Did winter tire swap - TPMS issues

I tried doing a search but didn't come up with an answer for this one. I have a 22 Pinnacle Hybrid. On Monday I had a new set of winter tires/rims installed. I bought the recommended TPMS sensors as advised by Costco Tire Centre. (DILL brand I believe). When I drove away from the tire shop the new TPMS sensors seemed to have registered with the vehicle as they showed tire pressures on all 4 wheels.

Yesterday I drove to work with no issues whatsoever. When I left work I started the van and immediately got a warning message on the dash that said "Service Tire Pressure System". The tire light was blinking and eventually turned solid yellow. The tire pressure screen showed "--" at each wheel. I drove around for a while and even made some stops and each time I started up the van the same warnings flashed.

Later on yesterday evening, I started the van and the warnings did not come up and there was nothing in the Messages screen. However the tire pressure at each wheel still shows "--" and it says "Tire pressure unavailable" at the bottom.

I've driven a lot of Chrysler vehicles and done the same wheels swaps and it's always relearned the new sensors within minutes. I've never seen this elaborate of a progression. It's also weird it keeps changing.

Any idea what could be going on here? Is this something I should take back to the tire shop or is this one of those things where they made it so you have to get the dealer to reset the van every time you swap tires?