DnD 5e - Rogue Subclass Breakdown
Last Updated: July 10th, 2021
Rogue subclasses are extremely powerful, frequently granting features at 3rd level which define how your character plays for the rest of their career, and offering a tempting prize for builds which can handle a 3-level class dip.
RPGBOT uses the color coding scheme which has become common among Pathfinder build handbooks, which is simple to understand and easy to read at a glance.
- : Bad, useless options, or options which are extremely situational.
- : OK options, or useful options that only apply in rare circumstances.
- : Good options.
- : Fantastic options, often essential to the function of your character.
I will not include 3rd-party content, including content from DMs Guild, even if it is my own, because I can't assume that your game will allow 3rd-party content or homebrew. I also won't cover Unearthed Arcana content because it's not finalized, and I can't guarantee that it will be available to you in your games.
The advice offered below is based on the current State of the Character Optimization Meta as of when the article was last updated. Keep in mind that the state of the meta periodically changes as new source materials are released and this article will be updating accordingly as time allows.
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The Arcane Trickster brings magic to the Rogue. Enchantment and Illusion spells both offer fantastic options, giving the Arcane Trickster powerful options utility and trickery, but also bringing powerful offensive magic options.
Because it's the only rogue subclass with a spell list (or with any decision points made after level 3), the Arcane Trickster is the most complex rogue subclass to build and in many ways it's also the most complex to play because you have so many options to consider in any given situation. I don't recommend the Arcane Trickster for new players, but managing the Arcane Trickster's spellcasting is not nearly as complex as that of a full spellcaster like the Sorcerer or the Wizard, so an arcane trickster may be a good stepping stone if you're nervous about playing a spellcaster.
Because your choice of spells is so central to the Arcane Trickster, I strongly encourage you to read my Rogue Spell List Breakdown.
For help selecting spells, see my Rogue Spell List Breakdown. : The Arcane Tricksters defining feature. You're limited almost exclusively to Enchantment and Illusion spells for your leveled spells, but both of those schools work very well for Arcane Tricksters. When selecting spells, remember that Sneak Attack requires Dexterity-based weapon attacks, so you can't apply it to spell attacks. Instead, you'll generally rely on spells like Booming Blade and Shadow Blade.
- : Controlling the hand as a bonus action means that you can pick locks and pick pockets while you're doing other things fighting or casting other spells, and since the hand is invisible you can send it off to do those things unnoticed while you and your allies are busy hiding, fighting, carousing, or whatever else you do with your day.
- : Since your spell DC likely won't be as good as that of a dedicated spellcaster this can really do a lot to improve the reliability of your spells. I'm still nervous to recommend spells which require saving throws as a go-to optionfor the Arcane Trickster, but mathematically it makes sense. Disadvantage works out to slightly more than a -3 penalty, so if your Intelligence is 14 or higher your spells can be roughly as reliable as those of a wizard with 20 Intelligence.
This feels redundant with the Steady Aim class feature, and since most rogues won't make more than one attack per turn, in a practical sense they have the same effect. You cold use this with spell attacks like Scorching Ras, but hitting with Sneak Attack is less expensive and deals comparable damage so that's generally a bad combination. You're much more likely to use your hand to get Advantage before attacking when you can't be invisible for whatever reason. : Advantage allows you to Sneak Attack the target. Remember that you will need to move the hand into range for this to work, but you can use your Cunning Action on the previous round to do so thanks to Legerdemain and since your Mage hand is invisible enemies won't know that you're doing so.
- : The obvious use it to steal spells from enemy spellcasters, but in a game when you might go several levels without seeing a spellcaster, a better option is to "steal" spells from your party's other spellcasters. Have them cast a useful low-level spell on you, like a buff spell or Polymorph, and cast it on your own without needing to consume other spellcasters precious spell slots.
Assassins are good at two things: Infiltration and (you guessed it) assassination. If you want to get into places unsuspected or just straight up murder people, the Assassin is the way to go. However, they lack utility options for handling situations outside their specialized skillset.
Assassins have a weird divergence in their subclass features where Assasinate and Death Strike emphasize frequent combat, while Infiltration Expertise and Imposter both work in campaigns where you're doing a lot of spying, infiltration, and intrigue. This doesn't stop them from being excellent in your typical dungeon crawl, but if you're going from levels 1 to 20 in a full campaign you may rarely see some features come into play.
