Truck kicked itself out of gear and can't leave neutral

Hello hope someone could possibly explain this, i bought this 08 tundra 5.7 v8 4x4 does have towing package. Problem #1, not often but more so on cold starts in winter, on first Start up sometimes if I'm not watching for the first 30 seconds, there's been a few times where it'll kick it self out of park I to neutral. Not very consistently but iv noticed that either turning off the truck and turning it back on fixes it or if i turn on 4 hi and back to 2 wheel drive itll fix it. Hasn't done that specifically In a year or so, #2 I was doing some work up in west Jefferson, so at this point truck has been warmed up and drove over a couple hours, I went to back out of someone driveway with ice on it and as I'm backing out of the driveway onto a gravel side road it kicked itself out of gear again, I turned it off and back on problem resolved, #3 (this time) I was towing my trailer which I made out of an old pop up camper.it has a lighter load then most of the towing I do just some house junk like old chairs Lil bit of roofing with shingles from small shed I took down and odds and ends. I drove there bout 40 min away, and was on my way home bout half way 20 min, I took a turn which was going up a pretty steep hill i noticed it was in limp mode so I pulled over when I got to the top of the hill on the side of the road and put it in park and as soon as I did that it just kicked it self of of gear,it'll change I watched the gear selector on the side of the tranny move but won't go into any gear it's just free spinning, when I go to put in back in park it nake a terrible grinding noise but it's not in park when when the truck is off it's still in neutral. Anyone had this happen before? Just a FYI any time I haul or tow something I always use tow mode.

 

Couple updates, iv tried to engage 4x4 and it's not doing anything, transmission is full looks a Lil dark but not glittery, it starts fine and revs up fine.

 

When you say it’s in neutral, are you saying the transmission is in neutral? Or does it seem more like the transfer case is what’s in neutral. You described 4x4 operation problems as well, sounds like transfer case may be the problem.

 

I'd say transmission but I'm not 100% sure like right now the truck is off and it's in neutral I can go out their and pull or push my truck and it'll still free roll. I also read something about it could be stuck in between 2 wheel drive and 4 hi but saw something saying it just needs to be rolled for it to catch again and it's not doing that it's only rolling even when I have the gear selector in park

 

That would be transfer case

 

Well any idea on where a good starting point would be to start at? What would you try first? I don't normally work on that type of stuff, I do like fluid changes and brake pads and rotors replace airpumps and stuff I don't do the mechanical part of it iv done seals and stuff

 

Well, step one would be check the fluid level. When did you last drain and refill the transfer case? It’s due every 30-60k depending on usage. Next up would be the actuator. Determining whether the actuator is in the appropriate position, or working at all. Then, probably pulling the T-case to inspect the internals.

 

As @KNABORES stated lookbover the actuator rod on the transfer case.
Although not the same but on certain 07/08 Tundras the actuator rod would disengage. You'd have to roll the truck forward/reverse and it would engage again. Definitely check out the transfer case.