Retractable work light doesn't retract

Some times my HF retractible extension cord does the same thing. I have found that pulling it all the way out and carefully letting it retract forcing it to wind side to side gives some extra room inside and the rest will fit in too.
Yep, 2 possibilities. This above where cord is stacking wrong and won't fit can usually be resolved by how it feeds in. Or is it out of spring tension at that point? If that, it is either weak, or lost position. Then it depends if you can get it to wind up tighter. I would guess that is gonna vary between makes whether it can be saved...I'd certainly open it and check before giving up on it. I opened one up and it had rotary contacts that were about shot anyway so scrapped it.