On basement wall penetrations we used rope oakum packed in by driving in with the butt of a cedar shingle, then lead wool same packing, a quick pass with a torch, then more lead wool hammered in. As far as I know, none of them have ever leaked. We didn't have those fancy tools back in the 60's. We did some cast iron soil pipe installations the same way. I now have a complete set of packing & pouring tools and have never used them. My brother-in-law said that the Ohio plumbing license test included knowledge of the lead & packing methods, however, most people today just use good caulking.