My consistent problem with the DL app for iPhone is a bit different. I updated to the latest version of the app each time. On 5 of the last 6 flights, I have changed seats at T-24 hours (at check in, as a Silver Medallion) to switch to economy comfort seats.
The switch has worked each time, but in those 5 cases, the App continued to show the OLD seat every time I opened up the boarding pass link. This still happened after rebooting the app multiple times, and even the following day.
I could still print out a boarding pass (from my computer) with the correct new seat, and could likewise do that at the DL airport kiosk, but the DL app boarding pass was never updated to the correct seat.
Am I alone with this quirk?