D&D 5E A Knife in the Dark, A Rogues Handbook

[clutchbone]

"Rogues, would you live forever?"
- Frederick the Great


Contents:
1. Overview
2. Know Your Role
3. Ability Scores
4. Races
5. Backgrounds
6. Rogue Class Features

· Melee vs Ranged​

· Skills​

7. Roguish Archetypes

· Spells​

8. Multiclassing
9. Feats & Example Builds
10. Tips, Tricks & Handy Links

1. Overview
Ah, the lovable Rogue. The adventurer who lies, cheats, steals, stabs people in the kidneys, and really isn’t all that lovable now is he? Unless, of course, he’s on your side. After all, no one else is crazy enough to stick their fingers into that spring-loaded trap, or to sneak off alone and make a grab for that frost giant’s key ring. He’s a useful chap to have around and you’re pretty sure you believe him when he says that your kidneys, at least, are safe.

2. Know Your Role
Rogues in 5e can expect to dish out respectable amounts of single-target damage while also taking point on a variety of skill checks. Rogues are not front line warriors; they have neither the hp nor the AC for prolonged exchanges. Instead they dart in and out of melee, or fire arrows from afar, while using their dirty tricks to avoid, reduce or even negate damage that comes their way. Keep in mind that although a Rogue's damage output is not the highest in the game, their stronger out-of-combat presence and unique defensive features make up for it.

From this point forward, the following colour coding will be used:

Cyan = Very good
Blue = Good
Black = Average
Purple = Bad
Red = Very bad


3. Ability Scores
Pump Dexterity and do as you will with the rest. Certain class features (Expertise, Reliable Talent, Slippery Mind) can help compensate for low or mediocre scores for certain skills or saves. This guide assumes you're using the point-buy variant for character creation.

Strength: 1/1 related skills are available to Rogues. Viable dump stat. This is for Athletics checks only, and you can get by without it. Aspiring spider monkeys may want 10-14, others want 8-12. You could build a Str-based rogue, but you’ll need specific race, feat, and/or multiclassing choices to make it work, and note that Sneak Attack still needs a finesse or ranged weapon.

Dexterity: 3/3 related skills are available to Rogues. One of the big three saves. This is for attacks, damage, AC, Initiative, skills and class features. Everyone wants 16-17. Str-based rogues will still want 12-14 here.

Constitution: 0/0 skills. One of the big three saves. Hit points are important, but you will develop ways to avoid or mitigate damage. Melee rogues want 14-16, others want 12-14

Intelligence: 1/5 related skills are available to Rogues. Viable dump stat. Arcane Tricksters will want 16-17, others want 8-12.

Wisdom: 2/5 related skills are available to Rogues, including the all-important Perception skill. Viable dump stat. One of the big three saves. Scout-types want 14-16, others want 8-14.

Charisma: 4/4 related skills are available to Rogues. Viable dump stat if you aren’t a people person. Silver-tongued rogues and Swashbucklers want 14-16, others want 8-14.


4. Races
When choosing a race, you want a Dex boost first and foremost. Also, note that darkvision is more important for Rogues than other classes for two reasons. Firstly, darkness, as a "heavily obscured area”, confers the "blinded" condition which imposes disadvantage on attack rolls, and you aren't allowed to Sneak Attack when you have disadvantage. Sunlight sensitivity has the same issue (disadvantage on attack rolls in direct sunlight), but that’s only a problem for drow & duergar. Secondly, Uncanny Dodge only works against opponents you can see.
[sblock=Player’s Handbook, Common Races]Dwarf: All dwarves get +2 Con, darkvision, advantage on saves vs poison and resistance to poison damage, proficiency with some non-finesse weapons and artisans tools, and a bonus to Int(History) checks with stonework. These husky fellows are built to be front line meatshields, not sneaky skirmishers. 25ft speed limits Cunning Action's mobility.

• Hill Dwarf: +1 Wis and +1 hp per level.
• Mountain Dwarf: +2 Str and racial proficiency in medium armor. This is the only race so far that gets dual +2s. These guys are your best bet for a Str-based rogue.

Elf: All elves get +2 Dex, Darkvision, Trance, advantage vs Charm, immunity to magic sleep, and Perception proficiency. Trance lets you sneak about for 4 hours while everyone else is sleeping.

