D&D 5E Need help subtly letting the player know they've dropped the ball

[Satyrn]

If you want to mess with the pc's(who doesn't aimiright,amiright?) I would place another npc there who knows all about Leosin but wants to be rescued himself!

I am totally reminded of the Life of Brian. After he's rescued you should have this imposter NPC whistle a lot.

 

[Eis]

prisoners with NAMETAGS

think about it

think about it

 

[Dit464]

You could have them go through a ledger or other written notes that could pertain to the prisoners, they could either slice through the captors, bargain/scheme for the information, search for the list and look through it before they get caught -or steal it, I assume they might forget what it says otherwise- Most prisoner lists back then would just be the name of a prisoner with a short description of the prisoner; their facial features, tattoos, body style, race, etc. Although I am genuinely surprised that they just up and left not caring about knowing who they were looking for, however, as a DM you can go pretty much anywhere with this situation. Force them to purchase his freedom, accidentally kill him and have to find a replacement or revive him, force them to break ties with the captors when the captors start getting rid of their prisoners -sold, moved, executed-
If you feel like being a little mean have them jump more hurdles by putting them in situations that are much harder/time consuming.

 

[kalil]

They have created a problem. Good! Now let them figure out how to solve it. Dont tip them off. Dont force information down their throats. That is just rail roading.

 

[S'mon]

Personally, I always take joy in watching the party flounder through their own fault.

Me too - nearly as much as I take joy in watching them succeed through their own efforts.
You can't really have one without the other. In this case, as usual, I would just let it play out naturally, with them potentially not finding the guy & not knowing.

 

[S'mon]

I was thinking this but i think they'd enjoy just dealing with the problem they've given themselves...

Yeah, you definitely want to just let things play out naturalistically with these guys.

 

[GHammy26]

I've figured it out thanks to you guys.

I've got two areas in the prisoner camp where the captives are being kept. In one there will be Leosin although he wont respond to his name incase the captors are looking for him specifically (really dislike the idea of explaining that he wants to be there and the dragon cult know that he wants to be there but want to know what he knows so have captured him etc, its just lame in my opinion...), in another tent is an imposter who will respond to the name Leosin as he is a spy/assassin placed with the prisoners to try and find him.

I won't just tell the PC's what Leosin looks like, I'll have it as information they can exchange from the prisoners for their freedom. I have quite a few Prisoners for them to release so if you guys can think of some really quirky/strange descriptions some idiot prisoners can give them e.g. "He has some of those legs... you know that you don't see on everybody..." it's no help but the players will enjoy the frustration.

Anyway to cut things short. they can try and find Leosin out of the prisoners when everyone is out or they can just go off with the imposter who will try to assassinate the Lord. My players are lazy and uncaring sometimes so this may make them rethink their 'smash and grab' tactics.

Thanks for your help guys!

G