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Will a 350 engine from Oldsmobile fit in 1990 305 caprice and if so what type of modification will you have to do?

Yes, an Oldsmobile 350 engine should fit in a 1990 305 Caprice with some modifications:

- Exhaust: Ensure that the Oldsmobile 350 engine exhaust manifolds line up with the existing exhaust system. If not, custom manifolds or modifications to the exhaust system may be necessary to match the placement of the exhaust ports and connect to the exhaust pipes.

- Fuel: While the fuel injection system from the original engine may be usable, depending on compatibility, it's recommended to ensure the fuel delivery aligns with the requirements of the Oldsmobile 350 engine. This might involve replacing fuel injectors, fuel lines, and potentially installing a new fuel pump and fuel pressure regulator to handle the increased fuel flow needed for the larger engine.

- Electrical: The wiring and electrical connections need to be adapted to the Oldsmobile 350 engine. This includes linking up the engine control unit (ECU) and sensors such as the coolant temperature sender, throttle position sensor, and oxygen sensor. Custom wiring or reprogramming may be required to make these connections.

- Mounts: The engine mounts from the original engine should be compatible with the Oldsmobile 350 engine. However, some modifications to the mounting points or custom engine mounts may be needed to ensure proper fitment and alignment of the engine.

- Transmission: The original transmission from the 1990 Caprice may not be compatible with the Oldsmobile 350 engine. If necessary, modifications or a compatible transmission would be needed to work with the Oldsmobile engine and handle its torque and power output.

- Cooling System: Modifications may be required to integrate the Oldsmobile 350 engine's cooling system into the Caprice's. This might involve modifying or replacing radiator hoses, adapting to the water pump, and ensuring adequate cooling for the larger engine.

- Driveshaft: Depending on the changes in drivetrain length due to the engine swap, the driveshaft may need to be shortened or replaced to fit the new driveline dimensions.

It is highly recommended to consult with experienced automotive professionals or mechanics who have expertise in engine swaps and modifications to ensure the process is done safely and correctly.