So i am running a homebrew campaign and there is this big new crime syndicate called the midnight blades ( because they do their operations at midnight and all their weapons are made of black steel) and my first big bandit cell I’m planning on them taking out is a monster smuggling operation/ gladiator fighting ring. So I have a few ideas on how the players might stop the ring the first being brute force which is just brute force and if they do that I am going to make the encounter ridiculous so they are captured so then they have to fight in the ring against an elder grick or some other monster. If they sneak in I am planning on the people catching them and if they do they are going to be thrown in an oubliette and have to escape. Looking for feedback on whether or not these ideas are good or not and how I can improve them. Not trying to railroad them I’ll make the encounters hard but not impossible.

I guess my advice is to be prepared for the players to think of a third option. Players will often do something random to throw a wrench in even the best-laid plans.

If you're planning on presenting them choices, be sure that they're aware of them all. For example, maybe have two NPCs that are allies of the party arguing. One wants to storm the place (brute force) the other wants to sneak in. There are plenty of other ways, but be sure the party knows they have options, otherwise they might just assume you wanted them to follow a path and then feel railroaded.

Also, it's generally not a good idea to have scripted failure/death. As in, "if they try to take down the ring by force, they'll get captured and have to fight in it." or "if they sneak in, they will be caught and imprisoned." Maybe keep those in mind as failure states if they fail the combat scenario or fail to be sneaky, but it takes away player agency to make sure they fail no matter what. That works in video games, but almost always goes poorly in TTRPGs. It makes it feel like their choice was meaningless and their actions don't matter if no matter what they do, they end up captured.

I'm possibly going to sound rude here but it isn't the DM's job to come up with ideas on how the player characters do anything.

Think of your role as DM to build the escape room/adventure playground/theme park. By all means have an intended solution, but beyond that everything ends up in the hands of the players. Players are creative chaos agents and they'll surprise you often. At the moment from the way you've described things you've got a film or novel, not a TTRPG game setting. Let me explain why. Your quest hook is that they're being paid to 'take out' this smuggling ring right?

Okay, what happens when your players face off against this ring's organisers and negotiate that the ring will simply leave the city?

What happens when the party simply decide to unlock all the monster cages and let 'nature take its course'?

Even better, what happens when the party decide to collect evidence and then hand it over to the city guard who then arrest the entire smuggling ring in the middle of a big deal?

See what I mean? You've possibly intended the party to kill everyone involved in the smuggling ring. Like a djinn, players will often take other interpretations of tasks. As a DM, part of your role is to go with what they've decided to do. This is especially important because it's getting more frequent that I see DMs moan that the players simply aren't interested in their carefully crafted adventure and custom world. Sometimes this happens. You spend loads of time building out a quest and the player response is 'no thanks, we're going to go and track down this random NPC we heard about in passing.' Don't misunderstand you absolutely get to put the playing pieces out on the board, but once they're out your influence over those pieces becomes the lowest order of preference.

How can we fix this then? 

Well, you've got a fighting ring of sorts where people can be thrown into combat with a monster. Maybe the most stealthy way of getting to the back office is through the rafters of the building above the gladiatorial pit? In which case, you've set up the field so that there are two ways the party could end up in there: the party get seen or heard while trying to sneak through the building and are told they'll get to live if they beat the monster in the pit; or the party fail on an DEX skill check to get across a particularly narrow rafter, fall and boom, they're in the pit. You haven't put fingers on the scale and guaranteed they'll end up there, but you've increased the chances of it. 

While we're discussing stealth a DM doesn't simply say 'aha, you tried to sneak in but you got caught'. That isn't the way this game happens. You either choose what type of enemy from the Monster Manual is 'on guard' or potentially keeping an eye out. That monster will have a passive perception. The party roll their stealth against this. If the party all roll higher, they don't get seen or heard. Hard locked outcomes like 'try to sneak in and you'll 100% get caught' remove chance and player agency. Generally that's considered bad form. You can certainly have it in mind that if the party fail their stealth checks for sneaking in the smuggling ring will throw them in a prison somewhere, it just shouldn't be a foregone conclusion. What if they get caught and one of the players asks to run a Deception, Persuasion, or Performance check to talk or act their way out of the situation?

In short, it's fine to have intentions just don't have certainty. The game really doesn't work that way.

Thank you dizzy I don’t want my players to feel railroaded

I didn’t intend to make the checks impossible just hard 

Quote from Furrybeardedmonk_198654 >>

I didn’t intend to make the checks impossible just hard 

My apologies if you feel misquoted or misunderstood. We did only have your initial post and the words you chose to use to go off. Unless there's compelling reason, I tend to take someone's post at their word. In this case the wording 'If they sneak in I am planning on the people catching them' read to me as if this was an inevitability. If players do X, the consequence will be Y.

It’s ok rereading it it did sound like railroading 

Have you prepped the dungeon/encounter yet, or are you still theorycrafting?

It might help to find a battlemap that you really like and pull inspiration from there. Most maps that I've found don't really take stealth into account, unfortunately. So if you're allowing your party to try to sneak in you might have to get creative. For example, saying that there are rafters above where the party can try to sneak and offering ladders down at certain locations. You can use ladder stickers in the Maps VTT for this if you don't have any map making tools.

The map is the main thing players will try to interact with, in my experience. Especially in a combat or stealth sort of situation where there are few opportunities to roleplay or talk to NPCs. I find it's much easier to heavily modify (or even rewrite) the encounter I had originally planned to fit a pre-built map than build my own map or try to find a map that perfectly fits my encounter. So step one might be to find a cool-looking map if you haven't done that already. Step two can be designing the encounter and figuring out how NPCs and enemies interact with the environment. For example, if there's a patrol avoiding a specific square that might be an indication to your players that it's trapped. Or if an NPC climbs up a patch of vines, that signals to your players that they can probably do the same. Try not to add a bunch of little things specifically for your players to find or interact with, because there's no telling what they'll do until you start playing.

That's all assuming you're using a battlemap for the encounter. If you're playing theater of the mind or drawing boxes on a wet erase mat or something, then you can disregard everything I said, lol. This advice is generally applicable when building most encounters in the VTT, at any rate. It's far from the only way to build out an encounter, but it feels the most natural and least time consuming to me.

I am still crafting the encounter considering this is a couple of sessions away

Thank you all! This was very helpful.