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I just bought a Trailhawk. I understand that the a Trailhawk is a "sometime" four wheel drive controlled by the "Auto" option. How can I tell if "Auto" is choosing two or four wheel drive at any given time? Does any choice besides "Auto" (sport etc) force the Jeep to four wheel drive?
 

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Jeep has a couple of pretty good videos explaining the drive systems. Look on the Cherokee page under the "Capabilities" tab.
 

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2019 Jeep Grand Cherokee Trailhawk Hemi Lux Group
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http://www.jeep.com/en/2014/cherokee/#model=limited&color=deep-cherry-red

Scroll down to Capability. The short version is the Jeep will be in FWD most if not all of the time. If you set it to Sport you will shift power to the rear and shift points are modified.

You can watch the ADI video to understand how the transfer power unit works and then move on to the other two.
 
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