Tesla WiFi issues with 2019.40

When we got back from our trip to Puerto Rico my Model X Pensive had an update available, but since Tesla has started requiring WiFi to receive updates I appear to be stuck with 2019.40.2.1. I eventually downloaded V10 over weak public WiFi connections the car intermittently connected to while it was parked, and fetched the most recent update using my mobile phone as a hotspot, but under the current version, two different symptoms are each blocking those routes.

Wi-Fi keeps turning off

The V10 update eventually was able to pull the download because it intermittently had a strong enough signal to open WiFi while parked. Under 2019.40.2.1, however, WiFi turns-off every time the car goes into park. It stays off until you manually turn it back on. Oddly, when you open the information dialogue, the opposite behaviour is described where WiFi should turn on automatically.

Wi-Fi is Turned Off

Wi-Fi can be turned-on manually, but it turns off each time the car starts, despite this message.

Updater doesn't realize when it's on WiFi

Even if the WiFi were to stay-on, when I've connected the device to a hotspot, even when services like the Web browser work, the software update section does not seem to notice and continues to suggest connecting to WiFi. In past versions of the software, it has take several minutes for the car to recognize the change, but even after hour long car rides, no progress is being made with the download.

With those two issues, I may need to wait until my next annual service appointment to see newer software. Fortunately, despite some odd stopping and notably poor vision for AutoPilot, unlike under 2019.36 software 2019.40 doesn't completely shut-off AutoPilot when faced with bright sunlight which makes highway driving during sunrise and sunset traffic more manageable.

Update available

Even when connected to WiFi, the updater doesn't start downloading.