The group is lost in the underdark. Everyone they've encountered is hostile and tries to either kill or enslave them. One of the PCs has the criminal background that has the feature that they can get a message to their criminal contact. I'm not going to invent a (relatively) friendly smuggler just so they can pass a message along. Perhaps once they figure out how to survive and somehow establish at least a temporary truce and relationship with the locals it can happen. But when every time they encounter other humanoids it's quickly followed by "Roll for initiative"? No.
I wanted to take a moment to address this because I think it's very illustrative of different expectations about agency.
If I'm running part of the game in the Underdark, I have to decide what my goal is here. The Underdark is one of those amazing parts of the D&D world that's dangerous, scary, and filled with wonder. What do I want to do there? Am I going to run a bunch of encounters where I describe what's happening and then move to "roll for initiative!" Yeah, some of them are going to be like that. Unintelligent monsters, horrors live there and it's very dangerous. I want to establish that. I hear there's a fat red dragon down there.
And at the same time, there are intelligent factions, drow, duergar, mind flayers ... you name it. All of them are vying for power and control. And here we have a group of powerful outsiders (we know they're powerful because they aren't
dead from the horrible monsters yet). This is an opportunity to have some outsiders do my dirty work for me and get rid of an enemy faction while keeping my hands clean. And at this point, I'm thinking of the movie Yojimbo here.
The fact that one of the characters is a criminal who has contacts everywhere gives me the perfect opportunity as the GM to introduce a high-stakes diplomacy element to the game. Sure the dark elves have heard of that criminal faction! What a perfect opportunity for them. Sure we'll help with supplies and information, but
you need to do something for us in return.
What this does is link the characters to the larger world. It makes them feel like they are a part of something bigger.
That was one suggestion that I thought of about how to handle a criminal background in the Underdark. There are many others. Maybe the creatures want to use that surface level criminal syndicate to have connections on the surface for nefarious purposes. Or countless others.
Those are ideas as to why the character's ability might make sense to use in terms of the game, and they would turn things into more negotiation, diplomacy, and hard choices (do we really want to help out a group of drow slavers?) It gives the players a feeling that their choice to be a criminal
mattered, and that's agency in a nutshell to me. That's a different game than "you enter a cavern, there are a party of duergar there, roll for initiative!" Which is better? I'm not willing to say objectively better (and my 2023 motto is "don't yuck in someone's yum") but I know which one I'd prefer.