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I'm currently running a levels 1 to 20 campaign with my friends, and one of them is a Ninja (Pathfinder's class using the Basic Rogue Template). Functionally it's pretty much the same, and the thing is that, being a group that really enjoys combat encounters, he always finds himself having a hard time because at least I'm making stealth dificult to use in combat.

My players are not very tactical and like to run directly into encounters, and, following that logic, a character (at least I understand it that way) can't just roll Stealth and pretend to disappear to then use a Stealth Attack since enemies are aware of player positions most of the time.

That's a mistake on their part, however, they've also told me I don't give the stealthy player enough opportunities to hide. Most of our encounters have been on places where there are interesting features they can use at their advantage, but I rarely place stuff to hide since I am constantly discussing with the Ninja that he's just wasting turn on hiding when he can flank with an ally to gain the sneak attack bonus.

I really get bored with stealth elements, and I am personally not very good at running them, since at least for me they're pointless when the characters can just charge into the action and he's the only stealth loving guy there. He's a very good friend of mine and does his job as a ninja, and sometimes my players have asked me to think of more situations where he can have fun as well, but it's really hard for me to include things like this regularly.

Any ideas on how I can balance action and stealth without consuming too many rounds on doing so? That is what kills the fun for me - the character runs away, make stealth rolls, remain hidden, and suddenly attacks when he could gain the same bonus in one round.

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Stealth is fun.

Shadowdancer may be one of the most popular Prestige Classes in 3.5e, and that is solely due to the Hide in Plain Sight feat. Many players enjoy the thought of sneaking invisibly to the enemy and rolling insane backstab/sneak attack damage.

Unfortunately, stealth in D&D is not always that fun.

Now, the backstab part is awesome, and that's why most stealth players enjoy it. The problem is that the D&D mechanics as they are played out in most campaigns do not make much of stealth beyond a canned skill challenge. By looking at some good stealth games for the computer, such as Dishonored or Assassin's Creed, we can take some tips and add them to our campaigns.

Objectives

This is the biggest change that a DM has to foster in his campaign. As mentioned before, the objective of stealth is almost always just to get in some extra sneak attack damage. Stealth gets boring when, in the end, it's only about combat. There is nothing wrong with sneak attacks, of course. Some of the most memorable moments in my campaigns have been sneak attacks (double crit + 4x backstab damage FTW?), but stealth needs variety.

The purpose of stealth is to remain undetected. Let stealth be a tool for defeating encounters. If the players successfully sneak around an entire group of hobgoblins, give them full XP as if they had beaten the fight. And don't just stop there. If you want great stealth encounters, turn it into a real challenge like Dishonored does. Make enemies move around somewhat unpredictably. Have your players use distractions, or find opportunities to pick off the enemy one at a time. Give them bonus XP or a better reputation for being able to complete encounters without bloodshed, similar to Dishonored. Also like Dishonored, make a few combat encounters really dangerous if you rush right into them, and be sure to make that fairly clear through in-game information.

Environment

The world is bigger than a grid. Description helps. Open up the terrain for movement, like Assassin's Creed. Let them sneak past the royal guard by balancing across the rafters of the great hall or by sneaking over the rooftops to bypass the thugs waiting for them in the street. Think in 3D even though the grid is 2D.

Light is a huge factor for stealth in a lot of games, such as Amnesia: The Dark Descent. It ought to be very important in D&D as well, what with all the torches, lanterns, and magical lights often found in its environments. Have players make strategic use of light. One campaign, my players doused a torch while the guard was on the other side of the building so that when he came back, he couldn't see them sneaking inside. Unfortunately, the sudden lack of light alarmed him, which leads to another point:

The Chase Sequence

The way you describe the ninja character as cycling through backstab -> run -> hide -> backstab definitely confirms this as a bad pattern of stealth. One of the biggest flaws of the first Assassin's Creed game was how you could stab someone, run like heck, hide on a bench right around the corner, then go back and stab someone else. Rinse. Repeat. Worst of all, until they introduced notoriety in later games, it seemed like everyone forgot what you did.

