Yay - pulled that big cable out of the wall, after fighting with it yesterday.

Three things seemed to help. A syringe of liquid soap for the hole, scraping caulking away from the wire with a paint scraper and a forstner drill bit for the tight spots, and then pulling it a bit further the wrong way first to further clean the cable, and soap it a bit.

Whew. Another ten minute job completed with only three and a half hours of effort.