• High Elf: +1 Int, free wizard cantrip, an extra language, and longbows. These guys were made to be Arcane Tricksters, although they'd still excel in any archetype.
• Wood Elf: +1 Wis. Having +5 ft speed, longbow proficiency, and the ability to hide while only lightly obscured in a natural setting makes Wood Elves into excellent scouts and skirmishers.
• Dark Elf (Drow): +1 Cha. Although they have decent stats, doubled Darkvision range and some innate spells (faerie fire is awesome for Sneak Attacking), sunlight sensitivity is bad if you’re not in dense forests, dungeons, inside buildings, etc.

Halfling: +2 Dex, Lucky, Brave, Halfling Nimbleness; all great for rogues. Unfortunately, 25ft speed limits Cunning Action's mobility and they don't have darkvision.

• Lightfoot Halfling: +1 Cha. Naturally Stealthy (use Cunning Action to hide behind an ally and immediately shoot off a Sneak Attack), is probably the single best ability for rogues to have.
• Stout Halfling: +1 Con. Being resistant to poison is good, but not nearly as great as Naturally Stealthy.

Human: +1 to every stat is more beneficial to a skill monkey class like the rogue than others, but even so you could still do better. No darkvision.

• Variant Human: +1 to two stats. Grab a skill and one of the recommended feats and go to town. No darkvision.

[/sblock][sblock=Player’s Handbook, Uncommon Races]Dragonborn: +2 Str and +1 Cha. As a Str-based rogue, you will likely need to multiclass or pick up a feat to improve your armor. These guys don't have darkvision and their breath weapon doesn’t even key off of one of their racial stats. Stay away.

Gnome: +2 Int, 25 ft speed, darkvision, advantage on all mental spell saves. Only one subrace is worth it.

• Forest Gnome: +1 Dex and the minor illusion cantrip. These guys make great Arcane Tricksters.
• Rock Gnome: +1 Con instead of Dex and worse subracial features. They should just go wizard instead.

Half-Elf: +2 Cha and +1 to two other stats. They have darkvision, two extra skills, one extra language, advantage vs charm saving throws and immunity to magical sleep. Excellent.

Half-Orc: +2 Str and +1 Con. Like the Dwarves, Half-Orcs are made to smash, not to sneak. For a Str-based rogue, you will want to multiclass or pick up a feat to improve your armor. At least Half-Orc rogues benefit from Darkvision, Relentless Endurance, and Savage Attacks.

Tiefling: +1 Int and +2 Cha. While thematically having a Tiefling rogue makes a lot of sense, mechanically it's a weak choice. Darkvision, fire resistance, and some spells don’t make up for a lack of an attack stat.[/sblock][sblock=Dungeon Master’s Guide Races]Aasimar: +1 Wis and +2 Cha. These shiny fellows are meant to be clerics or paladins, not rogues.

Eladrin: +2 Dex and +1 Int. All the base elf traits plus Misty Step 1/short rest and longbow proficiency. Perfect for becoming an Arcane Trickster. Misty Step pretty much functions as an upgraded Cunning Action(disengage & dash), allowing you to escape even from grapples or restraints and travel a bonus 30ft in any direction and across obstacles as a bonus action.[/sblock][sblock=Elemental Evil Player’s Companion Races]Aarakocra: +2 Dex and +1 Wis. Flight (at first level!) plus Cunning Action and/or the Swashbuckler's Fancy Footwork pretty much gives you a flyby attack, which is super. Just note that you can't Sneak Attack with your talons and that you will probably need your DM's permission to choose this race. No darkvision.

Genasi, Air: +2 Con, +1 Dex. Good stats, plus levitate once per long rest, and you can hold your breath forever. No darkvision.

Genasi, Earth: +2 Con, +1 Str. Pass without trace, once per long rest, and ignore rocky difficult terrain. You could probably make a Str-based rogue with this, with pass without trace making up for a low Dex score for stealth. No darkvision.

Genasi, Fire: +2 Con and +1 Int. Darkvision, fire resistance, some fire spells.

Genasi, Water: +2 Con and +1 Wis. Acid resistance, amphibious, swim speed, some water spells. No darkvision.

Goliath: Covered under the Volo's Guide to Monsters section.[/sblock][sblock=Sword Coast Adventurer’s Guide Races]Deep Gnome: +2 Int and +1 Dex. Great Arcane Trickster stats with 120ft Darkvision and situational advantage on Stealth. Same advantage on saving throws vs magic and 25ft speed as other gnomes. They also have access to a fantastic racial feat that grants at-will nondetection plus one casting of blindness/deafness, blur, disguise self each per long rest.

