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Can the oil cooler on a 1996 350 vortec leak anti-freeze into engine oil?

No, the oil cooler on a 1996 350 Vortec engine cannot directly leak antifreeze into the engine oil. The oil cooler's function is to cool the engine oil, and it's part of the oil circulation system. Antifreeze flows through a separate, entirely different cooling system.

While a catastrophic failure *could* theoretically cause some mixing (e.g., a massive crack in the cooler simultaneously breaching both oil and coolant passages), this is extremely unlikely. A more common scenario would be a coolant leak into the engine block (head gasket failure, cracked block) which would then contaminate the oil, but this isn't a failure of the oil cooler itself. The oil cooler itself would more likely leak oil externally if it fails.