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Can an Oldsmobile 350 engine fit in a 1986 Cutlass Supreme that has V6 If not whats the biggest will fit?

No, a Oldsmobile 350 (a V8) will not easily fit in a 1986 Cutlass Supreme originally equipped with a V6. The engine bay and associated mounts are not designed for the larger V8. You'd need significant modifications, including potentially:

* New motor mounts: The V6 and V8 have completely different mounting points.

* Modified or custom headers and exhaust: The V8 will be significantly wider and longer.

* Potential transmission issues: You'll need a transmission compatible with the V8, and that might require modifications to the transmission tunnel or driveshaft.

* Wiring harness modifications: The V6 and V8 have different wiring harnesses.

* Cooling system upgrades: The V8 will generate more heat and may require a larger radiator or other cooling system modifications.

While *possible* with a lot of custom fabrication, it's a very involved and expensive project, not a simple swap.

The biggest engine that would fit reasonably *without* major fabrication would likely be a larger V6. Even then, some minor modifications might be needed. You'd have to research specific V6 options and their dimensions to ensure compatibility. Finding a suitable, higher-performance V6 from another GM car of the same era (or slightly later) is the more practical route to increasing engine power in your 1986 Cutlass Supreme.