@jantinzi There are a couple of posts that talk about similar issues. I am not saying they necessarily have solutions for your specific situation, but if you read through them, you might find some useful clues:
https://community.braxtech.net/t/sms-works-fine-mms-not-so-much-on-t-mobile/1446
https://community.braxtech.net/t/text-and-mms-not-working-sim-issue/1979
Just to confirm, you are directly with T-Mobile, and not an MVNO that uses T-Mobile as their carrier, correct?
Also, can you post a screenshot of your APN settings, please?