Duergar: +2 Con and +1 Str, superior darkvision, advantage on saves vs illusions and being charmed or paralyzed, enlarge/reduce and invisibility, sunlight sensitivity. Decent Str-based rogue.

Ghostwise Halfling: Core Halfling features, +1 Wis and telepathy. Solid, but no darkvision.

Half-Elf Variants: I measure these against full-blooded elves rather than against Half-Elves. With that mindset, Elves trade +2 Dex/+1 [x], perception proficiency, longbow proficiency, and trance for +1 Dex/+1 [x]/+2 Cha. Wood Elves get the worst deal as they have to choose between Fleet of Foot and Mask of the Wild.

• Half-Wood Elf: Fleet of Foot isn't worth it, but Mask of the Wild is good. Full-blooded Wood Elf is probably better, but this is still decent.
• Half-Moon/Sun (High) Elf Variant: Certain Cantrips are quite good (greenflame blade or booming blade come to mind). Your spellcasting stat is Intelligence.
• Half-Drow Variant: Drow Magic (faerie fire, specifically) without sunlight sensitivity, better than being a full-blooded Drow. Your spellcasting stat is Charisma.
• Half-Aquatic Elf Variant: Swimming speed is definitely not worth two skills. It doesn't even come with water breathing.

[/sblock][sblock=Volo’s Guide to Monsters Races]Aasimar: +2 Cha, darkvision, resist necro & radiant, heal action, light cantrip. Great package, just not for rogues.

• Protector: +1 Wis, 1 min flight & extra radiant damage per long rest.
• Scourge: +1 Con, 1 min radiant damage aura & extra radiant damage per long rest.
• Fallen: +1 Str, 1 min fear gaze & extra necro damage per long rest. Could work as a Str-based rogue.

Firbolg: +2 Wis & +1 Str. Detect magic or an improved disguise self per long rest, bonus action invisibility per short rest, and you can speak with critters & plants. Good abilities for a Str-based rogue, but no darkvision.

Goliath: +2 Str and +1 Con. Athletics proficiency and a once per short rest damage mitigator that doesn't scale. You could probably make a Str-based rogue with this, I guess, maybe. No darkvision.

Kenku: +2 Dex and +1 Wis. Forgery expert, 2 extra roguish skills, and sound mimicry make for a natural rogue, but no darkvision. The roleplaying sounds like a headache (incapable of creativity, can only speak by mimicking previously heard sounds).

Lizardfolk: +2 Con and +1 Wis. No attack stat, no way.

Tabaxi: +2 Dex and +1 Cha. Darkvision, limited double speed, climb speed, perception and stealth. Can’t ask for more.

Triton: +1 Str, +1 Con and +1 Cha. Amphibious, some water spells, and cold resistance. No good for most except maybe Str-based rogues, but no darkvision.[/sblock][sblock=Volo’s Guide to Monsters, Monstrous Races]Bugbear: +2 Str and +1 Dex. Darkvision, +5ft reach (!), stealth skill, and extra surprise damage. Awkward stats, but overall this is pretty sweet.

Goblin: +2 Dex and +1 Con. Small but still has 30ft speed, darkvision, limited minor extra damage vs larger foes, and bonus action disengage or hide (which is redundant for rogues). Good stats, but features are uninspiring.

Hobgoblin: +2 Con and +1 Int. Darkvision, two martial weapon proficiencies, a limited bonus to missed attacks/failed rolls. Not rogue material.

Kobold: +2 Dex and -2 Str (not a typo, that’s a minus). Small but still has 30ft speed, darkvision, limited ability to grant advantage to allies by groveling, and sunlight sensitivity. Even with the Dex and darkvision, kobolds are only for players who want to roleplay a serious underdog.

Orc: +2 Str and +1 Con. Darkvision, bonus action sprint (made redundant by Cunning Action) and intimidation. Mediocre Str-based rogues.

Yuan-Ti Pureblood: +2 Cha and +1 Int. Darkvision, suggestion, magic resistance(!), and poison immunity(!). Powerful package, just not for rogues. [/sblock][sblock=Unearthed Arcana Races (not legal in D&D Organized Play events)]Changeling (UA: Races of Eberron): +2 Cha and either +1 Dex or +1 Int. Proficiency in two social skills, 2 extra languages, 1 extra tool proficiency with double bonus (thieves tools is best), a defensive reaction ability, and the amazing Change Appearance action. Downsides are they don't get darkvision, can't Change Appearance into small size or change your clothing, and Unsettling Visage competes with Uncanny Dodge for your reaction.

