Recasting Question

Suppose you had cast Fragility on an enemy, if you in someway cause them a condition, but that condition outlasts the duration of Fagility, can you cause that condition to them again, while it is still on them, and set off Fragility again?

If they are already affected by the condition, all that re-inflicting the condition will do is reset the duration on the condition- it won't trigger fragility unless they aren't already affected by the condition. An example- using Sever Artery- you can use this every 5 attacks or so, but if they're already bleeding when you use it, they won't take damage from fragility- though the duration of bleeding from your Sever Artery will be reset.