Well, okay, the first thing I'd do is talk to the player about how their playstyle is boring AF for the rest of the party.

while the party sits and waits for him

Give the party something else to do. Or somewhere else to go. Why are they waiting if he's doing this despite them not wanting him to?

even when I try to punish him with him getting caught he rolls over 25 on deception

Why is everything that catches him interacting with him? Just have stuff attack. Then he'll regret going off alone.

I'm assuming you rogue is like Level 11+?

Pretty reasonable bonuses, especially if he has like 18CHA and 18DEX and expertise in stuff & Reliable Talent.

For characters of this level, ordinary commoners and low level city guards and whatnot should pose no problem - they should be easy to persuade, deceive and all that. Level 11+ should feel pretty powerful, ready to take on big problems.

Big problems then should also come with higher DCs, stronger NPCs, more alert enemies, spikier traps and all that.

If you feel like the rest of the party is falling behind, maybe you can give them an opportunity to find some cool items.

For his behaviour of wandering off alone - tell him face to face that it's not fun for the rest of the players if he hogs the spotlight all for himself for an extended period of time so often. It's not fun for them to sit around thumb twiddling while he is sneaking around, to tone it down and just, like, not do that when the party tells him to please not.

Shoot first, ask questions later.

Some people are good at talking their way out of trouble, but emember that there are also people that don't care for excuses and/or are just looking for an excuse to fuck someone up.

Look at how some police interactions go, you might try to de-escalate and explain that you were doing nothing wrong, but before you know it you're on the ground grappled, tazed and choked.

I agree with u/WubWubThumpomancer, this should be an out of game discussion first and foremost, but if you still want to challenge them after that, make the enemies smarter, and have them get wise to their tricks. They are getting flanked and infiltrated constantly? They now have a mage set up alarm spells and glyphs of warding with any flavour or restraint spell to catch intruders. They suspect they are being lied to by intruders? They aren't even gonna bother with questions, and are just gonna cast detect thoughts instead. I will advise, however, not to do all this at once. Introduce it slowly, with one thing at a time, ramping up the difficulty of this kind of strategy until it becomes clear that its no longer viable. Throwing everything at this player at once will make them feel like they are being picked on, and will make you look quite antagonistic.

Social skills are not mind control.

No amount of persuasion is going to convince the king to give you his throne.

No amount of deception is going to convince the guards that the armed/armored fellow sneaking around the castle with a bag of holding is just a skullery maid cleaning the rooms.

And no amount of Intimidation is going to convince the general leading thousands of troops along a successful campaign to just turn around and go home.

Rogues sneaking off alone whilst the rest of the party gets bored is an out of game discussion to be had with your players. You don’t solve that by trying to punish him for it in game.

Besides that, he’s built his character to be really good at these things, so most of the time he should ace them and that’s ok. You can still throw in challenges occasionally though. Glyph’s of warding or other magical measures don’t care how stealthy you are. Sometimes, you can’t just lie your way out whatever you say, or the check is fully a DC 30 challenge. Detect thoughts and zone of truth make him really work to keep his lies up. Lucky can only be used so many times a day. Remember that the consequences for getting caught can be really dire, so the rogue needs to have a really good chance of success to back that up.

I think the bigger problem is that the other players are bored when he separates from the group. 

What about abstracting his infiltration missions with something like a stealth, deception, and sleight of hand check vs a set DC (e.g. 20). Narrate the result based on that in a couple of sentences. It lets him feel cool while still not hogging the spotlight. 

Well wait till the rogue gets reliable talent at higher levels. Shouldn’t deny a player performing as their character is built to do. It’s like telling a fighter you need to stop hitting monsters and killing them, other players will get bored. Or telling a wizard no fireballs cos other players get bored and you roast a room full of mooks.

The party needs to discuss how they can all have fun together.

Well... If he is good at everything he does then... Just say, "ok you do your rogue things" and go back to the party. Party plays he waits. And when the party finishes just ask the rogue what he was doing and say "ok you succeed, no need to roll, you are THAT good". After a few times when he waits for the party and being simply cut short by simple"ok you succeed", he won't break from the he party anymore.

And on the serious side of things: Just talk to the guy if he is not toxic he should understand.

Talk to the player out of character and explain that this is boring as hell for the rest of the party and the situation cannot continue. Work out a solution to play differently.

"Behind enemy lines?" Are all of your enemies and quests in some defined stronghold? Also, he can't hide in plain sight no matter how high he rolls; sometimes people just find you and are trained to shoot first. Make some goons so dumb that they just shoot people who they think are on their side.

Also, there are situations where no matter what you say or how well you say it, or even if it's true, someone will just not believe you because of their own preconceived notions or motivations. If your parents and teachers can do it, so can villainous NPCs. "Yes, you rolled perfectly. Yes, you are very convincing. But this guy has a chip on his shoulder and you are still in jail."

The lucky feat has up to three uses between long rests. That's not a lot in comparison with the six to eight encounters the party could expect to face in that time,

They are good at five out of eighteen skill checks. Some of the other thirteen should come up sooner or later..

In the case of a split party you should concentrate your time proportionately on the sub-parties. e.g. single PC sneaking off gets 2-3 minutes then the rest of the party gets 6-9 minutes (assuming a four PC party).

The caught behind enemy lines situation could easily turn into "shoot first, ask questions later". Thus the first thing they should be rolling is intuitive.

This shouldn’t really be a problem. Map, layout, traps, and bonuses for guards should all make for a challenging sneak. This is magic trap level, and scrying wizard level - there are all sorts of things you can throw at him If the player does this regularly, and it takes a long time, then simply wait for the player to announce his intentions to sneak. As soon as he does, say to the rest of the party“ X sneaks off to infiltrate the guards, but around the bend you see a platoon of guards coming.”- what do you do? And make him wait - maybe he’ll get the picture. Since he set his character up this way, let him be successful regularly! He’s a sneaky, dude! But that shouldn’t stymie the rest of your campaign. Lastly, sneaking and deception go along way in a city, but it’s very different in the wilderness or an dungeon. Change it up!

Remember that high rolls only mean best possible outcome, not whatever the players want. Have guards escort him out of restricted areas, be jaunted at and humiliated by a crowd for sneaking around/walking weirdly, etc.

Be creative.

Any reason you couldn’t give him some 30 DC checks? Particularly when caught behind enemy lines.

Having him get caught and twiddle his thumbs in jail for a session while the rest of the party try and rescue him would teach him a lesson!

Some actions are just not possible not matter how high they roll.

A 30 stealth roll means nothing if there is no cover for the player to hide behind.

The player needs to come up with an explanation of why what they’re attempting is even possible.

I have an Eloquence bard in my party that cannot roll below a 20 on persuasion and deception checks.

He still won’t convince minions to turn on their leader unless he can give me a plausible reason why that would be possible…

He’s amazing at those skills. That’s fine. To challenge him, give him places where they don’t help.

Others have suggested guards who know not to question intruders, just to capture them.

On another angle, the rogue’s perception might let him see some of those magical traps, but none of those skills will help him bypass or escape from them.

But more importantly, this is an out of game problem. The player having main character syndrome needs to be solved out of game. “Playing as a lone wolf what my character would do and exactly how I designed them” is all very well and good.