Because their premise and their features are so simple, the Assassin is one of the easiest rogue subclasses to play. They don't have resources to track or complicated additional mechanics, so if you're comfortable with the complexity of the Rogue's core features you're already ready to handle the Assassin.
- : Both tool kits are fantastic and open up wonderful options for the Rogue.
Critical hits are very powerful for rogues because critical hits multiply your Sneak Attack damage. Imagine how satisfying it is to roll that big pile of d6's, then consider how good it will feel to roll it twice. Your weapon's damage is also multiplied as normal, but your damage die will be a tiny portion of your overall damage so don't stress too much about trying to find a big damage die. : To make this work, you really want to go first in combat. Maximize your Dexterity as soon as possible, and consider the Alert feat. If magic items are available to you, try to get a Weapon of Warning.
- : Situational, but very flavorful, and absolutely fantastic in some situations. If you're getting a reputation for being an assassin, maybe it's time to take on a new identity. Start fresh. Introduce yourself to your party as a completely different assassin that's definitely not the same person who has been in the party since level 1. Or maybe the party knows what's up and they just need to start calling you by a new name or something.
- : Very rarely useful in most campaigns, but very flavorful and usually hard to accomplish without magic.
- : Combined with Sneak Attack and Assassinate, this is an absolutely huge pile of damage.
If you want to be really good at Insight and Perception, this is the way to do it. Combined with Expertise there's no one who could reasonably compete with the Inquisitive's powers of perception.
However, the archetype offers very little to do once you notice stuff. It would be great in a campaign that includes lots of traps, hidden doors, and people who lie to you, but in situations not specifically tailored to the Inquisitive's skillset they fall back on basic Rogue class features. In combat, the Inquisitive's only new features are Insightful Fighting and Eye for Weakness. Insightful Fighting can be replaced by having one ally who's fighting in melee, and Eye for Weakness is weak compared to other subclass features at the same level.
The Inquisitive is a cool concept, but it needs something active to do once it spots things beyond Sneak Attack. As a fix: Allow the Inquisitve to ignore Disadvantage when attacking invisible foes which you have targeted with Eye for Detail, and add the Rogue's Wisdom bonus (or Proficiency bonus, but that might be too much) as a damage bonus against targets affected by Insightful Fighting.
- : This only applies to Wisdom (Insight) check to determine if a creature is lying, and while it's nice to have that level of insurance, it's still only situationally useful and it's easy to misread this and assume that it applies to Eye for Detail and Insightful Fighting.
- : Finding hidden creatures normally requires an Action to attempt, which is a serious problem if you're ever attacked by stealthy enemies which like to hide and snipe at you from afar. Of course, in a typical party you can handle invisible enemies with magical options like Faerie Fire or Glitterdust.
The effect lasts for a full minute so you have plenty of time to benefit without repeatedly spending your Bonus Action on the same target. Even if you lose the opposed check, you can try again the following round, and the every round after that until you succeed. Of course, if you have another ally fighting your target in melee, this gets you absolutely nothing.
Compare this to the Steady Aim Optional Class Feature: Steady Aim is a Bonus Action, doesn't require a check that you might fail, and grants Advantage on your attack rather than simply enabling you to use Sneak Attack. Steady Aim lasts for a full minute, but only if you don't change targets. : I hope you took Expertise with Insight, because it's your signature feature and if you can't reliably pass this check you're basically back to core rogue features in combat.
- : Combined with Eye for Detail you're extremely reliable at spotting traps and hidden enemies, but the limitation on movement might be a problem in combat, especially if you're built for melee. If the movement issue isn't a problem, this makes Insightful Fighting much more reliable.
- : Wisdom isn't an especially useful ability score for most rogues beyond skills, so it's frustrating that this ability is Wisdom-based. The effect is extremely useful, but you'll likely get no more than two or three uses per day, and you need to either already know that illusions are present or you need to guess.
