Messages app not sending images or group messages on Pixel 8 Pro after last update

It would be very unusual but an update could possibly change your APN settings. Some carriers may expect some Google magic to keep services up to date, especially for MMS where technology still evolves (and some carriers even drop the service). You might check some apn threads to see if this might be your case. Note how the https entry is required correct for MMS.

If indeed an e-2.9 issue perhaps best recorded in feedback thread Feedback for v2.9