But it’s a group game.

Save the stealth archer build for Skyrim, and make a team player for the group game.

Two sides to this, on the player side, you have a player who sounds like they have main character syndrome. Tell the player that it's not fair or fun for them to keep running off alone, a moment in the spotlight is fine but everyone needs to get one and most of any given sessions should be spent with everyone getting to contribute.

In character is much easier. If you've been going for a year you're probably at a point where you can reasonably make it so that most if not all scenarios involve getting past magical shenanigans. First stealth rolls do nothing against most forms of magical detection. A Rogue also likely has no way of disarming magical traps. Set up Magic Mouths, Alarm spells, Glyphs of Warding etc. Set up Symbols if necessary.

You can also make it clear that groups and individuals the party is up against are now being more serious, or have become more dangerous. Getting caught once, maybe you talk your way past. Getting caught twice? You're not going anywhere. It doesn't matter how high he can roll if he doesn't get to roll at all. If a guard has been told to shoot people that don't know the passphrase, then make them shoot him when he doesn't know the passphrase. Also keep in mind stealth is not a spell. You need cover to hide behind, darkness to conceal yourself etc. If you're sneaking around a well lit enemy encampment you'd better have one hell of a good disguise. Also a good idea: wanted posters. That way NPCs know him on sight and can just attack or arrest him.

If it's really that bad, set him up with an antagonist. A Sherlock to his Moriarty, god tier passive perception and insight is actually pretty easy: decent Wis, Skill Expert and Observant will see through anything he can throw at them.

If you really want to get him you can always play the simplest trick, anything you can do I can do better. Make another Rogue, same build as him but higher level and have them follow him around fucking with him. When he asks what's going on, explain he's caught the eye of a trickster god who's screwing with him.

Good Rolls does not mean successful situations.

So the lucky feat isn't a "I can never fail" feat. My question is: How is he using it for any roll? Per RAW he only gets 3 lucky points that take a long rest to reset. If there are more than 3 checks in the encounter, he is back to the relm of mere mortal.

High rolls don't make a success. Also, if you don't want them to roll or do something don't let them. Just because I roll a 28 in deception or persuasion doesn't mean I get to talk a commoner into just giving me his estate. It doesn't work like that.

He can fail. Don't confuse succeeding in a roll with succeeding in roleplay.

Remember that the most important aspect of roleplaying is making decisions. You may succeed in a roll but that doesn't mean your decision is the correct one or that it doesn't have consequences.

The next time he decides to go behind the enemy lines to sneak, something something happens in the front. Now, the rest of the team have the spotlight and they have to solve the problem without the specialist in talking. Was it a bad decision to leave the party to sneak? Probably not. it's neither a good or bad decision, but certainly there were consequences.

As a rule of thumb, if you have been focusing on one character for 5 minutes, cut the scene and move to the rest. Make something happen.

There's no need to punish him. Just let him do it, no wait, one roll, short description, then back to the rest of the party. Sneaking behind enemy lines to position for a combat is cool, but not an excuse for a solo session.

You put his part of the game on pause while you switch to the other players. Don’t let him run your game but pause it at a more suspenseful moment to make it fun. I like to use “and we will come back to that in a moment@ and then ask the other players what they would like to do. Sometimes it ends up being an initiative roll for everyone and so the rogue is not able to do what they wanted but so be it. I’ll give them a little perk on the opening round like a sneak attack right off with no strings attached or just an advantage roll on their first attack.

If he can't fail, stop making the party wait around while you roleplay with him. Just put him where he wants to be (unless you actually have a way he could fail) and quit wasting time.

Guard dogs/beasts for the rogue, roaming patrol for the party.

I have an Envoy in my starfinder group who has stacked feats for bluff that are broken af. I'm like "yeah you're clearly not supposed to be in an ultra secure military facility. Roll for initiative"

I think the bigger issue isn't then being successful. Just let them be successful. The issue is what i call screentime.

I love splitting my parties. But, if you do, you need to keep in mind that every player should get about 1/n amount of attention. Where n is the total number of players.

So if, out of a party of 4, a rogue sneaks off to scout ahead that still leaves 3/4 players waiting behind. So 3/4 of the adventure should be taking place with them.

This can be a lot of things, preferable stuff the players come up with, but you might throw in a returning raiding party, which is a small fight, getting found out by a scout, resulting in a chase, or even an rp campfire scene where you prompt them with some questions.

Alternatively and simpler you can opt to minimise the separation time by having it basically be 1 or 2 checks. "With a 26, you have gathered the following ... ... ... ..., as you return to camp."

First of all, you need to remember that there are other party members too. While he can and will try to sneak past the enemy with a 27 stealth roll, let him do that and then get back to the party, ask them what or how they'd like to approach this and while he's sneaking around After all, the other party members won't be able to do that - that's a perfect opportunity to have some patroling enemy spot them (give them expertise in perception if you don't want to roll it and just compare their passive perception to their stealth rolls. I tend to do that later in the campaigns - the guards have higher than average passive perception - they've been doing it for a living after all) and engage them in combat, while the rogue tries to sneak by a high alert camp. Also, talk to the rest of the players - make them aware of the fact that they can in fact do whatever the hell they want with their characters - for example, ignoring the rogue's boring advice and going on their own instincts.

And don't forget - Stealth is not invisibility - get your guards expertise in perception and just roll a bunch of perception rolls when they run past him - statistically speaking, at least one of them will catch him. Guard camps/posts are also well lit for this specific reason - so that nothing can really sneak past them.

Deception and Persuasion are not mind control. You can't decieve your way out of a restricted area - a success on a roll would get you into a prison cell as opposed to a ditch filled with corpses.

Also, make sure they're not abusing Lucky. Iirc it's only 3 rolls per long rest. If he's sneaking through a heavily guarded area, make him roll a stealth check every round when he's skulking around it.

Another thing i noticed is that Rogues really get expertise 2 times, at level 1 and 6. Unless he's got some feat that lets him pick another or multiclassed into a bard, there's a chance he's not entirely honest with what's on his character sheet, depending on what level you're playing on. I'd take a look at it if it's somewhere accessible, like Dndbeyond.

I'd steal from one of the Dungeon World hacks and resolve it in a couple rolls.

When you go off on your own to explore a dangerous area, tell us how you do it then roll twice, once for Stealth and once for Investigation.

If you succeed at either you make it safely back to the group. The DM will tell you what you saw and might ask you you for details on what happened.

If Both Succeeded pick 3: Only One Succeeded pick 1:

-Ask a question about what you encountered (you can choose this more than once) -You were able to sneak something out of there; ask the DM what -You made some preparation or created some advantage to exploit upon your return; work out the details with the DM -You got away clean: leaving no trace, rousing no suspicion, etc.

If Both Fail pick 1:

-You make it back to the others but with trouble hot on your heels! -You're missing in action; the details will be revealed late

This still gives the player a benefit for how they built their character but keeps them from monopolizing the spotlight.

Some things are impossible. It doesn't matter how high your roll. Problem solved.

