Just started leasing a blue Trailhawk last weekend. Really enjoy over my 13 yo Liberty. Looking forward to the winter package esp. heated steering wheel and seats (and 4WD). Anyway, saw there was an update for the 5.0 Uconnect. Downloaded the 300+GB file directly using Chrome on Linux Mint desktop. Only took a minute or so over FIOS. Tried NTFS formatted 8GB stick. No go - device not recognized. After a couple of attempts tried FAT32 on new 16GB stick and that worked so the instructions are wrong about NTFS. It does take a half minute or so for radio to read the stick and show the update screen. Maybe older sticks are slower and take a little longer. Once it finished and the doors were opened closed a couple times and on/off once or twice, all seemed OK except presets vanished. Put the stick back in to see if it really updated and when the update screen came up, the old and new (on stick) numbers matched so the update definitely took.
Things I've noticed with this latest uconnect: it does seem to find my Android 5.1.1 phone automatically pretty fast now. Older version forced me to connect manually (ie click a couple things on the screen). I tried a voice-activated call HOME, it then found two 'H' items in my contacts. First one was HOME. It asks for the number of the item in the list to call, I said 'ONE', it then proceeded to dial the first number at the top of all my contacts (an 'A..' contact), not the first one of the two 'H..' contacts it identified. Not a useful feature with this bug in it. Bluetooth audio stream seems to experience minor dropouts but not continuously, just randomly. Happens with anything I play so isn't source and never happened in my other car with same phone so I think its the radio or more likely the uconnect software.