- : Extra damage never hurts, but it's not very exciting and compared to other subclasses this is a pittance. Compare this to the Thief's Thief's Reflexes feature or the Assassin's Death Strike feature. In a long fight, additional Sneak Attack damage may eventually outshine other options, but a typical fight lasts just 3 to 4 rounds, and you need to climb the mountain of additional damage that's being dealt by the Arcane Trickster with bonus damage from spells like Shadow Blade, the Assassin with Assasinate, and the Thief with a second turn from Thief's Reflexes.
Okay, but what if Ouija boards were a subclass? What if, like, you got class features from talking to dead people? And what if those class features included necrotic damage and turning into a ghost? Enter the Phantom.
The Phantom is a novel exploration of interactions with the dead as a class feature, making necrotic damage and death-related stuff available to a class with no ability to cast spells. Normally, interacting with the dead is primarily done by clerics and certain necromancy spells. The Phantom has a much more direct connection to the spirits of the dead, gaining proficiencies, damage output, and the ability to turn (mostly) into a ghost.
The Phantom's most novel and interesting mechanic is their pool of Soul Trinkets. These trinkets allow the Phantom to fuel their most interesting features by gathering trinkets when creatures die nearby, then spend those trinkets for extra damage or to ask dead creatures questions. Tragically, this feature doesn't become available until 9th level. Waiting for creatures to die rather than being reduced to 0 hit points also makes it important for the DM to track death saves for enemy creatures, which is a minor annoyance that most DMs are happy to avoid, so discuss how your DM would prefer to handle that aspect of the subclass.
Players may also find that Wails from the Grave is underwhelming at low levels compared to other subclass features at the same level. Phantom definitely builds slowly, and may not feel really satisfying until level 9. As a quick fix, give players the Soul Trinket mechanic at level 3 instead of level 9, but don't grant them Advantage on Constitution saves or the ability to spend Soul Trinkets to ask dead creatures questions until they reach level 9. Essentially, you're splitting the Tokens of the Departed feature into two. At low levels, the player's low Proficiency Bonus will keep Wails from the Grave from getting out of hand, and even if they're spamming it constantly the damage is minor so it's not going to result in a massive boost in damage output. This change will make the subclass more satisfying to play and will give access to the subclass's signature features earlier without significantly changing the balance of the subclass.
Most of the time you can leave this on a low-importance skill proficiency, but most tools won't come up unless you've got time for a short rest. No one is going to ambush you and ask you to break out the Brewer's Tools and make them some beer (I've made beer. It takes a few hours, and spending one hour to take a nap first isn't a big ask. I've done that, too.). : The ability to pick up a proficiency on short notice is incredibly useful. If you can combine this with other buffs like Enhance Ability and Guidance, you can get around nearly any skill-based or tool-based challenge if you have time to prepare.
- : Starts very slow (1d6 twice a day), but ramps up exponentially as your Sneak Attack damage and your Proficiency Bonus increase. The damage is necrotic, which is rarely resisted, and it's automatic provided that you made a successful Sneak Attack so it's great for enemies that may be difficult to hit. Even as it gains in power, you don't want to throw this around needlessly. You'll never get more than 6 uses (not counting Tokens of the Departed) and they'll never deal more than 5d6 damage, so you need to be strategic.
The first benefit is without doubt the best of the three, and it's good enough that you should nearly always keep a Soul Trinket handy. Advantage on Constitution saves isn't quite as good as proficiency, but it's close. Unfortunately, the Phantom doesn't need to worry about Concentration unless you take Magic Initiate or Multiclass, so you don't get to wave your token around every time you cast a Concentration spell.
The second benefit helps with Wails of the Grave, and it's easily your most frequent way to spend trinkets. Wails from the Grave is a decent bit of damage by this level, matching what a spellcaster can do with many cantrips. However, the Proficiency Bonus usage limit won't get you far, so you can destroy a trinket to get a free bit of damage. Every time you think "is a new trinket worth my Reaction right now?", remember that it's a small pile of easy necrotic damage when you need it later.
The third benefit is basically Speak with Dead, but you only get one question. Otherwise, it has all the same problems where the subject can be vague, misleading, or otherwise unhelpful. Very situational, but if you can somehow make it work it's excellent. This also has a curious edge case where the creature which allowed you to produce the token might be alive again, especially in cases where your allies die and a raised from the dead. You might use this to ask a question of a creature who is currently alive, leading to hilarious situations where the ghostly apparition of a living creature appears in the same room as that creature only to say something totally unhelpful before disappearing.
