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boot not latching properly and us not noticing was one reason we got rid of our boot sound-proofing seal. Not worth the risk. Now we have a teslafi reminder set and I'm more vigilant to check the phone to make sure it's locked if I can't see it.

Why the hell a super smart car has to beep the horn when it locks is beyond me. It's way too loud for a quiet street at night or early in the morning when a simple chime or even a lights flash would do. C'mon Elon, why not a fart noise? Oh wait...
 
A lot of people seem to say that the Bluetooth on the phone for the easy access requires the phone to be really close(eg“doesn’t work from the back pocket”) However I had to stop using it as even though the doors locked when I walked away if I left my phone charging on my bedside table I was able to open the car from about 15feet away diagonal through the window/walls every single time I tried. I also noticed the the horn doesn’t sound when you open the car this way which I find strange.
I have just disabled the feature altogether and I’m using the card key in my wallet which is honestly hardly much more effort and stops me forgetting my wallets
 
How about c) & d) ?

c) The money is there but not where you left it - its fallen through a gap and is now rattling around underneath
d) Your significant other took the car for a spin and used it for parking or just lifted it
 
If you’ve got it set for lock on walk away, and anything is left open - it just won’t lock and doesn’t notify you,

This is a real issue and compromises passive entry.

The worst case is if the car appears to lock (beeps horn, folds mirrors etc) but actually isn't locked. This shouldn't be allowed to happen.

In the case where the car doesn't signal that it is locked when you walk away but you don't notice the fact, you should be actively notified that the car is not locked if passive entry is enabled.

Does anyone know which of these cases is what actually can happen?
 
Ask and ye shall be given....

Looks like a solution - just made available in the Model S OTA update 2020.32.1 in the US

CAR LEFT OPEN NOTIFICATIONS

A mobile notification will be sent if the trunk, the front trunk, or any door is left open for over ten minutes. If all doors and trunks are locked, a notification will be sent if any window is detected to be open ten minutes after leaving the car.

To adjust which notifications get sent, tap Controls>Vehicle>Car Left Open Notifications. Notifications will not be sent when the car is at Home if "Exclude Home" is selected.