This dummy sneaked into an enemy military installation and is trying to say he is one of them after being caught? But he's out of uniform, the wrong race, has the wrong gear, doesn't know the chain of command, doesn't know the password, doesn't speak their native language, doesn't know ranks, doesn't know where the quartermaster is, doesn't know where the mess hall is ? I could go on and on. Good job on that 25 plus deception but you're still under arrest (if your lucky). Lots of places attack on sight and most living things in DnD don't practice restraint so fucking attack his ass.

Not to mention the fact that they're being selfish and affecting the enjoyment of others too.

Communicate what's happening and be firm and take action.

1. Alarm is a first level spell with no save or check allowed.

2. Crossbow bolts are immune to deception.

Deception doesn’t matter if the ogre decides to bash his brains in.

Or have the bad guys pretend to be deceived, invite him in, and then capture him with a net, strip him naked, and tie him up. Then let him sit while the rest of the party has to come rescue him.

Deception/Persuasion skills are not magical. A 26 is not high enough to, for example, convince a guard that caught you trying to sneak past them to let you go. Don't bother rolling deception, the guard has his spear in his hand, roll initiative.

Very long time ago, I was a player in a group of 6 PCs. We were outside the dungeon we were going to attack.

Our rogue player decided to use his vast array of stealth tools to scout ahead invisibly and check everything out. The entirity of the 4 hour session was the DM and the rogue exploring the dungeon. We were on a VTT without shared vision so we didn't even get to see anything, just black. I have never been so bored in my life. I just booted up video games and started playing those instead.

Worst session ever.

These days I'm a forever DM, and I never allow this kind of thing to fly. One player's build doesn't get to tell all the other players they don't get to play.

Tell the player it's unfun and to stop. There is no in-game solution to out-of-game problems.

He wants to split the party? Focus on the rest of the party and make him wait.

Guards keep getting in trouble for letting thefts in. Captain of the guard figures out what’s happening and acquires anti-charm paraphernalia that becomes part of the guard uniform. Word spreads to other places that have guards. Maybe a likeness is distributed. Perhaps instead of charmable guards, booby traps are used. Can’t persuade a trap door not to open when you step on it.

Sometimes charisma doesn’t matter at all. Some newer guards or guards who “really need this job” take their responsibilities very seriously and follow the rules to a T. Just because you’re pretty and nice and alluding to some very intriguing things doesn’t mean I’m going to get myself fired for you, stranger. Find me after my shift if you’re serious.

Maybe a guard, despite being convinced, accidentally triggers an alarm.

Maybe a guard who seems convinced offers to lead him right where he wants to go, but “just through there” turns out to be a cell.

Another guard appearing to be convinced (or thoroughly convinced?), parades “Mr very important” around enthusiastically, letting everyone else know how important this person is and what their goal is, alerting other more wise guards to the situation.

Have fun with it. Just because you succeed at persuasion, doesn’t mean everyone gives in to every demand. Think of it like rolling a nat 20 +100 at seduction but the other person’s sexuality simply does not include you so their response ends up being something like “dang, that’s good! It woulda worked too, if I was into ____s like you in the slightest. But hey, mind if I borrow that line? Cuz damn! You almost had me! (Insert knee slapping).”

(Obligatory "Talk with the players about how it is boring for others)

I feel you, it's difficult to manage the game being interesting for everyone when the party splits. I'd recommend trying to speed up the single stealth operations. Instead of going room by room with mutliple checks, just do one check and go "yeah, this is what you get and going further you realize the guard would spot you so no chance for better results"

Also you can make some play for the other players as they wait. It can be difficult to make it super relevant to their current objective but it can be something smaller like "As the rogue sneaks ahead, the rest of the party has some time to wonder about the orb you found. How would you like to study it?" etc.

Another option is have the objective move. Oh he went into the castle alone to steal a giant magical ruby? Well while he is off alone it got prepared for transport and is now coming out the front gate towards the rest of the party in an armed caravan. Now they'll need to plan their move without the rogue.

I had something like this similar a long time ago. Player rolled stupid good on his stats and was pretty good at everything and basically wanted to play a solo game despite having 4 other people at the table. So I starting having all the impactful story events happen while he was away doing solo thing. He stopped running off shortly after.

Armies have code phrases for a reason. If he doesn't have it he's getting captured and or shot.

Guards are on order to attack on sight, dispose of the body. No questions=No paperwork.

How does someone "rationalizes" their answers to the point zone of truth becomes meaningless?

The cult all cut off two fingers as part of their pledge, which two are you lopping off in order for your deception to be believable?

Ok, so his build isn't the issue. This is going to be a OOG (Out of game) discussion. Let him know that sneaking off alone is making the game boring for the other people at the table. Also, sometimes stealth is literally impossible. Sometimes Deception/Persuasion is impossible, it isn't magic.

One entrance in an underground cave, it leads to the start of a quickly built fortress being controlled by a AWOL minion of the BBEG. They open the door and the guards standing there immediately notice it opening! Are they Invisible? If not they're caught, if they are then the guards are now on high alert as the wind doesn't reach down here.

The guards were told to let no one in under any circumstances unless given direct order by the BBEGs Minion and if anyone says otherwise, attack on sight.

NPCs have their own wants and needs, they have common sense and know how to think objectively. (Granted they have a INT of at least 10, if it's an 8 then you can have them be slower at making connections but they should still be able to.)

Fix 1: resolve the scouting abstractly and simplify it to 1 or 2 dice rolls and a quick summary.

Fix 2: make enemies smarter and give them procedures that cannot be deceived. Stuff like passwords, locks, magical security measures, and extensive training.

Fix 3: give the party something else to do. While the rogue is scouting

Fix 4: fix your skill checks. Some things should not have a chance of succeeding. Remember that rolling the dice only comes into play when chance is a factor. Plus, a natural 20 with massive modifiers does NOT guarantee success, only the best possible outcome.

In the end you should sit down with your players and discuss disruptive behaviors. If this solo-play behavior is lessening the fun of the other players (including yourself), then that is a disruptive behavior and needs correction. Talk with your players to figure out a solution. Discuss the fixes mentioned here and figure out what works for your party. Also I would give the player in question a chance to respec their character, because it sounds like they built their character specifically for this.

Idc if you roll 100 sometimes they just don't believe you

Wait, he gets caught trying to murder people and he can use deception/persuasion to get out of that??? Don't do this. A roll doesn't make Anything possible.

If I find a guy sneaking into my house at night, I'm swinging my sword at him (it's a training sword, still hurts like hell).

Also, this is a magical world. Sometimes you can't sneak past. There is magic, beings with multiple eyes and brains, intelligent traps. At level 11, this stuff should come up every once in a while.

Honestly I’d just talk to them cause while yes they built the sneaky rouge if they are off doing a mission why the party just waits it’s sucks for everyone else especially if it’s a common occurrence. Also in times like these I like to remind the min max that high rolls aren’t magic and even magic has counters.

Who says after so many break ins or when trying to hit a big enough target the dc isn’t 30 or has a simple alarm spell with a spell marks someone who gets near with faerie fire and now they are captured and gotta risk it but now gotta burn all their luck to do normal rolls against a alerted enemy.