Dishonored is a much better example of how to do detection and chase effectively. On the very first detection, the enemy is immediately alert and aware of the fact that you do not belong here. Hostility begins right away, and the chase is brutal. In a chase, NPCs do not let you get away unless you do something really daring. In the TV Show Burn Notice, the main character remarks during a narrative in a chase sequence that the only way to escape a chase is to do something that the people chasing you won't do -- like jumping off a roof.

And even if you get away, the NPCs should not just "forget" about you. They should be on high alert until you die or they are convinced that you have been driven off. Enemies on high alert for a stealth PC should not be easy to catch off-guard. In addition, they should not be splitting up alone if they are even reasonably intelligent.

Have NPCs adopt tactics like the PCs tend to act when encountering stealthy foes.

All Alone

"But I'm the only stealth character on the team!"

This is roughly the ninja player's position, I take it. I've been there. Fortunately, you don't have to be reliant on stab-and-run to be useful. A number of the former tips are intended for stealth-based encounters, but here's what a stealth PC has gotta do to have fun with stealth while your allies are kickin' down doors in the name of Tempus:

1: Wait for the encounter to get started. Be out of sight on the periphery. 2: Sneak up to a squishy target. 3: Stab. 4: ??? 5: Profit.

An ultra-stealthy character is ideal for taking out priority targets. Then, using other skills, such as acrobatic-type skills, make a daring escape. Not just running away by pure movement points, but dodging between pillars, leaping onto ledges, or tumbling past enemies to rejoin your allies.

Stealth should get you into the fray. Speed and tricks should get you out.

First, this adds variety to your actions as a stealthy character. Second, it should be hard to lose detection when enemies are tracking your movements so closely.

Beyond combat, a stealthy character can still be a great asset. Perhaps you can open a gate while the party is fighting. Maybe you can sneak into a camp and rescue a prisoner while the party is attacking from the opposite side. Generally, you should avoid going too lone wolf unless your party wants you to do so, because that's dangerous and slows down the game for others. Performing a stealth mission while the party fights a battle has been the best possible scenario in campaigns I have played. It keeps everyone busy, provides a distraction, and lets your group benefit from stealth simultaneously.

TL;DR version: Stealth should be more than dice rolls. It needs to interact with the environment and the intelligence of the NPCs involved. It should be rewarding, fast-paced, and require cleverness more than just sneakiness. When done right, it should give the party big advantages as a whole.

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    \$\begingroup\$ You haven't addressed any of the actual stealth rules of 5e in writing your answer and how the Author can actually work within the system. \$\endgroup\$ Jul 19, 2014 at 22:25
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    \$\begingroup\$ I think most of the answer is system independent \$\endgroup\$
    – Adeptus
    Jul 20, 2014 at 12:02
  • \$\begingroup\$ Yeah, my experience with 5e is too limited still, but I can gibe plenty of solid system-agnostic tips which will also work in 5e. \$\endgroup\$
    – Tanthos
    Jul 20, 2014 at 16:23
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    \$\begingroup\$ Although I like the answer by GMNoob, and it covers specific key points of the OP, this answer is an extremely well crafted one, and I feel it should be labeled as THE answer. A bit of editing to add rules specific comments and there would be little recourse but to label it as such. \$\endgroup\$
    – Aviose
    Jul 21, 2014 at 21:08
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There seem to be a few misconceptions going around the table.

Misconception 1. My players are not very tactical and like to run directly into encounters

Explain to your players that if they wish to be sneaky ninjas, they need to act like sneaky ninjas. If the rest of the team rushes into battle, the Ninja should be staying back and hiding out, making sure the coast is clear before revealing themselves. The Ninja should also be advising the rest of the team on tactics which can be used to grant a surprise round advantage, or ambushes, or how to avoid being surprised.

Misconception 2. "a character (at least I understand it that way) can't just roll Stealth and pretend to disappear to then use a Stealth Attack since enemies are aware of player positions most of the time."

