2001 Jeep Grand Cherokee Hard First Start
You could also have a leaky fuel injector. A can of injector cleaner won't hurt anything and could help. Do you notice any smoke on startup?
If it is not holding pressure and you find no leaks (external or injectors) check with the dealers parts service and see if it has a seperate check valve that can be replaced or if it is part of the pump.
In the interim turn your key to the on position (not start) and listen for the pump to run. Shut it off when the pump finishes and then try to start it.
Good luck and let us know. :)
Suggested Repair
Confirm with a dealer whether the fuel pressure regulator is combined with the fuel filter, and replace the fuel filter if it is original. Consider a leaky injector and try injector cleaner if there is smoke on startup. If pressure will not hold and no external or injector leaks are found, check whether a separate check valve can be replaced or if it is part of the pump. As a temporary step, turn the key to ON until the pump stops, then start.
Conversation Summary
A 2001 Jeep Grand Cherokee will not start on the first attempt but starts on the second and then runs well. The battery, starter, and alternator tested good. Fuel pressure holds about 50 psi while running but falls to zero within about an hour after shutdown. The expert suggests checking the filter and regulator arrangement, considering a leaky injector, checking for a separate pump check valve, and priming the system by cycling the key before cranking.
