When the engine is off the fuel common rail loses the fuel pressure .
When the engine is being cranked the fuel common rail fuel pressure has to reach about 3600 PSI before the engine will start .
If air is leaking into the fuel system and there is air in the common rail the common rail can not easily attain 3600 PSI under cranking because the air is being compressed .
Some good information at -
www.oregonfuelinjection.com . Article - Jeep diesel diagnostics , 2007-2008 3.0 l Jeep Grand Cherokee .
You need to crank the engine with a scanner hooked up and read the fuel common rail fuel pressure under cranking to see what is going on .