The PO f'd up the trans cooler install big time, on my truck. I didn't focus on, or notice it for a bit.
1st thing they did wrong installed upside down, so it trapped air.

Not a great picture, but as you the hose at the bottom. There is another hose on bottom left. I think this is an early B&M supper cool .
2nd thing they really f'd up is they put it right in front of the fresh air intake. Heated air straight into the carb.
Once I discovered this I made some changes.
Moved to driver side. Both internal and external coolers being used at this time. Made a difference in trans temps and preignition.
Still was getting to hot under certain conditions. Like towing the boat at low speed in town at 115°+. Not in 4th gear so not locked up. Now I can manually lock 3rd and 2nd. I do use 3rd lock up some, but I have concerns about the lock up clutch being able to handle the torque in second. All that torque converter heat was saturating my cooling system, gradual build up to over heating. So I added thermostat controlled fan.

This didn't help as much as I thought it should. When I was testing in similar circumstance, the thermostatic switch failed so no fan. I wired it hot after that.
Still concerned about torque converter heat in the cooling system, I decided to go stand alone remote cooler only. I purchased the biggest btu cooler I could find on Derale web site, excluding the high $$$$ racing ones. 13870 Hyper cool extreme, advertised at 67000 btu. I mounted under the truck towards the rear. Using -AN 6 fittings in the trans with braided hose to the rear, eliminating the rad cooler.
This work exceptionally well. Just driving the truck in any temp weather the oil temps rarely see 175. Towing my dune buggy or the small enclosed trailer, never goes over 200°, except on steep grades, in lower gears. Moab BB23 never had a trans oil heat issue, lot of 2nd gear only driving. Only came close to cooling system over condition on the up hill switch backs, so i turned off the a/c, no more problem. I have not pulled the boat with this truck since acquiring my 01 8.1 burb it is now on boat duty.
I no longer trust the temp sensor switches offered by Derale, there are many many reviews complaining they do not last. I have the same experience. I do not know when mine quit but the first time I really need it to work it did not, at only a few months old. My current fan is manual switched, to ignition hot. Both temp, and manual switch were/are ground side relay controlling, no fan loads through either. If I forget the fan the oil does get hot rather quickly, I would like to find a quality temp sensing switch to use, so it can automatic. Sometime My brother or the wife drive the truck, Can't expect them to know all odd quirks on this truck.
One other item that might have skewed my results, My 1st temp gauge failed, and was replace prior to BB23. This is where my trans cooling saga stands.
I hope I haven't confused or muddy up the topic to much.