I've never had that happen to me. I've done a fair amount of desoldering, swapping components for testing. Preheating doesn't hurt, but I've never had to do it.
Extra flux helps, depending on the braid.
I always turn the iron up higher. Upwards of 650F-700F. For SMT pads, I apply flux, do a visual and watch the solder flow into the braid and then roll off with little pressure applied to the braid (roll it off with the iron).
Through-hole takes a few tries to empty the hole. Hit it once, once the smoke comes, roll off and look. If it's not clean, apply more solder, then more flux, and repeat with the braid.
It's messier with more flux, but I find it works better. Some braids don't need more flux, like the RatShack braids, surprisingly.