Can you identify the liquid? Not heard about an AT failure that sprouted a leak.....sounds more like the generic cooler may not have the required connections for the transmission heat exchanger....

Generally sounds like you crossed that "magic" moment where you have all the known drivetrain issues at the same time.

Transmission/TorqConv, V-pan/waterpump/tank. Chain guides/Vanos. It seems to come around 100k.

Belknap has a nice thread about his 100k service that should give you an idea what is coming.....I am afraid it is a but frustrating but it is a reality that the 4.4's develop a bunch of ailments at this point.

Good luck!

__________________
2003 4.4i black ext./black int./black headliner (kid's runabout)
2014 535d X-drive, M package, silver/black interior

Sold but not forgotten:
2009 E70 35d, black ext./black int./black headliner (sold 2021)
2006 4.8iS Le Mans blue/cream int./black headliner, SOLD in 2012 sadly...

Other hardware:
2015 Cayenne S (wife's new DD and definitely wroooommmmm)
2016 Tundra 1794 edition crew cab, luxo hauler
2005 Tundra crew cab, weekend hauler. Sold after 150k very happy miles.