AW4 no overdrive when cold (Intermittent)

My 97 cherokee, AW4, 4.0 does not always want to shift into overdrive when cold. The last time I drove on the interstate(level, 20 miles), it took 4 attempts at stopping along side the road, turning everything off, waiting for 30 seconds, then restarting the engine to get it to go into overdrive. Othertimes it will shift into overdrive properly at 42 mph after only 5 minutes of moderate driving. This only happens about once every two months. Otherwise it shifts great.
Any ideas?
Rick........

Not sure about the '97, but on my '92 the switch on the break paddle was gone. It started intermittently before it completely stopped working (no more overdrive, computer thinks the brakes are applied).

A good check is to see if the cruise works when it doesn't go into overdrive; they're on the same switch. So if 'no overdrive' and 'no cruise' that switch may be a place to look.

Just a thought, good luck!

do you have a check engine light on?? i have a 99 and it is doing the same gosh darn thing. has been for a while. pulled code on OBDII and gave me a p0705 code. looked it up in my tranny fsm and it listed about 20 possible things it could be. but troubleshooting them all required a special tester that runs from 3500 used to 8000 new. i have learned to just turn the key back while driving, wait five seconds and put it back to the run position and it usually fixes it. the engine never actually stops turning cause of the torque converter still engaged and it just kicks back on. i'm sure this is not fantastic for it. also.... do your reverse lights and aux fan still work? both of those stopped working at the same time for me. i cleaned my NSS and even tried a junkyard one and nothing helped. other parts i swapped in were another TCM (transmission control module) and this did nothing to aid in the problem either. hope this helps in ruling some things out for you. let me know if you figure something out. also my cruise works fine

Isn't OD not supposed to engage until the ECM sees that the engine has reached operating temperature-thereby being in closed loop? Maybe not though, I speak for GM not Chrysler..

Cruise is operational, engine temp was at 210, I just had to try more than the usual one time to get it to reset. Yes the CEL was on. It always goes off in a day or two. No saved codes, even while the light is on. It is a 97 & I can check it with the key on-off-on test. Seems to be getting worse.
Rick......

Mine won't go into OD when I start it off, I drop the shifter to third for 50 yards then back up to OD and it goes like a champ.