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Q: delayed transmission up shift on 1997 Jeep Grand Cherokee

I have a 1997 Grand Cherokee with 188,000 miles. On cold days- under 50 degrees, the first time the vehicle is driven out of the garage, the shift from second to third gear is delayed. It stays in second for an extra 3 -5 seconds than normal (automatic transmission). After it shifts from second to third the first time, there is no more delay. This event is recurring.

Is this problem due to a shift solenoid problem or a clogged transmission line or filter? Or something else?
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kind of late but did you ever find the problem? i have the same problem changed fluid and filter. it will stay longer thatn 3-5 seconds sometimes i have to step off the gas for 3-5 then it will kick in
Not long after I wrote the first post, the delays started extending longer than the first shift and other gears. I took the vehicle to a mechanic for a transmission oil and filter change. But the mechanic advised me that the service would most likely not eliminate the issue and advised me not to waste the money. He said the tranny was wearing and to just baby it until it failed and then bring it back for a rebuild instead of wasting money on the fluid and filter service as it would not fix anything. Not long later due to other issues with the SUV I traded it in for a new car.
Check the fluid level first, then check for any trouble codes in the transmission control module. If those are OK you can try replacing the fluid and filter, but I suggest a diagnosis first to avoid waisting money on un-needed repairs
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