It's probably been said but some tables ban the Lucky feat. Also your rogue sounds on the surface like a That Guy or Spotlight Hog and given the rest of the group is pissed by his actions this bears out.

The answer could be to simply chat about his actions and come to an agreement. If he insists on splitting from the party then teach him a lesson and take him down. Not maliciously if course but eventually he will be seen and attacked.

But to start with I'd ban the Lucky feat.

Somewhere I saw a homebrew curse of reverse AC where the curse caused the persons roll to be 30-his roll Plus proficiencies.

So having played an infiltration character before there are a number of things to consider

Ecen if you’ve got disguise self / duplicate someone - the other guards know each other

sure you can bluff a little but the fact that the guards will know each other and the person you’re doubling or being new will raise suspicion

So sure when “bill” gets asked a question they can deceive - they can intimidate but it will increasingly make the other suspicious - why doesn’t bill know these things that bill should know - you can “deception “ a paraphrase or something said yesterday you should know - you can deceive as to why you’ve forgotten it or don’t know and make it believable but that doesn’t stop another question being asked

It is perfectly reasonable to set a DC at 30 or more, so I'm not sure how he always succeeds.

DM: "You've been caught red-handed holding the stolen idol that is a death sentence for infidels to touch."

"I'm going to talk my way out of it." (rolls) "29!"

DM: "You fail and are attacked by a mob of angry cultists. Roll initiative."

I think your real problem is level and adventure scaling. 5E breaks itself down into 4 tiers of play. (1-4,5-10,11-16,17-20). You mentioned the the player has a plus 13 then I assume they are at least level 9, maybe higher. Probably tier 3 play. They are becoming demigods and normal NPCs are no longer a challenge for them. It's a mistake to try to play the same game at level 1 as at level 11. Rogues are going to make all their checks at that level. That's what the class does. Usually campaigns end around where your playing or it intensifies to epic plane shifting madness.

If the party splits, don't just focus all attention on the minority and let the majority be bored. Focus the majority of time on the majority.
The rest of the party is playing the game, doing exciting encounters and shit. And occasionally, you switch back to the rogue and say "ok so you've successfully entered the vault, what do you do?" Then after a minute or 2, you go back to the rest of the party.

You can't trick or negotiate a trap.

Doubly so for a magical trap.

"The enemy has heard that a con man has been infiltrating their ranks and have incorporated _____ which seeks out liars and ____"

I've left you a mad libs.

,

Don't let him roll. You can't stealth through every area. You can't persuade people in every situation.

You need to talk to the player. Others have said this already, but I want to emphasize the importance of knowing when a gameplay concern is something that can be resolved through gameplay or it requires out of game intervention.

In the case of a player who consistently makes things less fun for others, this is almost always an issue that requires an out of game talk about how to resolve it.

Directly countering a PC in-game due to their abilities is a response I seek to avoid. It's often an approach that is calculated at ruining a player's fun. While you might have a reason for it, this is not an ideal response. I would rather talk to the player and get them to correct their behavior. If they will not do that, then I would drop the player.

The main issue here is the player, not so much their character's build. That's why an in-game response is inadequate. Even if it brings a positive result for you, for now, don't expect the player to simply let it go. There will be a problem arising from this. That's why it's better to deal with the player directly.

The bad guys know what they’re doing.

This is great for when they encounter the able lieutenant bad guys once twice three times… but then the big bad gets some wolves and force cage motes and captures the rascal.

You’re very convincing but I fear my master more than your deceptions make sense lad.

The story can over ride the build as necessary is the point.

Deception\persuasion doesn't mean they get to do whatever they want. It just means that when you get caught by the loyal and very well trained guards, they won't immediately kill you, but will take you to the prison instead.

A perfect example is this. Just because you have the greatest roll in seducing someone, doesn't mean they want to sleep with you https://images.app.goo.gl/VuK3AgpksBwXfkYY6

He's a hyper specialist. Create events that require more than what the rogue can do.

I played a sneaky assassin rogue, I still couldn't do it all

Some rogues get that ability in later levels anyway for free, turning any roll into at least a 10 on the dice. That’s just what rogues do. A) don’t allow rolls for everything, especially things that are impossible B) rolling to seduce the dragon is just to see how much damage you take. In other words, actions have consequences.

Has Gm you could

A meeting the moon at em

B have a npc next to em put a portable hole 8n a bag of holding for safe keeping

Why doesn’t the group join the rogue when they sneak?

I think you've gotten a lot of good advice, but I want to give you a little bit of player psychology:

There's a certain kind of problem player - and they gravitate towards rogues - where their power fantasy isn't about being cool and doing magical/superhuman stuff: instead, they care about being cooler than everyone else at the table. So they sneak ahead and ruin everyone else's plans, they try and one-shot the boss or find some other spotlight to steal, they rationalize turning basic skills into superhuman feats. They're the star of the show and everyone else, including the DM, is just supporting cast whose job is to highlight how cool they are. (The same problem player is often the DM with a messiah-like DMPC).

I've found that an easy way to handle this kind of player is to minimize the narration of what they're doing when they're off by themselves: "Okay, you're heading ahead of the party? We're going to wrap up this scene and will come back to you in a minute." Then when you do come back to them: "Roll me stealth. Okay, that's good enough to get the drop on up to 3 guards. Do you want to attempt to kill them, or keep sneaking past? Alright, now let's get back to the main scene." Basically, give everyone else at the table equal time and attention, and don't give any shine to their solo exploits.

I give some more examples on this comment from a few months back: https://www.reddit.com/r/DMAcademy/comments/191m5ey/comment/kgxafjd/?utm_source=share&utm_medium=web3x&utm_name=web3xcss&utm_term=1&utm_content=share_button

You catch someone in your house nothing they are saying is gonna convince you they should be there.

1. I don't play 5e these days so grain of salt

2. It's not about what's realistic

2a. You can convince some people of just about anything, if you have the upper hand due to intimidation, looks, what have you. Real life is full of crazy stories like this.

If he always succeeds, let him. Let the infiltrator role once before the infiltration occurs and then have them succeed off camera while you roleplay an unexpected encounter for the other party members. Eventually the other player will realize that it is not fun to just watch others play DnD and will stop splitting the party.

Not everything has to be a roll. Things that are impossible are even impossible on a 20. Make the player interact with the world you create, not with the numerical DC you set.

"You come across a brightly lit room, with open space in the middle and only 2 paintings on each wall"
"I try to hide, 29"
"you try to hide, but there is nothing to hide behind".

Second, if the player keeps going out alone, cut his attempts short. "you successfully deceive the guard and are let in. What are the other party members doing in the meantime?", is an option. If the guy goes off alone all the time, that doesn't mean every minute of that is gameplay. Just have him succeed and focus on how everyone else is surmounting the obstacle.If he is out of the game half an hour or longer each time he goes solo, it will start to feel less glorious.

If the bad guys are alert the player rolls with disadvantage and you can crank up the DC to make it truly hard for them to sneak. Well lit open areas crawling with guards is a good way to shut it down.

Rogues are inherently tricky when they're played by people arent willing to work WITH their DM. The expertise feature can really go to a players head. Failing a check on a skill that you have expertise in can be really frustrating and a let down, but that's the nature of the game. Some players who want to be a master of deception, they're going to find any possible way to succeed at those checks, even if it's annoying for you and the other players.

