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My 1990 Mustang starts up and runs fine, but once I turn it off after I've been driving, it will not start back up for several hours (I'm thinking a overheating problem). Then engine cranks, but it refuses to get going. I have 3 separate problems that may be the source:
-battery was ancient (has been replaced but not driven since)
-I don't know the last time the coolant was changed, so not sure if it needs a flush (did not check the temp before turning it off, but could be temp gauge related as well)
-Oil leaking from middle, just behind the front wheels

This has happened 4 times and haven't driven it since to avoid damaging it further. Any ideas?
 

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I would agree with the first guy, there are alot of other parts that make up the ignition system, and alot of them dont work as well when theyre hot so naturally as they start to wear out they will stop working at a certain temperature.

things you should check,

make sure fuel lines are away from any sources of heat, (liquid lock could cut off fuel flow)
test ignition control module

the really fast way to figure out if its fuel or spark would be to let it get hot, pull a spark plug and ground it against the engine block while cranking and if it sparks you know its fuel and if it doesnt its an ignition problem
 

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Sounds a lot to me like there most likely is an ignition problem.
If the engine cranks, but doesn't start, then the battery might not be the issue. What you should do when this happens, is first see if you get spark. Take a spare plug lying around, pull off the #1 cylinder wire, put that plug in it, touch the plug to a bare metal spot on the motor, and crank. If you see no spark, then you could have an overheated ignition module. These old Ford modules are known for problems, and chances are, it might need to be replaced.

If you are getting spark, then you should consider the possibility of there being a fuel problem. Although it's hardly the case in vehicles with electric fuel pumps in the tank, you might be experiencing something like a vapor lock condition where the fuel line comes too close to a component that gets very hot, such as the exhaust manifold, or the catalytic converter.

Either that, or you could have some off-the-wall electrical problem that is sensitive to heat and doesn't allow the car to start till after it cools down.
 

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Sounds like a fuel pressure problem. Some routine maintenance in the fuel systems is in order: fuel filter(s), replace fuel pump relay (these go bad and get finicky), check/replace fuel pressure regulator, and check fuel pressure. Vapor lock is also a possibility. That is where the fuel line gets hot and the gas inside vaporizes causing a big air bubble in the line. You won't get fuel pressure until that air bubble is gone either by cooling or being forced through the system. Find the heat source and re-route the fuel line or insulate it with wrap.
 
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