While it is true, that enemies are aware of their surrounding during combat, because they are wary, it is not true that they always know where somebody is. If somebody has cover, and is not making loud noises, they can hide. No, you can't 'pretend' to disappear, but you can actually hide and not be seen. There are multiple narrative ways to do this. One example, as given in the Basic Rules, is that there are a pile of rags in the corner of the room, a halfling might be able to bury themselves under those rags, while nobody is looking. Another example is hiding behind a wall, or a wood Elf can blend in with fog or leaves, or rain. Anything that can cause another creature to not know where you are can allow you to hide. Stealth is really useful, and you might think that every character should use stealth. That might be true, but then as you say in your question, it's a waste of a move when you can just attack instead. This is why cunning action has limited usage to Hide, Dash, or Disengage.

Misconception 3: " I am constantly discussing with the Ninja that he's just wasting turn on hiding when he can flank with an ally to gain the sneak attack bonus."

Hiding, is not just good for the sneak attack bonus. Being hidden also causes disadvantage when enemies try to attack you (If you are behind cover this can almost be an effective +8 to AC!) Attacking from a place where you are hidden also gives you advantage. (Often an effective +4 to hit) If a player wants to be the type of character that is hidden, can't be hit, and has precision strikes from hiding spots, this is a very effective technique. He isn't wasting time, especially if he is a level 2 Rogue or higher. Cunning action allows them to hide, attack and move, every turn. Sneak Attack Damage is another extra nice bonus. And just to make it clear, the Ninja should be staying as mechanically close to the rogue template as possible, making sure that being a Ninja isn't worse off than a basic rogue and only the subclass features gained by Thief are being replaced.

Any ideas on how I can balance action and stealth without consuming too many rounds on doing so? That is what kills the fun for me - the character runs away, make stealth rolls, remain hidden, and suddenly attacks when he could gain the same bonus in one round.

There are a few things you can do

  1. Make sure they have the "Cunning Action" and know how to use it. (i.e.) Allow them to hide almost every turn.
  2. Create environment where it is easy to hide. Large stacks of crates, Guard boxes, Trees, Stuff with nets over them. For people who like to do stealth, stealth is a lot of fun, let them play it up.
  3. Don't worry that being hidden and Sneak Attack Damage, and rogues/Ninjas are too powerful. Even with all the great advantages of being hidden, and attacking from a hidden location, rogues still do not do as much damage per day as Clerics, Wizards, or Fighters. At low levels they will seem really powerful "because they are doing so much" but the reality is that they are doing "just the right amount". Sneak attack damage, and the increased effective AC from being hidden is what keeps Rogues on par with the other classes, it does not make them become better.
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  • \$\begingroup\$ I'd further emphasize that the Ninja should mechanically be as closely modeled on the Rogue as possible \$\endgroup\$ Jul 19, 2014 at 22:27
  • \$\begingroup\$ Recommendation #2 is the most essential. We choose to play as roguish characters because we expect that our enemies will have subtle weaknesses and plenty of blind spots, and we want to have fun exploiting that fact. Give your rogue lots of things to exploit. If he is not exploiting things, then he is not being a rogue. \$\endgroup\$
    – Jordan
    Jul 10, 2015 at 6:40
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If waiting a round kills your fun, you need to learn a little more patience.

Sure, the GM should have fun too. But if the rest of the group is supportive, and the player needs an extra round or two here or there to have fun with their character - man up and do it.

That's really the bottom line, though I would go on to say that limiting Stealth to "a chance to get a sneak attack in combat" is a pretty sad state of affairs, and that perhaps your players are getting rightfully sick of every game being an endless litany of "charge heedless into combat." That's usually fun at first, but once people have been gaming a while they often start looking for a little more sophistication in their fictional world.

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Quite simply, you need to give your stealthy character things to do that aren't simply "sneak on ahead of the party and backstab someone to open the combat round."

Basically, you need to offer bonus goals for the ninja to accomplish that piggyback on top of the rest of the team's tendency to stomp their way through encounters.