The one flaw in the whole thing is that it falls prey to the classic "Bag of Rats" trick. You can kill any creature to generate a new Soul Trinket, so if you have a bag of rats or access to other easily-expendable creatures, you can kill them out of combat to recharge. Your DM might justifiably make some adjustments to disallow that (requiring a CR above 0 may be sufficient, especially at 9th level), so try not to lean on the abuse case too much. This generally won't work with summoned creatures (they need to die, not just be reduced to 0 hit points), and since death and being reduced to 0 hp suddenly mean different things, I encourage DMs to start tracking death saves for enemies. : I love everything about this feature. The theme is cool, the mechanic is fun, the resource pool is appropriately limited but easy to restore, and the benefits are fun, thematically appropriate, and really good. You get three benefits at level 9, but at level 13 you can recharge Ghost Walk with a trinket and at level 17 you wake up from longs rests with a free soul tinket.
- : A 1-minute duration on this would be good. A 10-minute duration on this is fantastic. 10 minutes is obviously plenty if you're using this in combat, but it's more important outside of combat where you might need to move through walls, floors, or ceilings while scouting. The 10 ft. move speed is tiny, but remember that you have Cunning Action so you can Dash as a Bonus Action. If you can get buffs like Longstrider, they'll do a lot to help both because any flat numeric increase is relatively large compared to 10 ft. and because you can essentially double the effect by dashing without spending your Action.
The second benefit of this feature ensures that you have at least one Soul Trinket at the end of a Long Rest. This is a crucial benefit so that you can benefit from Advantage on your Constitution saves, so try not to burn your trinket the first time you want to use Wail of Souls. But since you get the trinket for free, this also makes it easier to spend your last trinket right before you take a long rest. Of course, you could just use the bag of rats trick to get free Soul Trinkets, so this benefit isn't as impactful as WotC wanted it to be when they wrote it. : At this level Wails of the Grave deals 4d6 damage, just short of its maximum at 6d6. Adding that damage to your primary target when you use Wails of the Grave means that your Sneak Attack deals 50% more damage, though it's not clear if you can multiply the damage on a critical hit. I believe that you can't because the damage is applied to the target from a separate source rather than added to the damage of original attack like effects like Divine Smite.
The Mastermind works best in a game with a lot of intrigue and social interactions. The only feature which applies in combat situations or in a dungeon crawl or something is Master of Tactics; everything else is for social situations. You can scrape by on core rogue class features, but outside of a highly social campaign, the Mastermind is going to struggle compared to other rogues. Even in campaigns where the Mastermind is well-suited, you will need to work to make your features meaningful and your DM will need to tailor the game to your capabilities.
- : A pile of proficencies which you might never use, but in an intrigue game this offers some very exciting tools.
- : Help gives the target Advantage, which is pretty great for a lot of characters. Of course, as a Rogue no one needs Advantage as much as you. Using this as a bonus action prevents you from using Cunning Action or two-weapon fighting, so your Bonus Actions will always be a very difficult trade-off. A good use case would be to use Master of Tactics to give your party's Fighter-equivalent Advantage, then ask them to Shove a target prone so that you can get Advantage on subsequent turns.
- : A fun way to metagame, but not always useful since in most games you typically won't get to spend a minute chatting up enemies before weapons come out. In intrigue games this could be a neat way to learn about a creature, but you don't get a clear mechanical way to make this information useful, so it's often little more than trivia and a hint at how the creature is built.
I think the intent is to use enemy creatures as cover while you're being attacked at range, but that situation is uncommon, and enemies will typically choose to shoot one of your other allies instead rather than try to overcome your high AC thanks to cover. : Lightfoot Halflings have the ability to hide behind creatures one size larger than they are, which will often also give you cover. It can be a bit rude to shuffle attacks onto an ally, but if you're using a well-armored ally as cover, sometimes your ally may be better suited to absorb the attack, and your party's Defender generally goes into combat explicitly hoping that they'll draw attacks away from you and your other squishy allies.
