For some reason I'm unable to give a key to spidey specifically. He says he used an old key (2017) for his Goliath and is thinking he may have messed something up. This was also while he and I were in the same sector, both with our Goliaths in sector, both undocked, if that matters.

Are you able to give keys to anyone else?
If it continues to happen, try disabling all of your plugins and try again.