2012 Tundra Transmission Issue

Hello,
I have an issue with my 5.7 liter Tundra leaving me scratching my head. The last two times I have launched my boat, when I put the I shift from park to drive (in tow mode) the transmission will not engage. It doesn’t matter if I shift in to reverse, park, or whatever following drive, the transmission will not engage. After repeating the process multiple times the transmission will finally engage. There are no warning lights and other than the launch ramp issue, the transmission works fine. Anyone have any ideas or insight?
Thanks

 

You back down the ramp, get the trailer in the water, then put the truck in park and let it rest against the parking pawl in the transmission. Then when trying to shift into D from P with the weight of the truck and the trailer and the boat resting on the parking pawl, it won’t release. Is that what’s happening?

 

Yes Sir

 

Good, did you recognize the likely problem in there?

 

Unfortunately I’m missing what the likely problem is. This Tundra is fairly new to me. Thanks

 

If you’re on an incline with a heavy load behind you and you put it in park and let off the brake, the weight of the vehicle is now resting on that parking pawl in the transmission. It may not be able to shift out of park with all that weight on it. Do you set the parking break when you get out?

 

I don’t set the parking brake but it sounds like I need to going forward. The first time it happened I didn’t even get out of the vehicle, just went from reverse to drive at the bottom of the ramp to pull forward a couple of feet. Thanks

 

Good habbit to get into or you're going to go bloop bloop.

 

Yeah, no doubt. Thanks for the wisdom.

 

Now. Another possibility is low transmission fluid. On an incline this problem could be exacerbated. Need to check your fluid level

 

That was actually on the top of my list of things to check but wanted to see if there was anything else I might be missing.