Summary
Rogues are quite a distinct class in Dungeons & Dragons. Surprisingly, they can work well by themselves when ambushing targets, and they excel in many situations outside of combat, such as disarming traps and entering locations without being invited. Still, an isolated rogue in a fight is a relatively easy target, even if they can be fearsome when fighting beside their team.
Still, how would you, the Dungeon Master, ensure that your Rogue player is properly challenged throughout the adventure, especially considering the high amount of damage they can deal to whoever they’re shooting at or stabbing? Well, there’s always a way, especially for someone who controls the entire world the Rogue walks on.

Keep in mind that our goal here is to help you challenge your player, but going overboard on your campaign with the ideas here might make things too particularly hard for them, making them feel personally targeted or even end up killing their character. We don’t recommend using these tips all the time, nor adding most of them in the same fight.
9Focus On The Rogue
Obvious, Sure, But Worth Mentioning
Simple solutions can be very effective. Rogues are squishy and don’t tend to have a high AC (Armor Class) right away, which means that a few strikes on them can be enough to put them down or at least think defensively.
you may have multiple ranged attacks against them or surround them with your melee troops. Either way, a focus fire can even be too deadly here, so be mindful.

They are good at escaping when surrounded, thanks to Cunning Action, but getting close to the character will still force them to waste bonus actions escaping, especially if they are ranged characters since your proximity will give them a disadvantage in the attack.
8Prevent Them From Escaping
Don’t Let Them Run Too Far
As mentioned, a cornered rogue can escape with some ease. They can disengage and dash on the same turn if necessary or even dash twice on the same turn. That means they can easily use their turn to get extremely far from enemies, giving you a problem to deal with.
Long-range attacks are already a great solution here, turning the fight into an interesting shootout rather than a clash of blades. Still, you can do other things, such as give your creatures a bonus-action dash, Legendary Actions that involve extra movement or teleportation, just better movement in general, or spells that restrain the opponent or make the terrain difficult.

7Make Enemies With High Perception
Among Other Tricks
Rogues are masters at catching people off-guard and attacking enemies while they’re surprised. Your rogue will probably even add expertise in their stealth for that. While that is a clever way for them to approach most fights, there are ways to save your NPCs from such a fate.
A simple solution is to give your enemy a high wisdom score and the perception skill, and maybe some particular bonuses for their passive perception if you want to - you’re able to design exclusive features for NPCs. Magic alarms around the location are also fun, along with multiple characters in the area that may notice the rogue. Still, you can give your creature blindsight or immunity from the surprised condition.

6Add Many Minions
They Can’t Attack That Much In One Turn
As mentioned above, a lot of characters can be a rogue’s nightmare. Sure, having multiple NPCs in the same place can also be an annoying scenario for you since you have a lot of control at the same time, but even if it’s multiple of the same creature, that will work wonders.
Not only do more eyes make it easier to detect a rogue that is currently hidden, but one of the weakest details about the rogue is that they only have one attack per turn (unless multiclass is involved). They’re good at causing a lot of damage at once and may even take one of these minions in a single strike, but they can only kill one enemy at a time and can be overwhelmed by a crowd.

5Fight In Open Areas Or During Daytime
Don’t Let Them Hide
Rogues don’t like to stay in the open. They are squishy, as mentioned, but also because they can easily hide and attack in the same turn, granting them an advantage and possibly Sneak Attack in case their target is not engaged in melee combat. Open spaces pretty much ruin that.
While an environment filled with a lot of things can be fun and engaging, especially since rogues are a class that takes advantage of scenarios like that constantly, a big, open room for the boss fight or another type of fight will cut their ability to hide. You can also avoid fights at night since darkness can sometimes be used to achieve the same goal.

4Play With NPCs' Resistances
Cut Their Sneak Attack In Half
Many powerful enemies come with resistanceto slashing, piercing, and bludgeoning attacks, and most rogue weapons fall under the category of slashing or primarily piercing. In other words, if your enemy has resistance against these types, then you’ve just cut their damage in half - literally.
Most monsters with these resistances will only be resistant if the weapon is not magical, but there are cases where these resistances go beyond non-magical weapons. Just be careful not to add this to most monsters because you’ll make the fight harder for all martials, not just the rogue.

3Force Disadvantages On The Rogue
From Proximity To Conditions
Returning to combat, one of the easiest ways to undo Sneak Attack - their greatest damage source - is to ensure they have disadvantage on the attack. Disadvantage completely stops them from triggering it, even if the target is in melee combat with someone else.
You can trigger those by either staying too close or way too far (if the rogue fights with ranged weapons), or you can apply conditions, such as frightened, blinded, restrained, or poisoned. If they are ranged, you can even fall prone to trigger disadvantage - just be sure no melee character will reach you.

2Challenge Their Ability Checks
See What They’re Good At And Increase The Difficulty
Rogues also excel in their skill proficiencies, as they can be proficient with a lot of them and even add expertise to some, being efficient characters in whatever they focus on, such as stealth and sleight of hand, among many other options.
You can increase the difficultyof these checks when it makes sense to do so. It can go from magical traps that are harder to detect to doors that are particularly difficult to open. You can even use magical traps or locks that just can’t be interacted with for those who can’t use the correct spells, creating teamwork opportunities between the rogue and the party’s spellcaster.

1Don’t Rely On Spells With Dexterity Saving Throws
They Can Escape It Completely
Spells are one of the most efficient ways to attack the players, sometimesmost of all of them with the same spell.And out of all the spells in the game, most of them force your target into dexterity saving throws, which is a very good thing for your rogue, especially at high levels.
Not only do they have a high dexterity most of the time, allowing them to pass these checks, but eventually, they get evasion, which allows them to take half damage on failures and no damage on success. The easy fix here is to just use spells that don’t rely on dexterity since evasion only applies to them. Force their constitution, wisdom, strength, or whatever ability score they dumped.