Okay, so my third flight where my internet died. But this one it might be because I restarted my phone? And given that phones now (iOS and Android) use dynamic MAC addresses, it may be that my Pixel is resetting MAC address each time I reboot. Anyhow, this time my phone rebooted because I was leaning on it and it must've held the power button for a long time causing a reboot. When I reconnected I noticed my internet was out and it required me to either purchase or try T-Mobile authentication again. T-Mobile failed saying my number was in use.

As a result I tried the usual trick of purchasing with miles for the rest of the flight. Low and behold I actually get a receipt this time and in my Activity section I see a -1000 mile deduction. So whatever happened my last 2 flights where it didn't deduct miles, that was nice but this time I'm going to ask 1K Voice for the 1000 miles back.

I'm not sure if MAC randomization is reset when you reboot, and I feel it shouldn't, but this time I couldn't be sure if it was because the network was reset or not. It was a long TPAC flight where I slept a solid 6 hours and a lot can happen then.