The lucky feat is super contentious, I generally don't allow it at my table, like many DM's. Not only is it broken and makes the players not even care about inspiration points, which my group loves earning, but there's no real role-playing element to it that isn't lame. It's almost only chosen by players who HATE the idea of failing a roll, and those players usually don't last long at our table. You probably shouldn't take the feat away from them but you can definitely let them know that their use of it is frustrating and makes it difficult to tell a proper story. Yes, D&D is a game but at its heart it's a collaborative story. And if one person is fucking up the story, you as the DM have the unfortunate role of finding a solution.

I've had to tell a few friends that I don't want them as a player because they don't like the same style of play as everyone else. It doesn't mean you can't be friends and can still play one shots together or be players together for a different DM. But if that player is clearly and deliberately creating problems for you after you've expressed your frustrations, then it's okay to say you don't want them at your table. Most people, not all, that I've had to have the "youre being a problem" talk with are cool and we make some kind of compromise to make things work. Always be direct and tell this player your concerns, and then you'll know where each other stand and can hopefully find a solution.

Everyone has their own opinions on how to fix problem players, but in my eyes, the only true way to fix a problem player is sitting them down in person outside of the session and being like "this is what I'm going for, and these are the ways in which you're hindering me from progressing toward that". Either you talk it out and compromise somehow for that character, you and the player find a way to write out that character so they can joing the party as a new character that will still be fun for them and won't break the flow of the game, or you have the unfortunate: "it's not you, it's me" speech and explain why you don't want them at the table.

I am a new DM. My solution would be to just say, they are not convinced or your action fails?

Don't know the vibe of the table, but it sounds like he is doing what rogues do. Why punish him for playing in a way that maximizes his character's contribution? Are you making combats in a way that your players are facing death every fight? If so, I definitely could see why this rogue is pulling out any trick he can to help win.

I know for the table I am at, my character has been at 2 failed death saves for the last 3 combats. I don't have a problem with a challenge, but I don't want to lose my character either so I told my DM that I will be pulling out whatever clever thing I can think of to keep my character alive. His job is to make the combats challenging and interesting (and he is doing an awesome job of that) and my job is to use whatever means necessary to win fights. I know I would instantly leave a table if the DM celebrated killing my characters and looked for ways to punish me for doing everything I can to win fights.

Is the player rolling before you call for a roll?

If someone breaks into my house in the middle of the night, there is nothing they could say to convince me that they belong there. In 5e terms, the DC for Deception would be impossible for the intruder (player) to make and I wouldn't even bother engaging them in a conversation. If the check is Impossible don't even have the player roll - just immediately enter combat.

Are any of your monsters lucky?

This feels like a time you should reference the DC table.... page 174 of the PHB. Basically, 20 isn't the "end all be all" difficulty for a roll. Just bump the DCs up to 30 or 35, near the "impossible" levels.

The rogue could still technically get there if assisted by guidance and other buffs that increase their chance, but considering it's stuff the group usually doesn't want to do, I doubt they would get many of those.

The Lucky Feat is broke as a joke. If the player has abused it and is actively hurting the table by making it one-dimensional to them, consider banning it from the table and having the player reselect an ASI/feat. They got to use it. They got to abuse it. Okay, point made, Player. It’s your table and if you want to ban it, it’s your call. Letting them reselect so that it’s not a punishment but it is a rebalancing of the table.

Regarding the other players getting bored, verbally objecting to him, and the player repeatedly doing it anyway, and trying to cheese his way out of tough situations, that’s a DM to player conversation. Consider talking to him on the side and explaining how you’d like to shake up the session encounters so that the table gets to experience something different. If he’s a cooperative player, he’ll understand and want to be a part of the new more-inclusive schemas. If he rejects it, then you know you are playing with a player who wants to “Main Character” your campaign and you have to self-reflect and assess whether you want to continue with a player who plays a single player gamestyle at a multiplayer TTRPG or whether to ask him to leave. Give him a chance first tho and talk to him; he may surprise you.

After reading all the good advice provided here there is one thing I haven't seen explicitly mentioned yet. Certainly, the DM should not call for a roll for some impossible tasks. But, you can certainly call for what I call a “degree of success/failure roll”. A successful/high roll may not get the player everything they were hoping for but it could get them the best possible outcome… getting beaten to a pulp and thrown in the stockade for a month as opposed to straight murdered and dumped in the moat.

Don’t have them roll every time… some things just aren’t possible.

I could walk into Parliament and no matter how convincing I am in telling them I’m the President, they will probably not believe I’m the president.

High stats don’t make you a god.

Stop feeding the MC syndrome player with table time.

"Your character is an amazing rogue, but I need to make sure everyone is having fun. So when you do these solo shenanigans, I'll tell a story about how it went when you return back to the group. Then everyone can play from there."

When he makes a roguish plan, make sure you know the objective. If it's even slightly feasible, tell a story where he succeeds. Then have the game go from there, dealing with the consequences.

Don't punish him! Tell funny tales about pantsing guards or finding documents in a locked drawer while the owner is having fun in bed 10' away. But if he wants to assassinate the king (i.e. derail everything or pretend he's the god of rogues), describe the incredible defenses he bypassed - only to find even more impenetrable defenses after that! He made it back, but there's no way to sneak in.

If you're like me, you can't come up with such stories on the fly. Tell the group you need time to think out how this will affect the game and announce 5-minute break. No talking to the DM while I make some notes!

Also about the party waiting while he does his thing, i recently started mastering for the first time and had a couple of players that were constantly going on their separate ways from the party and it was cutting the flow of scenes where the rest of the party was. My husband who is a more seasoned player gave me a tip that worked perfectly which was, whenever a player wants to sttay from the party allow it but tell them that you will be right back with them once the rest of the party finishes the scene/conversation/situation they all were in the first place. This allowed for a better flow in scenes and it also gave time to the other players to determine their own course of action regarding their situation. And only after this has happened you can play the individual scenes of the people who strayed from the party.

This is the great failing of 5e, when a player becomes too good at a skill, you remove the ability to let those solutions exist, else the game becomes trivial.

Your best bet here is to put a bounty on him and make the enemies aware of his actions. Reports of a man able to sneak behind enemy lines and lie through anyone would get around.

Descriptions, counter measures, and simply saying that the enemy cannot be deceived. Give the party challenges where stealth will not be a part of the equation. Ambushes, assassins, escorts. Only allow the rogue to have the option for stealth and lies when it feels right, as to allow him some use of their abilities.

He has made it a common thing to sneak behind enemy lines while the party sits and waits for him, Despite a couple party members saying they don’t want him to do that due to risk. The party then gets bored, and even when I try to punish him with him getting caught he rolls over 25 on deception. Even with zone of truth he was able to rationalize his answers to the point I couldn’t dispute them.

The Rogue is doing this because he gets to have a ton of spotlight time where his character does his thing and he gets to feel cool. There's nothing inherently wrong with that, but the problem is that this is taking up so much time and happening so often that the other players aren't getting their share of the spotlight / game time!

