There was an update for the UConnect software for our 2016 Cherokee Trailhawk, so I downloaded the update to a thumb drive as instructed on the UCconnect site.
What exactly was updated I’m not too sure – it’s too bad they don’t include release notes, so that owners can verify that features behave as expected, and also to learn what new functionality the system has.
Anyway, I also discovered that the instructions on the UConnect site weren’t very accurate.
Tip #1.  Download the update to your desktop, then extract the enclosed files to the thumb drive.  Not within a folder, and there were 2 files for this latest updated.
Tip #2.  The instructions on the UConnect site state to put the vehicle into Run mode, but without the engine running.  This is done be keeping your foot off the brake pedal, and pressing the start button twice.  Problem with this is that the update takes quite a while – and the vehicle shuts off – which messes up the install.  I ended up calling the 1-800 number provided in the UConnect installation guide, and was advised by a support manager to actually start the vehicle, and then proceed with the update.  Sucks to have to idle the vehicle for the 20 or 30 minutes it takes to do the update, but at least it works!
Tip #3.  Lastly, there was a spot where the screen goes blank for quite a while – 5 minutes or so.  I thought something failed, since the vehicle had shut off as well.  When putting the vehicle back to RUN, the screen remained blank, and unresponsive for just over 5 minutes – which prompted me to call support.  A couple minutes into the call, the screen came back to life, and the installation started over.
Kudo’s to UConnect Support, I was surprised to get through right away on a Saturday – no holding – just had to press a couple buttons after the automated answer and listening to the voice menu.