- : Very situational. Characters in a typical campaign might be subject to such effects once or twice if they run a full campaign from levels 1 to 20, and even in a intrigue campaign where you might face other sneaky people with options like telepathy or spells like Zone of Truth, those options are typically limited to powerful characters and won't be applied to you so frequently that this is justifiably as a level 17 feature.
Scouts easily outcompete Rangers in skill use with Nature and Survival, but lack any of the actual Ranger flavor. If you want to play a Rogue in a wilderness game, you could definitely do worse, and it's hard to think of a better way to make a Rogue that uses a bow. The Scout manages to keep you at a nice safe distance, keeping you safely out of attack range while your allies distract enemies long enough for you to Sneak Attack them.
You can't use this until an enemy ends their turn, so they've already done any attacking which they plan to do, and you may have used your Reaction on Uncanny Dodge to mitigate damage from a hit. If you're built for melee, using this often means spending more movement on your turn to get back into melee, so reserving your Reaction for Uncanny Dodge is a better investment. If you're built to fight at range, you can use this to get out of almost any creature's reach, then you'll still have your movement and your Bonus Action on your turn to use Cunning Action for something else more exciting than Disengage. : Spectacular for ranged builds, but less helpful for most melee builds, and since it works as a Reaction it can conflict with Uncanny Dodge. Cunning Action can also solve the same problem, so Skirmisher feels like a miniscule addition your capabilities.
- : Two new skills and Expertise in both of them, giving you Expertise in a total of four things (provided that you're not also getting Expertise from other places). Both skills are Wisdom-based, and Survival isn't especially important, but Expertise will easily make up for a relatively poor Wisdom score compared to a druid or a ranger.
- : Really helpful in conjunction with Skirmisher and your need to stay as far away as you can.
- : Consider the Alert feat for the bonus to Initiative rolls. You want to go first to maximize the utility of this feature. Encourage your allies to focus on your target and quickly eliminate high-priority targets early in the fight before worrying about other enemies.
- : This extra attack consumes your bonus action, so two-weapon fighting is redundant. Allowing you to Sneak Attack twice in a turn effectively doubles your damage output, which is amazing at any level. Unfortunately, you can't Sneak Attack the same target twice in the same turn with Sudden Strike, so this is considerably easier to use with a ranged weapon.
The Soul Knife is a psionics-based option for the rogue. Your subclass features are fueled from a pool of Psionic Energy dice which work in many way like the Battle Master Fighter's pool of Superiority Dice (spend a die to do a thing, and you typically roll the die and add it to the effect in some way).
The most notable aspect of the Soul Knife is how safe it is to use Psionic Energy Dice. Rolling dice to use your subclass features is almost never a gamble for the Soul Knife, and few other classes/subclasses with similar resources can say that. Battle Masters gamble their Superiority Dice. Bards gamble their Bardi Inspiration. Even the Psi Warrior gambles their Psionic Energy Dice to some degree.
With some exceptions, the Soul Knife always get something for their Psionic Energy Dice, and if you fail on whatever roll you often get to keep the die you used. That makes it easy to stretch your limited resources through the day, and it's an incredible comfort for players who have consistently poor rolls (or who feel like they do).
The Soul Knife's reliable resource pool makes them a comforting option for players who might have trouble weighing risk/reward calculations at the table when handling things like spell slots. But even if you're fine with those decision points, it's an all-around reliable and effective subclass with a lot of offer.
If your DM adheres to the Adventuring Day rules, that means you can recharge as many as three dice per day. Across a full day of adventuring that's a small pool to work with and you need to be cautious about spending your dice rather than burning through them in the first encounter. The Soul Knife's Psionic Energy Dice are much easier to retain than the Psi Warrior's because they often aren't expended if you fail a roll, but even so at low levels you'll need to be prudent about when something is worth a die.
: Your pool of Psionic Energy Dice are your defining resource. You get a number equal to double your Proficiency Bonus and the size goes from d6 to d12 over the course of your career. That sounds like a big pool, but they mostly recharge on a Long Rest, and between long rests you can recharge just one die as a Bonus Action once per Short Rest.
- : Even though this only works with skills and tools, it's still really good. If you fail the check you can roll a die even if the chances are incredibly slim that it will make a difference, and if you still fail it costs you nothing. Every other ability like this requires you to gamble the resource on the possibility of success.