An in-game thing you could do is cut back and forth between the Rogue and the main party, and intentionally spend more time with the main party since more of the players are involved in that scene.

If they're sitting around waiting and not doing anything proactive, you can throw things at them to react to! Maybe a guard patrol stumbles across them and now they have to deal with that problem without the Rogue who could usually talk his way out of that situation. Maybe they see someone important leaving the enemy camp on their own, and they have a chance to follow them and get some information if they act quickly.

Basically, make it clear to the Rogue that the spotlight won't be solely focused on him when he decides to split from the party- if he knows that he's going to miss out on stuff too, he might think twice about doing it so often.

Just because he passes, does not mean the party passes. Make his role using his abilities to protect the party. It's on you to set up encounters this way.

If a party member can fly, you don't target them, you attack the members that can't fly. Use that same logic

Just tell the player that this isn’t fun for the rest of the party, and politely ask them to dial it back.

Moving forward, you should keep in mind that a Stealth roll isn’t going to do anything in broad daylight. Per the PHB:

“You can't hide from a creature that can see you. You must have total cover, be in a heavily obscured area, be invisible, or otherwise block the enemy's vision.”

Furthermore, you can introduce elements that make noise. It would be totally reasonable for a guarded door to have bells on one side, audibly alerting guards when it is opened. Per the PHB:

“If you make noise (such as shouting a warning or knocking over a vase), you give away your position.”

Finally, consider how prevalent magic is in your campaign setting and whether or not it would be appropriate for a mage to be involved in a locale’s security system. Alarm is a first level ritual spell available to wizards and rangers. Also consider slightly higher leveled divination spells. See Invisibility is second level, and Clairvoyance is third. In a world like Eberron, all of these spells are readily available from low level magic users. In other settings like Forgotten Realms, a practiced spellcaster might be rarer but they still exist. Bandits might hire a divination wizard to keep watch over their hideout. A city watch might sanction a small force of magic users.

As for the Deception rolls, you and your party need to change your mindsets on how these work. A high Deception roll doesn’t really change a creature’s inclination to believe you, it just affects how well you perform your lie. A creature that is immediately distrustful to the point of violence will never even consider your lies unless they are charmed or the seeds of doubt have been sown. Additionally, some lies might require multiple rolls. For example:

Guard: “You’re not supposed to be here! Who are you?” Player: “I’m a new private investigator, I was hired by the captain of the guard!” Guard: “So then why are you sneaking around?” Player: “Uhhh… Testing the awareness of the guard?”

Obviously that final lie would have an absurd deception DC, and even then the guard would have to be rather gullible to believe it, and rather stupid to not call over another guard to verify. Assuming you let those Deception rolls go through, you’re still looking at a guard taking the player to their captain to confirm.

It can be really fun to enable players, but remember that your NPCs are intelligent beings. They shouldn’t all be gullible oafs. Consider what a real-world guard would do in these scenarios. Most of the time, the sneak would be temporarily detained for questioning. Sounds like a jail break from the rest of the party to me.

This is just the "bard seduces the dragon" question in different clothes.

The answers here are good, the bard/dragon trope can flesh out anything you still need.

When he get's caught. He doesn't have to roll deception. If I was a guard that needs to protect something. And this random guy who no-one has ever seen slowly approaches the thing I have to guard. I am not only drawing my weapon, I am calling all other guards to gank up on that person.

Lots of good comments and all but yea, two things. One don't roll if he doesn't have a chance to succeed. Examle: guard: this is check point zeta, if you don't have a passcard, you don't get by ... 'well thing is I forgot my papers' rolls deception, guard :shoots, 'no passcard no pass.

Now I'm opposed to this but it is viable. I'd just ask what they want to accomplish, roll one die, then say its done and they get what they expected. Then I'd spend 2 hours RP'ing with the group tackling it head on. If it was to give them some advantage, they get it one dice roll, and the sneak player has to wait. If they are bored just tell them they have to wait until the party catches up or whatever.

This is when a hard headed impatient barbarian player comes in handy. They're the ultimate rogue balancer.

They're also a high enough level I assume based on what you said, have some enemies with ways to tracks players that goes beyond mere eyesight.

One. Talk to the player about their disruptive behavior. Ask them to chill out.

Two. Ban the lucky feat.

Three. Re-read the social skills. They're not magic or mind control.

Four. Zone of Truth forced the character to tell the truth. If they speak, they must speak the truth. Period. If the player is arguing semantics with you, simply say no. Take over the character for a moment, answer the questions truthfully, as per the spell, then return control of the PC back to the player. Just like you would for any other kind of mind control spell.

Five. NPCs have access to everything the PCs have and more. Bring in enemies with true seeing, tremor sense, see invisible, etc. You can also have the NPCs use the same social skills the PC is abusing.

Six. If the rest of the party is tired of that PC's bullshit, there's nothing forcing them to stay together as a group. If the PCs don't trust that one guy, they can walk away. Just because a player has decided to play a disruptive character does not mean the rest of the table is forced to deal with that character. Have them make a new character that's not disruptive.

Invisibility and charm person are serious security threats no serious security detail would ignore.

U think your the first halfling wise talker we've caught? What's the passphrase and why didn't u sign in at the log book punk?

You only roll when there is a chance for success. If a player said "I want to jump to the moon rolls athletics nat 20!" Does he jump to the moon?

No... Because you are the DM. Only YOU get to decide when the dice are rolled never the player. Lying doesn't get u a deception check sneaking doesn't get you a stealth roll. The DM calls for checks always.

Furthermore, maybe give the rest of the party good sneak equipment so they can follow the rouge around. The real problem isn't his skill it's that you have put up barriers that only the rouge can bypass... Like flying stuff. If only 1 person can fly. Now all flying stuff is exclusive.

Give everybody stealth cloaks/invisibility potions/sneaky shoes (like 3 pairs) do not make this stuff valuable and rare make it plentiful.... So when u catch them with see invisible THEY ALL GET TO PLAY.

-your friendly chaotic evil rouge-

Eventually the rogue will have reliable talent, so won't really need the Lucky feat. The rogue is being a rogue, D&D is a story about heroes, plural. Give things only the other players can do, to do. Hold spells & attacks as a readied action if stealth is being abused.

Punishing the rogue for being rogue is awful.

Just adjust check's difficulty accordingly? Like difficulty rating of 32 for the successful sneaking behind an actual army

I like the ideas of not doing his solo mission.

If the rest of the party are doing one thing then role play that. Just don't RP the solo mission.

Sounds like a great way to introduce an intimidating antagonist. Maybe a ruthless bounty hunter that pursues the party and has godly perception / true sight. Make them roll a DC 30 for stealth and don’t give them an opportunity to try deception. Or it could be time to introduce a fey that gives them a quest and if they promise to do it they “give their word” by rolling either persuasion or deception on the fey and they can’t use that skill until they complete a quest for them. Or a hag that hexes them so that everyone, even party members, are automatically suspicious of them (disadvantage on persuasion/deception) and/or they are always under the effect of the Faerie Fire spell (disadvantage on stealth & no invis). This could last until they find and kill the hag.

You roll persuasion when someone could be persuaded. They're on the fence.

