1996 Grand Cherokee oil dipstick won't go in tube.

That means that the rings are bad and that the motor needs to have a full rebuild put into it or get a new motor. Exhaust is going past the rings into the oil chamber and comming out the dipstick tube.

The PCV system is supposed to pull vac on the crankcase to re-burn the fumes in the oil pan.
But your engine sounds like it has a vent problem via the air filter.

Push it in till it sticks, remove half way (so 1/4) of travel turn dipstick 180 degrees then push in if jambs again try 1/4 way out & turn 90 degrees. Sounds stupid but this normally works with vehicles haveing trouble getting dip stick in. Just don't force to much.

Sounds like you have one or more faulty compression rings. This is not a DIY job and will be costly. What does the oil pressure gauge read?

Oil Heater,,,the auto parts stores have an heater tube you insert into the dipstick tube,,,its a cheap fix,,usually about 20 dollars,,,keeps oil warm and provides quick starts,,,other fix's are expensieve,,so this is the lowest cost method. good luck. Tim.

the transmision dipstick will be coming up from behind the engine by the firewall, a lot of times they have a red handle on them, sometimes not... really dont know how to explain, other than the dipstick tube will be coming up by the firewall. hope this helps you

code readers cant.the scan tools can but are real expensive.if you havent drained the trans oil yet just drive it around a while and check it.if you have drained the oil then try to measure what you took out and put that much in.if you cant measure old oil then add fluid while engine running in nuetral{double check the nuetral position writen on dip stick} add fluid untill oil is below the add level let it run for a while say 30 minutes and recheck add th full then go drive it around.recheck again if low add if high drain out or siphion some out throuh small hose through the dip stick tube

Not a problem ... it is simply wedged into the crankcase. It has an O-Ring for a seal.
Be sure to coat the new O-Ring with motor oil before inserting the tube.

Also, measure your oil level if you can and check it afterwards. The dipsticks may be different in length (not too likely).

Assuming its automatic, filler is on the right side passenger firewall (fills through dipstick tube) Make sure you check level with vehicle running and warm. Add less than you think you need. Though you can overfill just a bit, going too far will cause fluid to be frothed up by internal components and give you big trouble. If stick, there is a plug on the side of the unit. Check level with your finger. If you can touch it without "sticking your arm inside", it's good. Check with vehicle on level ground (either trans) Stick fluid is added through same hole.

This tube should not be capped off. It should have a yellow or possibly red clamping style dipstick in it. Also this tube should not be rubber, I believe they are usually made of a harder plastic. Based on this I would consult a technician. You should be able to go to a smaller shop, go in and ask them to take a quick peek, they will normally be more willing than a large dealership and won't charge you just to look.