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so im looking at a few subaru outbacks from the early 2000s and late 90s. how can i tell if the head gasket is on its way out? just so i can stay away from that particular vehicle.
 

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2002 Subaru Outback H6 L.L.Bean
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Look for milky oil in the engine oil, and for oil in the coolant, and smoke when you start the car. If the fluid levels are strange, like high oil and low coolant, that is a good sign. Look for external leaks where the head gaskets are located, although rare, it is not impossible.
 

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OBW H6 VDC, Tribeca, XT6
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Look for milky oil in the engine oil, and for oil in the coolant, and smoke when you start the car. If the fluid levels are strange, like high oil and low coolant, that is a good sign. Look for external leaks where the head gaskets are located, although rare, it is not impossible.
those kind of generic old school headgasket failure modes and are not helpful for Subaru's.

so im looking at a few subaru outbacks from the early 2000s and late 90s. how can i tell if the head gasket is on its way out?
You are asking about headgasket issues - which are EJ25's. They have very specific headgasket failure modes depending on which EJ25 you're talking about.

Coolant does not get into the oil and oil does not get into the coolant. If they are bad enough for that to happen the engine is toast and you won't need help figuring that out. Compression tests are also pointless on these motors, don't waste your time or money on them. And don't trust a mechanic who thinks it means anything for this motor, it doesn't.

Phase I DOHC EJ25's (all 96-98 EJ25's and 99 OBW/Legacy) fail by pushing coolant into the exhaust. The only way to test those is to have the coolant tested with a "block tester". Or drive it and hope it overheats while you're driving. That is the only consistent test for the initial headgasket warning signs for that motor.

Phase II SOHC EJ25's (99 Forester and 99 Impreza RS and all 00+ EJ25's) leak externally. With two distinctions:
2004 and earlier they leak coolant externally and sometimes oil externally. Visual inspection is all that's needed.
2005+ usually leak oil more often than coolant but same thing, visual inspection is all that's needed. You usually have to discern wether it's the headgasket or valve cover/oil cooler gasket though since they can be easiliy confused.

So the good news is - all you need to do is inspect it well visually and it's either leaking or it's not as they always leak externally and very rarely internally - and those are probably ones that have already been previously worked on/repaired/overheated, etc.

Unless it's an EJ22 or you have a VERY compelling reason to buy it I would avoid a Phase I DOHC EJ25, they are problematic and even when repaired properly have such ingrained issues due to the way the piston extends far out of the block (Subaru no longer does this) they simply aren't as robust as the newer versions. Since that's on the "low" end of your list ayway - as you say "late 90's to 2000's"....it seems obvious you should simply avoid them.

One owner vehicles with service records shine here. Off the car lot they don't know jack about the car...they picked it up at auction and flip it. Someone selling a car out of their house is not likely selling something with a blown headgasket...those end up in the auction yards and used car places.
 

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Meh.
I has wagons.
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grossgary nailed it.

1999 and older: classic internal leak signs. Bubbles in coolant overflow bottle, overheating, etc.

2000 and newer: rarely overheats unless run low on oil and/or coolant. Look for leaks or sign of a recent cleaning that may be an attempt to hide them.

FWIW, I find the SOHC Phase II engine much friendlier on my hands to work on, fewer busted knuckles.
 
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