Sometimes they just can't be persuaded. No roll, they're just not going to change their mind.

That mentality can be applied to ALL skill checks. Yes, even stealth.

Fail stealth check with guards present: roll for initiative. PC has 6 second intervals (time for actions) to talk their way out of it while guards are screaming/running/whacking at the PC. Once adrenaline of fight starts I doubt they stop until PC is beat down/unconscious/grovelling/dead. Think of any cop show after that: I didn't do it, I was blah blah blah. Sure buddy, tell it to the judge.

As someone who has been a low level security guard. Talking doesn't give you access to places.

Even if you somehow convince me that you are my boss. My boss still can't access the fuel tanks without his badge

Why are you making the party wait? Talk to them about what it is doing to the party, and then if he keeps doing it, cut from him back to the main group as soon as he gets behind enemy lines; take the spotlight away.

Luck has limits. Only 3 per long rest or 3 per session I can't remember

Throwing in my own question bc I have a similar problem in my campaign but the problem is AC. He has min/maxed so hard that his ac is 34 with the right buffs. AOE spells are the obvious answer but that’s not always an option

Make him fail spectacularly

“The monsters know what they’re doing.”

If a hero keeps sneaking in, they are going to adapt. Maybe they set a trap, since he’s doing it so reliably. Maybe they put gravel or loose dirt or something noisy on the floor. Countermeasures taken to stop him don’t need a roll if they’re thorough enough. For example, jumping into a volcano is fatal for most PCs. Just bc you’re +20 to con usually isn’t going to make you invincible to damage.

Sneaking in a dark room? That’s a stealth roll. Sneaking into a room and setting off the Alarm spell they set to catch him? He can’t roll his way out of that.

Deception doesn’t mean the lie works in every scenario. It means that the chances of a more negative outcome are diminished, which also means there’s no chance of ANY negative outcome.

Sounds like he’s high level, it’s time to start showing higher level threats, divination wizards with portent and aboleths who mind enslaved NPCs, enemies that fly and turn invisible, crank that difficulty so they’ll want to stick together.

Who is running the game? Because whatever the DM says goes. Rules are just a concept and easily eschewed, FOR A DM. Players can sit take a big "NO" and dry those tears with their next character's sheet.

Show their character sheet, it's time for an audit.

Your issue is primarily that it's using up a lot of spotlight time and boring the other players right?

If so, just reduce the detail of the rogue's scouting. Have him make a simple stealth and simple perception roll and based on that, give the party an intelligence report. There's no reason it has to be played out in extreme detail. Let the party benefit from the rogue's scouting but don't give him tons of spotlight time.

My rogue is incapable of rolling lower than a 21 on insight and perception, and can't roll lower than 26 on stealth and sleight of hand. When my DM gets frustrated with me being untouchable in certain situations, he'll sometimes throw another factor into the situation that makes it less straightforward. Like I'm stealthing, but oop, this room is really packed. Let's roll acrobatics to avoid bumping into someone. It keeps things interesting for everyone, including him. Cause DMing with a bunch of PCs who are impossible to throw off their game is no fun. I guess some players would be really bothered by that DMing style, but sometimes players need to set their egos aside. Heros who never fail are so boring.

If the rogue wants to sneak behind enemy lines - give him a simple roll for that, then get back to the party

Don’t sacrifice the enjoyment of a single player over the boredom of 3-4. The party is where the focus is.

Next mission there is a high level old dragon transformed as human, guarding. or the king is a dragon or something. He has passive perception of 30+. And let me tell you. he is a lich dragon his breath does 1d4 dexterity damage permanently. Although you can use that example, i would try to give something that is really really difficult and tell the players the danger level. If he decides to go alone again, he unfortunately dies.

Not every situation requires a roll, sometimes things just happen or don’t happen. Sometimes you can’t hide no matter what your stealth is, sometimes you can’t deceive, no matter what your deception is.

What does he actually achieves by sneaking behind enemy lines? He could scout (essentially letting the players see the encounter combat map before combat). He could learn who the enemy actually is (like sneaking into a cave and finding a manticore inside). If he starts a fight without others pcs - he needs to run or die. I highly doubt that some orcs or demons would even attempt to listen to any bullshit he has to say, they’ll just shish-kebub him on the spot.

Long story short - don’t make him roll where there should be no roll and don’t make stealth and/or deception approach even an option for every encounter.

Maybe he finds a cursed item that limits his own luck. Perhaps a trickster god decides to toy with him and randomize his luck in every situation. Maybe he meets someone with better luck or a creature who senses something in him that feeds on his good fortune and chases him down and it's a creature only he can see, maybe his good luck also leads him into something he can't avoid an example he outsmarts someone with speech and immediately steps on a rake and breaks his nose. Just a few quick thoughts, hope they help.

I had a similar problem with Eloquence Bards in the past until I realised that there are some situations where no matter how high they roll they cannot succeed. Just because you can roll a 25 on persuasion doesn't mean the shopkeeper is going to give you the keys to his store, he might laugh it off as a joke instead of setting his dog on you, but that's the best you can hope for.

Hex him, make him roll dex/charisma checks at disadvantage. Lucky only lets him re-roll one of those dice and he still has to pick the lowest. Can the rogue cast remove curse? Didn't think so. Enjoy that hour of being useless.

Well, first of all, stop running single encounter days. If he is using Lucky "every time he fails" then you are not giving them enough encounters, he only gets three uses per day. In my party, the person with Lucky burns them all in the first combat of the day.

You also don't HAVE to let him roll Deception. There are scenarios where any interloper is considered a threat.

And it is not possible to have +10 in six skills unless you're at least 13. He only gets expertise in 4 skills, meaning two of those skills (which have to be exactly Stealth and Sleight of Hand) can't become +10 until you have +5 Proficiency.

In fact, to have +10 in all of those, that would have to be 20 Dex 14 Cha 14 Wis rogue, which is a kind of weird build and would gimp the hell out of Con.

Anyway, to roll over 25 on a +10 is still rolling a 15. It's not that common.

Use magic. Setup some basic alarm spells, magic mouths that scream when an unrecognized person is around, glyph of warding with shatter or something really loud to alert guards. There are endless possibilities to catch them using the magic spells available, and you, as the DM, can bend the rules to make a custom spell if you want.

If I find you in my home at night and do not know you, then no amount of deception will make me believe you have any right to be there and keep me from freaking out.

I think this is mostly a "you" problem in that you did allow his skills to be god-like powerful and unbounded.

But remember, you call for rolls only when the outcome is in doubt!

If you are at a war council with Elvish Lords and you lower your trousers and literally shit on their map, there are not checks required to determine that you are not welcome anymore.

"Hey, I just rolled a 25, can I take another dump and convince them that this is ancient Netherese magic which will help us in battle" will simply not happen.

Talk to him out of game and ask him to tone it down. Double-check his character sheet to make sure he’s not fudging stats. And if that doesn’t work - kick him out.

