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Well, that's a bummer.
Thanks for the answer!
It's not a bug. You didn't find the right place to deliver. Wrong address.
Go to Waukeen's rest if by force is auto trigger/fail delivery, no biggie because Zhent Outpost Leader will just lit and sacrifice everyone on the ground and ran further into the caves; go by sneaky you can choose to wait the Zhent NPCs back there catch up with you and it can go hostile or peaceful either way; Sneaky is get yourself ticket to go into Zhent Outpost to talk to traders and artist below, then can go up to talk to the Zhent Outpost Leader and she ask you to find Caravan Strongbox should Zhent NPCs that perished; since you have it you can hand it over should you didn't tempted to open it - you hand it over after open it she automatically turn hostile and say you shouldn't open it and make everyone in cave outpost hostile.
The problem isn't handing it in there, it's if you negotiate selling it on her behalf. This will in turn cause a half-assed end of the questline with no good place to deliver the chest to .
Unfortunately it seems it is, most are aware you could pawn the box to the zhent hideout, but theres another option you are supposed to have that glitches out, which is what you were replying to
September wants his thread back.
I wonder if you can give it to someone else later on (I doubt it) or regardless of the missing reward, the simple fact of giving it to her could unlock some dialogues as in "oh you are the one that brought the cargo to us", but who knows.
Sad to see it STILL bugged, as I figure it would be a very easy fix.