D&D 5E Advice Sought: Running an NPC prisoner interrogation

We ran it. The group tried going tough guy first and there was little give. When the nice guy went at the dwarf things were going well for a bit, but eventually he clammed back up due to some failed roles and reminder of why he tried to kill some members of the group in the past.

The group then used a custom magic item, a crown of forgetfulness, to take the conflict out of his memory. Then they used deception to convince his absent minded state that they rescued him. Through that fake friendliness they nabbed a few more details.

Eventually someone used minor illusion to create the sound of his mount nearby (a wyvern). He wanted to leave and they let him go, still wearing the crown. Since all were surrounded in fog they again cast minor illusion off in the distance and he headed that way.

A little mage hand took the crown of forgetfulness off, another screech of the wyvern and he disappeared giving them 80% of the possible intel with very little torture and every PC doing something.

Was it fun? Live up to your expectations? Players?
 

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Yeah, it was definitely enjoyable for me and the players. I like that they mostly succeeded, but not completely.

Very cool. Let that be your benchmark, and watch to make sure it doesn't get out of hand for your group's fun.

A lot of us are trepidatious because we've screwed up before. (A lot of us had nobody to ask for help).

But I'm glad it worked! It opens up future stuff for you.
 

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