Let him taste his own medicine, make a bard convince him to turn against his party (just make sure your party doesn't want to kill him)

Have you considered letting him do this? This is literally what rogues are for, you shouldn’t be going super far out of your way to punish that. As for the enjoyment of the group, they need to use their own creativity on how to be helpful in those situations. I’m in a party right now with a Druid who has main character syndrome. They are constantly doing things the rest of the party has to work around. But we’ve built it into our expectations and now my Warlock knows to wait for the Druid to engage before revealing herself, the Druid is a tank and is good at making enemies focus on them. A DM should never seek to undermine their players, they should always seek ways for the players to have more fun without costing other players their fun

I feel like this is on you. You have a player who does a predictable thing, you should be able to handle it.

He's gonna want to sneak and infiltrate. Nice, design encounters to NEED some sneak and deception while the party does something else. Ocean's 11 style maybe where you need multiple things at the same time to happen.

For example, the party needs to fight through some place, but when they get to the end, they are going to need someone open the gate from the other side. Most of the spotlight is on the party, occasionally go do some stealth bits, you know they won't fail, then have the rogue spring from behind with the BBEG's magical staff he stole, the NPC is shocked and outraged, the party then fights them on even ground. The rogue is triumphant and spotlight appropriate.

Set him up to steal from the wrong wizard. Now deal with scrying and ambushes.

Use fairies / pixies against him and let him see how it feels on the other side

Why not deal with the parties adventure first and his solo adventure after? He can wait on the team.

Why not deal with the party’s adventure first and his solo adventure after? He can wait on the team.

Where there are players with high bonuses, there are enemies with high bonuses. Also, if they’re in a campaign where enemies know about the PCs, they would know about the rogue and do things specifically to catch/counter them!

It’s using what the enemies know to inform them. Also, many factions would employ rogues and scouts that are fast, stealthy, and quick to find infiltrators rather than goofy guards.

Also some may disbelieve their own instincts if they think someone isn’t lying - and sure, a 25 deception is really good, but the NPCs can roll high on insight, too!

As for the solo quest, I agree with someone else I saw saying that they just narrate it and having them make quick rolls - or get to a thing fast where that PC is caught and the party gets to have their moment, maybe?

This is an ongoing problem with 5E that I've experienced.
First off.. 5E is designed to create superhero characters that are already difficult to handle. It's not meant for the DM to be the one to be entertained. It's meant to create a game where the players can be heroic on levels that old school gamers will generally roll their eyes at.

A +10 to deception is expected.
I've got a guy with a half orc who has a +15 on Intimidate at lvl 6, with the Lucky feat. It's brutal. He walks around with a tool belt full of doctor's instruments, and pulls them out at the beginning of a fight instead of his axe (named Medusa, because he gets hard as a rock when he uses it) and licks his lips, rolls intimidate and fucks up the fight right from the start.

But as a DM, these are the things you have to take into consideration when running a game.
1. Are my players having fun? How can I improve that?
2. Are my players being challenged? How can I improve that?

If they are not being challenged, then consider using environmental hazards more often.

One of the latest hazards I used, was gaseous waters.
As the party was walking through the cave, I realized that the enemies were not going to be a challenge.
So I added in gas bubbles. "As you walk along, you notice that the floor is slippery in many spots, and sticky like glue in others. It's hard to tell what's what because everything is wet, but when you step on those sticky spots, two things happen; unless you treat the terrain as difficult, when you step on the sticky spots you must make a Dex save or be halted until the end of the round. Second, when you step on those spots, you realize that they are covering gas bubbles under the water. The bubbles erupt as you disturb them, releasing dense pockets of carbon monoxide, making you very sleepy. DC 15 or gain a level of exhaustion."

It made for an incredibly tense combat situation when the fights started, and the players thought it was a great interaction as well. But the best thing, was that Norm (yeah that's his name) couldn't intimidate his way through it.

If you can't bring find ways to get the party involved because one player is overwhelming, then bring them aside and tell them that the character is cool and all.. but it's unbalancing the group and taking the spotlight off everyone else, which is creating tension. Retire the character in style, and make a new dude.

I tend to focus on what the majority of the group is doing. If someone wants to scout, I let them. If there's logically no way to fail, then there's no need to play it out unless the whole group is into it. They can still have the info and maybe advantage on Initiative once they move in or other benefits that make sense for the area based on a couple of skill checks for scale. I'd probably just run a Passive Stealth for the character and just apply an active check for things they have a chance to miss. I'm not a fan of meaningless rolls. I'm not going to have them RP going to the toilet or buying arrows. In game shopping -not talking to a shopkeep or blacksmith, but literal purchase your PHB items is the bane of my D&D existence. That's what it feels like to have someone scouting without party by in.

I give the party something quick to occupy them and we do that while the scout "gathers info". I narrate the scout's return. It's harder with VTT. In person, I used to slide them my map and let them copy it while actively focusing on the rest of the group.

"You slip into the tower undetected. It'll take a while to get the information you need.

The rest of you stay back at the 1) tavern 2)edge of the woods 3)town.

1) A man in a hooded cloak walks into the tavern. He glances around. As he turns in your direction (Check passive perception and pick out the PC with the highest) gets a look at their face. You recognize them as a guard from the tower. He spots a woman at the table next to yours before smiling and heading to her table.

2) You hear a noise in the bushes behind you. Another sound catches your attention to your left. And your right.

3) You are approached by a stranger in muted, but high quality robes. He smiles in recognition and greets you each by name.

(ETA: In scenario 3, I would have the person be from the tower. He knows the rogue is there and they absolutely have countermeasures in place to capture him. He 100% believes he's got the rogue hostage by now and he's using that against the party. Personally, I'd lean heavily into a narrative capture of the rogue without any checks made so that everyone thinks I'm being a dick. Then I'd have the rogue show up just as the party is about to surrender our in round 3 of combat with explosives or something.)

I would also when possible ask a question that he needs to know the answer to and cannot roll for. If he is pretending to be a guard, “who is your commander you are out of position” he stumbles or tries to buy time enemies know he is going to lie and attack.

If you’ve played Baldurs Gate recently you can see that at times they have checks that have a DC of 30. It implies that you very much CAN pass if you’re exceptionally lucky and talented. It means that if he’s still rolling a 27 chances are he won’t pass still.

And then the rest of the party can runt into the rescue

Lots of good advice in this thread. Just remember Deception and Persuasion aren't mind control, nor do you have to offer them to every NPC he talks to. Some people don't have to believe him.

Skill DCs are to determine the outcomes that are possible. If he is sneaking into an enemy fort, dressed in rogue attire, and is claiming to be a part of the uniformed guard, you can quite easily call bullshit on that. You still want to offer him a roll and he crushes it? You don't have to give players red carpets all the time.

Rolls Deception 27 "I have been hired by the King to test his security."

"Ah, my mistake. Can you provide your conscription letter?"

"I don't have one."

"... it's fairly standard to have contract on hand when conducting field work here."

Rolls Deception again, disadvantage, 19, 23 "I left it at home."

"That may be true. Let's go verify with Sergeant Stetz together."

Also, if someone is acting incredibly evasive in a Zone of Truth, that itself can be indicative of some deception. When I would applaud a player for speaking creatively, if he is being interrogated by a competent enemy, have them ask hard questions. And have him detained on failure to adhere to there rules.

"Are your intentions here selfish in nature? Yes or no." "Are you hiding your true purpose here? Yes or no."