I attempted to use the key in the broken lockbox, but no matter what I did, it just make me pick the lock on Inigo's cell. Is this a bug and is it fixable?
The key hasn't been there from the first version but was added later, so if you have used an earlier version and entered the jail it maybe some older data baked into your savegame, just pick the lock or use the console to open it in that case. If you haven't used an earlier version before the key was added you have a mod conflict in the Riften jail.
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Cell Key does not work? (Spoilers) (2 comments)