So today i did some work on my 69 Cutlass, nothing close to the tranny but I was removing the bolts in the wheel well to take off the side fenders and once those were out I noticed I had a nice little puddle of tranny fluid on the ground. I didn't mess with anything under the car that would rupture the seal or anything. Not sure what could have started the leak.

 

Normally I lay under there and look up.

 

If it has been parked any length of time, and then they begin to be driven,
all kinds of things pop up. I'm thinking the front seal on the trans or possibly a
cracked or loose cooling line.

 

Sounds like the trans tail shaft to yoke seal is bad. Look at where the drive shaft inserts into the trans. This leak will be more noticeable with the front end up in the air or parked on an incline, front end nose high.
If it is the problem, while your gently removing the seal inspect the yoke for any grooves. Replace it if it has anything deeper than you can catch you finger nail on. Replace it with a HD truck seal for a TH350. Pack the back side of the new seal with Vaseline to help keep the spring in place. Lubricate the yoke with trans fluid before inserting it. MAW look at both UJoints too. Replace with Spicers if needed.

 

Alright thanks, I'll look into the seals and stuff. It had been sitting for a little bit before I got it so that's probably the problem.