Anything more then moving the trailer across town or a camp site would scare me.... Just got back from a dirt bike trip out west and we took my buddys dodge 3500 (single axle) and a 22 foot enclosed trailer and it towed great! We were well below the max tow rating for the truck but even still it became exhausting to drive once you throw in construction, rain, cross winds, the continental divide, ect... And this was a safe set up i cant imagine trying to pull it with my JKU. Trailer was heavy duty tandem axle weighing about 3500, 5 dirt bikes, gear, coolers, gas cans, spare parts ect. We think the trailer weighed 6K ish with a truck that weights 7600ish...