Don't forget: you get this once per day for free, so there's little reason to avoid using it. : Rary's Telepathic Bond is a 5th-level spell, and you're replicating its effects (mostly) at level 3. Rary's Telepathic Bond also notably has a 1-hour duration, and you get 1d6 hours (up to 1d12 hours at 17th level). You're limited to adding 2 allies when you get this (you're in the group for free), but the number increases with your Proficiency Bonus.
The ability to make a second attack as a Bonus Action if you have another free hand is great. Two-weapon fighting is already a great fallback option and since you don't need to draw daggers to repeatedly throw them you don't need to strain your Free Item Interaction every turn to keep your hands full of pointy things. But the benefits go further. The second attack applies your Ability Modifier to damage since you're not actually using the two-weapon fighting rules. Sure, the second blade uses a slightly smaller damage die, but who cares? That's such a tiny, meaningless difference that I'm surprised they bothered to print it.
However, this feature does have some drawbacks. You'll be unarmed after attacking with both blades, which means that you can't use Opportunity Attacks to get extra Sneak Attack on other people's turns (unarmed strikes are still possible, but don't qualify for Sneak Attack). You can mitigate this somewhat by drawing and stowing a dagger before or after attacking on alternate turns, but that trades your Free Item Interaction every turn for the ability to make meaningful Opportunity Attacks every other turn. That's a hard trade, not to mention how annoying it is. You could also get Fighting Style (Thrown Weapon) which will allow you to draw a dagger as part of the making the Opportunity Attack, but that may not be worth the cost to do so.
Also, since your Psychic Blades can only deal psychic damage, if you run into something immune to it you lose half the functions of your subclass. You'll need to carry a dagger (ideally a magic one) as a backup. : This is your primary combat option. You can attack with the blades equally well in melee and at range, and with a range of 60 feet your range is much greater than that of a rogue using daggers. The fact that this deals psychic damage is great, too, since it's so rarely resisted and easily bypasses common resistances to non-magical weapon damage. Oh, and it's a d6 damage die instead of the dagger's d4.
: Two ways to turn your Psychic Energy Dice into solutions to frequent problems.
- : Use this on the last attack of your turn (maybe you don't want to attack with both of your Psychic Blades every turn; Cunning Action also exists), provided that you can deal Sneak Attack with that attack. If you miss the initial attack, you can try to turn a near miss into a hit. If you still miss, this costs you nothing. If you do hit, you're trading your Psionic Energy Die for a Sneak Attack. That's a very good trade.
- : Even moving the minimum of 10 feet is enough to get you out of grapples and many area control effects, as well as through many tight openings like arrow slits. However, if you need to cross a large gap you'll find that the unpredictable range is frustrating. Fortunately, you choose whether or not you want to teleport after you roll the die so you never need to worry about accidently teleporting yourself above a pit of acid or something, but you're committing to spend the die before you roll it so look for other options if you're not likely to get as far as you need to go.
- : Invisibility for a full hour, and you get it once per day for free. An hour is a long time, and you can do a lot of things without breaking Invisibility, including things like disarming traps and taking the Help action to help allies in combat. You can spend a Psionic Energy Die to recharge it, but that's an easy way to spend your dice very quickly when mundane Stealth checks will often suffice.
- : Note quite as good as Hold Monster, but about as close as you can get without casting it. Stunned takes the target out of the fight and makes it very easy to kill them. Since the DC is Dexterity-based your DC will match that of spellcasters. You get this once per day for free, but it's probably worth spending three Psionic Energy Dice to recharge it if you find another target with poor Wisdom saves.
The Rogue's biggest challenge in combat is applying Sneak Attack reliably. While that's relatively easy in 5e, there are still times when you won't manage to Sneak Attack. The Swashbuckler all but eliminates these times, making the Rogue an even more reliable source of damage. In addition, the Swashbuckler has fantastic abilities for moving through combat, evading enemies, and even forcing them to engage the Swashbuckler, thereby allowing the Rogue to serve as the party's Defender on top of their typical roles as a Scount and Striker.
