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Message: Drive Button Problem Vehicle May Not Be Able to Enter Drive

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This normally means that the button is not working properly or the gear selector board is going bad. Most likely the button has failed. The message is the same if the button is held down for too long since the car thinks that the button has been stuck in the down position.
 
I'm not sure whether I got that exact message, but I do sometimes have trouble getting out of park. It's all about the timing between inserting the key and changing gears.

I have found that once the car gets confused about leaving Park for Drive, it simply will not work. I have to physically remove the key and start over. Now that I've experienced this a few times and tried everything I could think of with the brake pedal and emergency brake, I've decided that it's fastest to just remove the key and try again from the beginning.

I realize that this does not bode well for a firmware fix, because my behavior works around the flaw and thus I won't be able to reproduce it for Tesla engineers to see. In some respects, I suppose I should try to write a script for how to reproduce this confusion in the Roadster 2.5 and then hand over my notes to Tesla. I'm sure they could fix what I'm seeing if they tried.
 
I agree. Especially the reverse camera.
... a fair complaint, but this particular behavior is entirely out of Tesla Motors' control. The Alpine head unit has a direct wire to the reverse signal, a direct connection to the camera, and its own power supply and presumably ignition input. The speed of the display is entirely Alpine's design (flaw).

The best Tesla Motors could possibly do is search for another double-DIN unit with remote video input and automatic reverse camera switching that is faster - but you could do that yourself (if you car is in warranty, you might not want to alter the radio, but otherwise you're free to install anything that competes with the Alpine system and does a better job).
 
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I used to constantly get the "reverse button failure warning" when backing out of my garage. The latest firmware made that problem go away. When I would get the error, the car would actually be in reverse and everything worked fine... I'd just get the warning message. So do you have the latest firmware?