Do you have a big fight coming up? Perhaps the fight would be easier if someone were to tip the scales in the party's advantage before swords are drawn. For example, say you and your group is going to meet an army on the field of battle at dawn. They have ballistas and you don't. Send the ninja on ahead to sabotage the enemy artillery so that when dawn arrives, the party can meet the opponents as equals and not have to worry about having death rained down on their heads as they advance. How do you know the enemy has ballista? The ninja scouts the camp ahead of time and brings back that information. Did the party not give the ninja enough time to scout the camp? Oh well, after they barely survive an encounter against a heavily-armed enemy they may listen the next time when he says "Hey guys, I could have done something about that."

Even better, forget the ballistas and just assassinate the enemy leader. Best case scenario, the enemy doesn't go into battle without their commander. Worst case, they give a field promotion to the poor sap beneath him and wind up hampered by the leadership of a guy who isn't as experienced.

Whenever you design an encounter, ask yourself; is there a way to make this encounter easier? What can I add for the stealth character to do that would give the party an advantage? Then add that thing. If the group/player thinks to leverage it, great; they reap the benefits. If they don't, then they may still win, but without the edge that comes from playing smart. That leaves it in their hands.

Another example from my old Star Wars campaign, ripped shamelessly from the Phantom Menace; the party managed to get on board a Trade Federation starship and were confronted by the Big Bad Evil Jedi backed by a contingent of battle droids. The tech specialist had slipped away and found the droids' control beacon and hacked it, shutting them down. The rest of the party engaged the Jedi on more even footing. Could they have won the battle anyway? Probably, but it would have been harder. Could the party have just stormed the control center? Also probably, but confronting the Jedi and his entourage drew forces away from the control center, making it easier for the tech guy to sneak in. It would have been far riskier for him to try and shut down the beacon in a firefight, but it might have worked anyway. (See also: Guardians of the Galaxy,escape from the Kyln.)

Which leads me to my second thought; you can also create two-pronged encounters where the stealth guy has to accomplish his thing to get the rest of the group to their goal. Again, referencing Star Wars, the small strike team tried to sneak into the bunker on Endor and disable the shields so the fleet could destroy the Death Star. The Gungans met the Trade Federation on the plains of Naboo while the pilot-types attacked the control ship and a small team snuck into the palace. (The ending of TPM is actually a textbook example of how to leverage the skills of all players so that they have an effect on the plot; the Jedi got to be awesome sword fighting, the pilots got to be awesome dogfighting, and the warriors got to be awesome fighting on the ground. And then there's Jar Jar.)

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Make sure you understand the rules for stealth -- for example see How does Stealth work with Sneak Attack? . In particular, just because the enemy "knows where you are" does not prevent your ninja from stealthing. If I'm reading the rules correctly, the ninja could hide behind some other character and then pop out and make a sneak attack. (Because you can stealth "when you have cover".)

Beyond that, my recommendation is: stop saying no. Let him hide whenever he wants to hide, however he wants to hide. Let him hide behind other characters. Let him hide by making a Bluff check and saying "look behind you!". Let him hide behind objects that are much smaller than he is, because he's just that good at hiding. Let him improvise hiding spots -- if he says "there's a tree on the map right here, right, that I can hide behind?", tell him of course there's a tree right there, and you just forgot to put it on the map initially. His character will still be dealing less damage than the other characters, so you won't get balance issues for it. And he'll be having more fun, and that's what counts.

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    \$\begingroup\$ PS. You wrote: "I am constantly discussing with the Ninja that he's just wasting turn on hiding when he can flank with an ally to gain the sneak attack bonus." Probably the reason he's doing this is his AC and HP are too low to take attacks. He's worried that, if he flanks, the monsters will turn around and kill him. \$\endgroup\$
    – Dan B
    Feb 12, 2015 at 23:26
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The rogue is not just a product of fantasy mythology. It is not defined by its thematic flavor of skulking through the darkness, sneaking up on enemies and surprising them, stealing treasure (or keys) from under people's noses, etc. Nor is it defined by the D&D 5e rules of sneak attacks, hiding, lockpicking, etc. It is much broader than that. It is rooted in human psychology.

