2009 Dodge Grand Caravan SXT (3.8); 2003 Dodge Grand Caravan eL (3.8)
The dipstick does NOT bottom out at the bottom of the pan.On my 2014 T&C, when I insert the oil dipstick into the transmission filler tube, the dipstick bottoms out at the bottom of the transmission pan. (After sitting overnight, the level appears to be right about at the crook of the oil dipstick, when the outside temperature is about 40 degrees F.)
The dipstick that one can purchase and use according to this procedure cited above (62TE Transmission - Caravan's without Dipstick Refill - Bob Is The Oil Guy) appears to have a stop on it, such that it "bottoms out" at the top of the filler tube. (Note: this bobistheoilguy procedure is for a specific transmission, so for other transmissions the measurements in the chart are likely going to vary). From a quick look at the procedure, it looks to me like the special tool measures the true depth of the fluid in the transmission oil pan.
The dipstick does NOT have a stop that bottoms out on the top of the fill tube (but I did see on another forum where someone modified a dipstick to do that.)
The dipstick DOES bottom out on a stop at the end of the fill tube.
Here is a picture from when I change the fluid and filter: