I sent an email to Tesla about how this feature works, here is what they said:
Hello Mr. [AmpedRealtor],
Thank you for contacting Tesla Motors Technical Support regarding your question about Hill Start Assist. This feature, which was introduced in firmware version 5.9, is intended to automatically hold the car by maintaining brake pressure when the brake pedal is released, preventing the car from rolling while the driver switches form the brake to the accelerator. Hill Start Assist will release after one second, or when the vehicle begins to accelerate. This function will engage when the car is in Drive and facing uphill, or in Reverse and facing downhill. It is always enabled when the vehicle is in Drive or Reverse and does not need to be activated by the user. The feature engages on grades of more than 4% incline/decline.
I’m not aware, nor was I able to find any information regarding how firmly the brake needs to be depressed in order to engage Hill Start Assist. I would be led to believe that the intention would be for the feature to engage whenever the brake is held, no matter the pressure. If you believe the feature is not working properly and/or would like to have a service technician “test ride” the car to see for themselves, we’d be happy to arrange for that with your local service center.
Feel free to let us know if you have any additional questions.
Best regards,
Eric