Simple solution for the dipstick popping out is to bend a small lazy Z in the dipstick to shorten it a bit. Then make sure the ATF level is showing a little over the full HOT mark idling in Park.
Then no extension needed or a need to cut some of the dipstick end off.

_________________
Supporting Vendor and Moderator of LOST
05 Jeep Liberty CRD Limited
Ironman Springs/Bilstein/Shocks
Yeti StgIV Hot Tune
Week's BatteryTray
No FCV/EGR
Samcos/ProVent
SunCoast/Transgo
Carter Intank-pmp
2mic.Sec.Fuel Filter
Flowmaster/NO CAT
V6Airbox/noVH
GM11 Bld.fan/HDClutch
IronrockArms/wwdieselMount
98 Dodge Cummins 24 Valve

I had to post here because I ran into a funny...."solution" to this problem. I am rebuilding a 2006 with broken rockers, and I was having a hell of a time trying to get some component unhooked.

Someone had crimped and bent the transmission dipstick tube back behind the engine. I guess that is one way to solve the problem.

I'll be installing a new tube and dipstick, I'm curious to see if I run into the same issue and will post up if I do.

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2006 KJ CRD 4x4 Sport
ARP Studs, head gasket, HD water pump, GM 11 blade fan/2786 clutch, HD timing set, new rockers
OME Lift, 235/75/16
In tank lift Pump
Yeti tuned!

New dipstick tube is in, good lord I never want to install another one. It was more difficult than the timing belt. My dipstick does pop out as well, if I don't have the stick oriented properly, otherwise it hasn't been an issue. I'm just glad the tube was still available. it was bent 90* over behind the cylinder head, who does that!?

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2006 KJ CRD 4x4 Sport
ARP Studs, head gasket, HD water pump, GM 11 blade fan/2786 clutch, HD timing set, new rockers
OME Lift, 235/75/16
In tank lift Pump
Yeti tuned!

The seems to be no consistency with the dipsticks working their way out. When I first bought my 2006, it did it all the time. After I replaced the trans fluid and used a real gasket on the pan, it never popped out again for 60000 kms. Then, after completing the second timing belt change at approx. 300000 kms. the trans dipstick started popping out again. (the trans pan was not disturbed). Now I just use a tie wrap to hold it down.

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2006 KJ Sport CRD, 2006 KJ LTD CRD, 2013 Subaru BRZ 6spd., 1994 Ford F150 XLT, 1969 Dodge Charger R/T 4spd. (Yes it's a Hemi).

The reason the dip stick pops out is the tip of the dipstick comes in contact with bottom of the OEM oil pan preventing the dipstick from staying fully seated into the tube. See Picture 1
The fix for a vehicle with a stock pan is to either cut a small length off the end of the stick and then remark the level markings
or
Bend a lazy "Z" in the dipstick to make it shorter so it does not contact the oil pan. See Picture 2
or
Install a deep sump oil pan, problem is solved. See Picture 3


Picture 1


Picture 2


Picture 3

_________________
Supporting Vendor and Moderator of LOST
05 Jeep Liberty CRD Limited
Ironman Springs/Bilstein/Shocks
Yeti StgIV Hot Tune
Week's BatteryTray
No FCV/EGR
Samcos/ProVent
SunCoast/Transgo
Carter Intank-pmp
2mic.Sec.Fuel Filter
Flowmaster/NO CAT
V6Airbox/noVH
GM11 Bld.fan/HDClutch
IronrockArms/wwdieselMount
98 Dodge Cummins 24 Valve