I have a 2006 Liberty Sport, just hit 90k miles. Bought it as the second owner at 65k about 5 years ago.

Around last Spring, I started having trouble starting it. The only thing that I've really ruled out is that it's not a battery issue.

The first, and most catastrophic time it happened, I was heading up to a cabin in the woods. I had been driving about 90 minutes before stopping at a liquor store, and then driving over to a grocery store a few minutes away. Came out of the grocery store ten minutes later, and it wouldn't start. It was cranking, but seemed like it was struggling to do so, getting progressively slower over the few seconds I had the ignition turned. Gave it another try, same result, more depressing of a noise. Sat there for another ten minutes or so, hoping and praying that I wasn't going to have to figure out what to do if I needed to get towed in the middle of nowhere, 90 minutes from home, and 20 minutes from my cabin on a Friday night. Gave it another shot, and after some reluctance, it started up. You can believe I was a bit skeptical of it the rest of the weekend, but I didn't have any more problems.

I've had similar experiences a handful of times, enough that I'm concerned, but not consistently enough that I want to take it in unless I have a decent idea of what the problem may be. I haven't been able to intentionally recreate it, but I have noticed some trends in when it happens:

If it happens, it's usually after I've been driving for about 60-90 minutes. Shut it down, and try to start it up 10-20 minutes later, and that's when you tend to get the issue. Thus far, it doesn't seem to happen if you try to restart the jeep immediately after turning it off, nor does it seem to happen on a cold start, but those are just my observations.

I'd really like to not have to doubt my Jeep like this, but I also don't have a garage right now that I trust enough to send on a "it won't start, sometimes, under very certain conditions" goosechase, so I'd like to get some ideas of what I might be looking at. Any thoughts, fellow jeepers?

If it is a CRD; your signature does not say. Two thoughts come to mind, does it throw any codes (DTC) when this happens, and second, have you ever tried pumping up the fuel head when this happens?
Reading the codes with a good code reader may narrow down what the problem is if it stores any DTC's?
Does it have the second generation fuel filter head?
If by pumping up the fuel filter head manual pump till it is good and hard and then it starts, then you have a air in fuel issue which is most common on CRD's. Adding a lift pump or an in tank pump like a lot of us have done will cure that problem...
Gotta start with the basics....

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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

If it's a CRD the problem sounds like a crank position sensor that's malfunctioning when hot and working once it cools down; a relatively simple DIY fix. If it's a gasser look for a similar sensor.

Also if it's a CRD you need a timing belt job ASAP just based on age and in no case later than when you hit 100,000 miles.

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Sold to LOST member my 05 Ltd, GDE Stg II turbo + TCM tune, SunCoast TC w. Transgo kit, Steiger window regulators, Samcos, Fumoto valve, 2nd gen filter head with Lub. Spec. bleeder, Hayden clutch & 11 blade fan, inverted spare, P-1 battery, BF Goodrich Long Trail TAs, Etecno1 glow plugs, timing belt at 50K miles/8 yrs

No CRD, it's a gasser. I haven't had the "Check Engine" light come on at all, so I hadn't thought to check to see if it throws any codes, but that would definitely be worth a try.

I have used fuel injector cleaner in the past, but with the most recent bottle realized that I wasn't fully following the directions for the most effective usage of it, so I'm kinda hoping that might make some sort of difference.

The gasser also has a crank position sensor (PN 56044180AB) but I'm not sure where it's located. Best I can say from CRD land is if the CPS is failing you will get an intermittent no start or just no start when the engine is hot and a start after things cool down and occasionally a shutdown when running if things get hot. All with no codes or CEL. The check is to pull the sensor; attach an OHM meter; check OHMs while heating the sensor with like a hair dryer; if they go all over the map the sensor is bad. See discussion at viewtopic.php?f=5&t=66905

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Sold to LOST member my 05 Ltd, GDE Stg II turbo + TCM tune, SunCoast TC w. Transgo kit, Steiger window regulators, Samcos, Fumoto valve, 2nd gen filter head with Lub. Spec. bleeder, Hayden clutch & 11 blade fan, inverted spare, P-1 battery, BF Goodrich Long Trail TAs, Etecno1 glow plugs, timing belt at 50K miles/8 yrs