I have triple- and quadruple-checked...and yes, I have the option set to automatically go into Car Mode when docked. I have found myself pushing the phone down rather "hard," to ensure it connects "all the way." But yea, this is a very annoying little glitch. Last week, I found myself playing with it waaaaay too much, as far as taking it out and putting it back in to see if it would go into Car Mode. 1) This is dangerous, and I probably shouldn't be doing that much while driving. 2) In some instances, by the time I got it to dock automatically, I was just a block or two from where I was going. SMH...
I know you can always start car mode manually, but it's so inconvenient. If you weren't aware already, when car mode works automatically, it automatically turns on bluetooth and connects to my bluetooth headset for any calls, and to my HTC Car StereoClip and resumes playing the last music or radio station. And when you take it out of the dock, it turns off bluetooth and disconnects from your devices...saving you time and just making things more intuitive.