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Will a 400 transmission fit on 305 Chevy caprice engine?

A TH400 transmission *can* be adapted to a 305 Chevy engine in a Caprice (or any other GM application), but it's not a direct bolt-on. You'll need the correct adapter plate and possibly other modifications depending on the specific year of the engine and transmission.

The challenge lies in the bellhousing pattern. The 305 uses a small-block Chevy bellhousing pattern, and the TH400 was used across many GM vehicles with different bellhousing patterns. You'll need a TH400 with the correct small-block Chevy bellhousing or an adapter plate to mate the two.

In short: Possible, but not without some work. You'll need the right parts and potentially a mechanic's expertise.