Telecaster582
Tele-Holic
It does when I put it in the cleaning paste. It has a nice shiny tipIt looks to me like you are cleaning a ruined tip. How do you clean it? Do you tin it after cleaning? The tip in that picture has a coppery color. It should always be bright silver from tinning. Once they become corroded, they just don't tin properly. If you have ever cleaned the tip with sandpaper, it is also likely toast. And tips DO wear out. Cheaper tips wear out sooner because of cheaper alloys used.
Start over with one of those unused tips, tin it before you start, and tin it immediately after cleaning it. Try to buy brand name soldering stuff - it isn't that much more expensive and have more dependable tips and temperatures.