Re: What are some of the issues you have see with the 8 speed Transmission...
At 39,000 or so miles the transmission began to misbehave and soon failed. Under warranty, the transmission valve body was repaired or replaced. At 41,000 miles the transmission failed again. Jeep then replaced the transmission with a remanufactured transmission under warranty. No problems since then, but I always fear another breakdown. I will certainly sell or trade in the Jeep before the 60,000 mile warranty ends.
2014 Jeep Grand Cherokee Overland 3.6L 4x4; Quadra-Lift II; ORA II; Advanced Technology Group. Built April 2013. At 41,000 miles transmission valve body assembly replaced under warranty. At 43,000 miles (70 000 km) transmission replaced under warranty. Now has 58,000 miles (87 000 km). Goodyear Wrangler All-Terrain Adventure with Kevlar tires.