Troubleshooting a Home Wiring Issue

My home has been previously wired for a security system (although to my knowledge has never actually used one), and the labels on the wiring was mostly illegible, so I began the process of identifying which wire goes where.

Everything was going great until I couldn't identify the wire that went to a single window. Using a tone tracer and a process of elimination I believe I was able to identify the wire, but there was no continuity with the window open or closed. Believing it might be a problem with the contact sensor itself I took it off to access the wires themselves and still no continuity.

Stranger still, attaching the tone generator to the WINDOW end produced no tone at the other end  in the basement, whereas I do vice versa.

Does anyone have any idea what could be going on here? Thanks in advance!

Ended up being a fault in the wire at roughly the place where the toner died behind drywall. No easy solution, had to take out a patch of drywall to repair wire where it had been damaged.