Cat, I hope you don't mind I anticipated your actions.
Cat grabs the crowbar...For SheShe's sake this better work this time.and approaches the dragon in a non threatening way. With Ashley working on her lead and since Cragmaw will eventually be able to break her leg chains, she naturally attempts to break her wing chains.
Good luck! RNG gods be damned! [1d20+4+1d4Guidance=(19,23) vs DC20]Cat manages to break the chain, freeing Cragmaw's wings.
Cragmaw lets out what could only be considered a laugh and seems to smile widely as her wings strech out. She winces as they reach full span, sore as they are for being bound. She then bites at her leg chain.
[1d20+4=21 vs AC19]Her teeth bite in, spreading the rings[1d10+2=11]and she manages to break them. As they fall to the ground she hops and bows her head while Ashley pulls on her lead causing it to slip off. With a loud roar she beats her wings and after a few painful attempts she manages to take off. Soon she's soaring off above the clouds. Dragons don't forget those who help them, nor those who wronged them, perhaps some day you may meet again.