On top of their excellent combat abilities, the Swashbuckler encourages you to invest in Charisma and play a Face, allowing the Swashbuckler Rogue to thrive both in combat and in social situations. If you diversify your skill proficiencies, you can be just as effective in exploration scenarios as other rogues, but you may find that you're strained for skill proficiencies unless you get extra from your race or pick up a feat like Skill Expert. It's hard to be amazing at all three pillars of the game (exploration, social interaction, and combat), but the Swashbuckler manages it without relying on magic. Few characters can say that.
- : You only need to attack the target, not hit them, so if you miss and don't want to stay in melee range you're free to retreat unimpeded. Using two light-weapons for two-weapon fighting allows you to move past and attack two enemies if you feel the need. The choice between using Cunning Action to Disengage and relying on Fancy Footwork will depend both on what you're wielding and on how many enemies you need to evade.
As long as you can get away from other enemies (such as by using Cunning Action to Disengage) you're nearly guaranteed to be able to Sneak Attack. Since you still need to be within 5 feet you're likely making melee attacks, but you could technically use a crossbow with Crossbow Expert.
Oh, and as if this wasn't absurdly good already, you add your Charisma bonus to Initiative checks on top of your Dexterity. : This is absurdly good. Any Rogue can Sneak Attack if an ally is within 5 feet of the target. Rakish Audacity allows you to Sneak Attack if no one except the target is adjacent to you, which means that as long as you're not getting mobbed you can reliably Sneak Attack whenever you hit.
Tanking generally isn't in the Rogue's skillset, but the first portion of this feature is a taunt mechanic. The DM could technically end the ability by having the creature walk out of the 60 foot range before returning, but that would be a cheap metagame trick, so feel free to shame your DM if they try it. With passable AC and Uncanny Dodge, you can easily handle being one creature's sole focus for extended periods, leaving the rest of your party to handle the rest of the encounter until one section of the party comes to help the other.
Out of combat, you can use this to Charm creatures, making them a very loyal friend for a very brief period. The effect doesn't let the creature know it was charmed or that you did anything unusual, and since it doesn't grant temporary immunity or have a usage limitation, you can use Panache on the same creature repeatedly to keep it Charmed. If you can succeed on the initial Charisma (Persuasion) check, this will trivialize social interactions with single creatures that aren't already hostile to you. : Be sure to take Expertise in Persuasion to make this work. It's worth the investment.
- : Advantage is great, especially on a skill like Athletics which is used to Shove enemies prone. Unfortunately, this uses your Bonus Action just to grant you Advantage, so you still need to use your Action to use the skill, leaving you no opportunity to attack. You're most likely to use this to escape grapples, to leap over difficult terrain, or do other fancy stuff like that.
- : Sometimes you can't risk missing, and in those cases this is a life saver. Most of the time you can still use Fancy Footwork to move away and return to attack later, but sometimes that just isn't an option and you need to deal damage right away rather than letting things drag on.
The Thief is the iconic Rogue, but that is not to say that it's boring. A Thief is reliable and very effective at the tasks which you most associate with Rogues.
Most of the Thief's complexity is tied up in Fast Hands, and if you can't get a good understanding of Fast Hands you're going to struggle with the Thief. Be sure to read my Practical Guide to Fast Hands, then load of up on caltrops and flasks of oil and get ready to rock.
- Practical Guide to Fast Hands to get clarity on how this works. : Disarming traps and open locks can typically wait until you finish combat, but using an item as a Bonus Action can include cool things like caltrops, healer's kits, even attacks with certain items. This is the most complex part of the Thief, so I strongly recommend reading my
- : Very situational, and several years into 5e's life, this feels like a weird relic from much earlier in the games history. At this point, there are abundant options for climb speeds and magical flight, so this is only impactful when those options are unavailable to you. Still, adding up to 5 feet to your jump distance makes it easy to jump over difficult terrain and other obstacles.
- : If you combine this with Expertise, you are as close to undetectable as you can get without being magically silenced and invisible. But as nice as this is, you can replicate it with a Cloak of Elvenkind, which is an Uncommon magic item.
- : This opens up all manner of weapons, wands, and staves which are normally limited to specific characters. Go poke around in the magic item sections of my class handbooks and look for treasures to steal.
- : Two entire turns is crazy. You can Sneak Attack twice and use Fast Hands to throw two vials of alchemist's fire, possibly all before enemies get a chance to act if your initiative roll was really good.