Hello, I have  a situation where i have a profile drawn on a cylinder and i need to cut a profile into the cylinder with the 3d sketch- but i am failing every time I try

I need to "twist" along the path, as in the cutter that i am using will be always pointed toward the center of the cylinder at the cylinder rotated

I need it to be a .375 diameter cutter, and when i try to sweep a profile or solid it gives me rebuild errors.

any suggestions would be appreciated

As a side note is there a way to fillet the "profile to cut" 3d sketch??