A rogue is someone who bypasses threats instead of facing them. Someone who avoids a fight at all costs, and when forced to fight, avoids a fair fight at all costs, preferring to get the upper hand with resourceful, dirty tricks. Someone who thinks "heroism" is silly and uses pragmatic methods instead of heroic acts. Someone who wears cowardice as a badge of honor. (I say this as a self-professed coward.)

To reward roguish players, give their enemies a death star with a small but fatal weakness. At the very least, this can be a fort with a well-guarded front gate and a largely ignored "secret" backdoor. First, introduce the death star. Show how formidable it is. Let them attack it head-on and see for themselves that they stand no chance against the overpowered enemies defending it. Let them despair for a bit. Then put some information into the game that hints at the "secret" weakness. Let the rogue scout it out and find that it is sorely underprotected, if at all protected. And finally, when the party accomplishes its goal (maybe by assassinating someone, or by retrieving intel), reward the party with significantly more wealth and experience (and better long-term consequences for the plot) than they would have gotten from a head-on assault, and make sure they know that the reward for bypassing the threat is greater than the reward for facing it would have been.

If you are strictly looking for ways to make stealth-based combat more enjoyable, then you have doomed your efforts from the start, because the way to make stealth more enjoyable is to make combat avoidable in the first place.

But even in combat, stealth can be more or less enjoyable. It depends on how exploitable the combat space is. Minimize the amount of open-field combat in broad daylight, where there are no features to exploit. Whenever designing a dungeon or room or other piece of space, think about what the blind spots are, and from which angles. Play around with patches of darkness, lights that can be put out, objects that can be improvised as arrow slits, etc.

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Ask him what character he wants to play.

Would he like flit around in the middle of combat but is scared to because he's too squishy? Does he WANT to be a "hide in the shadows and snipe enemies" character, but isn't getting mechanical rewards for that? Would he like to have more infiltration outside combat, but the group is fairly combat focussed so it's hard to squeeze in?

Make what he's doing now more effective

This may be easy. If he wants to be in the thick of it, allow him to redesign his character and offer some advice (from yourself or another experienced player) how to do so effectively.

If he wants to be "lurk in the shadows during combat" ninja, try to tune things so that works. Encourage him towards ranged attacks? Or homebrew a version of the rogue combat so he's rewarded for the sort of things he wants to do. Houserule a version of sneak attack that doesn't reward an enemy being adjacent, but gives bigger damage if he's attacking from hiding. Houserule a lower-level version of a death-attack where if you "study" a target for several turns, you do a big damage attack.

Add more stealth options

Have the combat about something, not just "defeat the enemy". If it's "rescue the prince" or "capture the druid" or "defend the drawbridge", there may be sensible tactics for "you four, charge, you in the black cloak, sneak round in the distraction and try to get the prince untied". That allows him to have actions at the same time as other people are having combat.

Have situations where scouting before combat is obviously sensible -- the enemy slumbers in their cliff-side hideout, can someone scale the cliff and throw down the rope ladder without alerting the enemy?

Even if combat is generally "charge towards each other", have some monsters who hang back, eg. "the wizard sends the orcs charging into combat, but ducks into the high pulpit, sniping powerful spells", obviously balanced so it's fair-ish. Aim for a situation where even straightforward players will get the idea that ignoring the wizard is too dangerous, and fighting to him is difficult, but he's not that armoured and one sneaky-dude could likely take him out or at least distract him.

Check the existing rules

Is he aware that the rogue can sneak-attack with a ranged attack, provided his ally is adjacent to the target? Like flanking in previous editions. This seems to give a "attack from the shadows" option. Does he understand the options available from the rogue's bonus action (hide/disengage)? It sounds like you've already talked about this but I wanted to make sure.

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