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Should I be worried that my car's tracking has "gone dark" en route?

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It's possible the car is in a covered transport that is blocking gps reception but not data. Give your car the Tesla Delivery Checklist inspection at delivery to make sure all is fine and harass them often since they're so late, but don't panic.
 
Whoops, ignore me then!
No way! It was a helpful suggestion. I forwarded it to the dealer who asked Tesla if that was a possibility. The (filtered) response was that it was only possible in two scenarios:

1) The trucker is a skilled hacker (read: can follow a Youtube how-to) and put it into dev mode.
2) The previous owner had it in dev mode and the trucker inadvertently found transport mode and engaged it.

They couldn't confirm it, however, because in its current state they can only get limited information. So it wasn't ruled out!

They say I'll have to wait until it arrives and do a reset. Just really odd timing that something "so rare" happens just as its being picked up.

The good news is, the trucking company contacted me today saying they're on schedule and I should have it Friday! YAY!
 
Yeah well, I was trying to appreciate your contribution anyway :)

FYI, the car is still reporting its estimated range (which keeps declining) but it still isn't reporting its location. Instead of saying it is at the dealership, however, it now shows a black screen with "communication error" in small text at the bottom.