O2 Tundra - cross threaded Transmission drain bolt - leak

Purchased a 1 owner 02 Tundra 2wd Access cab about a 6 weeks ago and going through everything!!
My last item before winter was a transmission drain and fill - relatively simple!
It was my last item because I notice the radiator had some seepage and when doing a distilled water drain (petcock) and fill numerous times that this radiator was done!
So the transmission puts fluid into the bottom of the radiator and you really don't want to take a chance here from what I've read on this site!! RockAuto had a new one delivered in 2 days (Denso) and only cost 140.00 approximately... I might actually replace it every timing belt change!
So 2 days ago I put a new radiator and lower/upper hoses and new thermostat and rad cap.... then started filling while draining my transmission.... noticed the bolt didn't really break free as a bolt should... told my friend who stopped by after work... I think this bolt was crossed threaded... and sure enough after we fished it out of the drain fluid with a magnet... lol noticed the damage!

Side profile should have 5 threads and this literally had 3, so threads 2 and 4 were totally missing and shiny... I put it back together and gingerly put some turns on it and it tightened ever so slightly and loosened and I went a bit more until it snugged...
Guess I could have used a dab of gasket sealer? but I wanted a true analysis of the situation! I will take this into the back country of Idaho (camping) where shops aren't a luxury!
I remember breaking a window in a Camry to get home once on a trip around Stanley and Redfish Lake... lol no joke! I did have a cell signal and sourced the small triangle window on eBay and bought it before I broke the window.... took a minute to fish out all the glass in the back seat... 04 Camry Le. Great car for work commute!

So yesterday and today I've noticed tranny fluid leaking.... want to let the new fluid's detergent do its job before I drain it again... so far I've lost maybe 4-6 oz. and the fluid I drained did have a good color to it... no pic of anything on this... daylight was burning and I want to grab dinner with this friend.
So I ordered a new bolt and washer and picked them up at Toyo and also grabbed a tap and die set at Horrible Freight. Hopefully I won't need to open it up so I can return it...

My thoughts are that the bolt is absolutely trashed but I'm hoping the pan is in good shape... did the engineers make the bolt from milder material?? that is my assumption!
So when the time comes to open this back up, I hope I can start the new bolt by hand and get it all the way into the pan just using my fingers while checking for slop. Of course I will do a visual inspection of the pan threads to make sure they are all there!!
If all goes well and I don't have to retap the pan threads? I will torque down the bolt to specs... and call it good... I may even put a dab of gasket sealer at the base of the bolt and washer?
My goal is to have confidence in the finished product and not drop another 220 dollars for a new pan at the dealership, I might consider a jalopy jungle option but according to looking up the pan at the dealership there are 5 different models for this particular year! So if your chasing parts? make sure you have some detailed pics handy to identify your pan.

I'm very/fairly confident I don't need a new pan....
I started this discussion 2 days ago and a reply was given me and telling me to put this out there for the journey for others.... and also this guy posted numerous options on fixing... one of the best is weld a nut on the pan and go from there... never really considered it but rather genius!! nut could be inside or on the bottom.... not sure what inside clearance is?? Probably the better option if offroading is your forte?

 

I wouldn’t attempt to replace the bolt without tapping the pan threads first. Just be gentle and take your time. Unless it is completely fubar’ed, you should be good.

 

This! At the very least you should chase the threads in the pan

 

Use a shop vac and nozzle to pull chips away while chasing.

 

I would agree with your steps and add a note:

Option 1: Try and tap it if you feel comfortable. ( I need peace of mind so I would have to feel ultra comfortable that the tap size is accurate to the drain bolt)
Option 2. If you have the money I would just order a new pan and replace it along with the filter while you are at it. Replacing the filter is just as important in my view if you are going to change the oil. Unless you have documentation the filter was recently changed.

 

Okay, got it taken care of today.... the pan threads actually looked really good, so I attempted to hand thread. I didn't force it and it just seemed to not want to take! So I busted out the Horrible Freight 20 dollar metric set and found appropriate size matching the new bolt. Only went in about maybe 2 1/2 turns doing a quarter turn and back out an 1/8 as I went.. until I felt it really starting to cut. then backed it all the way out... still had some fluid running out, so that should of flushed any metal debris. Did notice a few flakes as I transferred from my drop pan to my waste container.
Started the new bolt and it was still snug, but it went in and I feel I have a really really good seal. I'll wait until next change out to see how successful it was?

here is a pic of the bolt! It did sustain more damage than I had previously noted...

I would like to mention when I wanted to run it low... it was moving it down to the add line not running the transmission dry.
Language is interesting... lol. in German there are like 5 or 6 different words for cylinder depending on the variety of cyclinder.... and still fascinating that they can't build a vehicle with the longevity of Japanese. lol I'm mostly German so I can get away with the trash talk!!

Thanks for the help gang!!!!!!!

 

How many ugga duggas did you throw at it?

 

Wow. Definitely stripped. Glad it worked out for you. Lets hope it holds!

 

Yeah that bolt is definitely fubar’ed. Sounds like you got a good bite. Dont be scared to tap the threads on the pan. It will always give you a pucker moment but I have had very good success with them. As long as you have the right size and pitch you are good. It’s take your time and follow the directions - start the thread, chase it about a quarter turn, back it out and repeat. Then start the bolt and thread properly - torque to spec.

 

I didn't want to use the tap because I wanted to return the set... not scared to use a tool. Just common sense and let the tool pull itself through the hole. Grew up on a farm... I wouldn't be intimidated welding a nut on the bottom of the pan either. lol Maybe the next go around...

The bolts are definitely softer material than the pan.... good thing!