Preferences > Language and Region.

If those both check out, are you able to delete one of the threads with a contact, it might even possible to check this with a thread to and from yourself it that shows up with ‘Maybe’ and no image as well. Then start a new thread from your Mac. 

Thanks.

samhangster,

From here, we’d like to determine if the situation is specific to your user account or if what’s happening is happening system-wide on your Mac. To do that, we’re going to ask you to create a test admin user, log in to that user, set up your Apple ID there and Messages, then test sending and receiving a couple messages. Set up users, guests, and groups on Mac

You can also reach out to Apple Support using the following link, if you’d like to work with them directly. Apple Get Support

Greetings samhangster, 

We understand that on your Mac your notifications show your contact’s names as ‘Maybe’. Additionally, when accepting the photo your contact has set on their end to share it is removed from the Contacts app only to re-appear and ask you to accept it again. 

Have you already quit and relaunched the Messages app and if it persists, restarted your Mac? If not, please do that now. 

Are you syncing your Contacts with iCloud? Do you use these contacts on any other devices and if so, are you encountering a similar issue? 

Thanks.