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Make sure your APN is correct. Sometime back I had issues with MMS where it would only send over wifi but not cellular and I was able to fix it by editing the APN. You can look online for the latest T-Mobile APN and compare it with yours to make sure they match, and if not edit it accordingly. Look specifically at the "MMSC" setting.
Interesting, guess it wasn't the APN but that was worth trying.
Does it happen only on your home wifi or others as well? If only at home you might have an issue with port blocking which could be an ISP thing. You could try the suggestion above to reboot your router and see if that makes any difference, if it doesn't maybe see if there are any ports you need to forward (shouldn't be but you never know) or ask your ISP if they are blocking anything. If it's happening outside your home network as well then forget about all that.