It may work if you take very small steps, or put a blend on the edge between the cylinder and the cone.
A different approach is to use the original pin and get the step to end where the cylindrical face is near the end of the hole by editing the displacement value, then use Contact Step Controls to Deactivate the frictional contact between the pin and sleeve in the next step. At the end of that step, it will be as if the pin was not there.
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