Kalashtar (UA: Races of Eberron): +1 Wis, +1 Cha, and +1 other (pick Dex). Reaction to roll Wis saves with advantage, telepathy, advantage (but not automatic proficiency) with one social skill, and borderline-useless immunity to psychic damage and dream-related magic. No darkvision, but good stats, telepathy is great for sneaking, and advantage + Expertise + Reliable Talent is serious overkill for persuasion, or Insight for Inquisitive Kalashtars.

Minotaur (UA: Waterborne Adventures): +1 Str and +1 Str, Int, or Wis. Oddly enough, you can build a Str-based Arcane Trickster with this, if that strikes your fancy. Note that you can't Sneak Attack with your horns. No darkvision.

Revenant subrace (UA: Gothic Heroes): +1 Con, hp regen up to ½ health, free resurrection 24hrs after you die. This overwrites your previous subrace, so it’s best used with elves for their core Dex bumps and darkvision. There are also rules for using it with humans, dragonborn, and tieflings, but don’t. Talk with your DM to see if being a Revenant is right for you.

Shifter (UA: Races of Eberron): All shifters get +1 Dex, darkvision, Perception proficiency, and 1 minute of shifting (character level+Con bonus temp hp) per short rest.

• Beasthide: +2 Con, Athletics proficiency, and (+1d6 temp hp and +1 AC) while shifting. Great for melee rogues.
• Longtooth: +2 Str, Intimidation proficiency, and gain strength-based 1d6 bite attack while shifting. Can't Sneak Attack with the bite.
• Swiftstride: +1 Dex and +1 Cha, Acrobatics proficiency, +5 feet speed, and while shifting get additional +5 feet speed plus a reaction to move 10 feet away from adjacent enemies without triggering opportunity attacks. Awesome for ranged rogues, but for Scouts the reaction ability is made completely redundant by the Skirmisher ability.
• Wildhunt: +2 Wis, Survival proficiency, and while shifting get a fairly weak tracking ability. This is fine, I guess.

Tiefling (UA: That Old Black Magic): +2 Cha, darkvision.

• Abyssal: Same as vanilla tiefling.
• Infernal: +1 Con, spells randomly determined from a short list, increased hp. Not worth it.

Warforged (UA: Races of Eberron): +1 Con. +1 AC, advantage vs posion saves, resistant to poison damage, immune to disease, don't need to breathe or sleep, fully aware during long rests, and (for single classed rogues) AC = 11 + Dex + proficiency bonus. Wow!

• Envoy: +1/+1 to two ability scores of your choice, +1 skill proficiency, +1 tool proficiency, +1 language, doubled proficiency with one tool (Theieves Tools are best) that is integrated with your body. Double wow! Only downside is no darkvision.
• Juggernaut: +2 Str, strength-based 1d4 unarmed strikes, powerful build. Not for rogues.
• Skirmisher: +2 Dex, +5 feet speed, and move stealthily at full pace when traveling alone for over 1 hour (which is useless). No darkvision. Honestly, just pick the Envoy instead.

[/sblock][sblock=Plane Shift Races (not legal in D&D Organized Play events)]Aven (PS: Amonkhet): +2 Dex, 25ft walking speed, 30ft flying speed while not wearing medium or heavy armor. Flight is possibly the most contentious racial feature. Ask your DM if they'll allow it.

• Ibis-Headed: +1 Int, half proficiency bonus on non-proficient Int checks. Great for Arcane Tricksters, although Swashbuckler is also a strong choice as Flight+Fancy Footwork=Flyby Attack.
• Hawk-Headed: +2 Wis, Perception proficiency, and you don't have disadvantage on long range weapon attack rolls. I would never allow this in any game that I DM. Aside from the +2/+2, a precedent set by Mountain Dwarves, Flight combined with the long range buff lets Aven rain death down from 320ft in the air, which is ridiculously broken. 600ft if they get longbow proficiency from somewhere.

Khenra (PS: Amonkhet): +2 Dex, +1 Str, 35ft speed, proficiency with khopesh (i.e. longsword), spear & javelin, and either a conditional version of the Halfling's Lucky trait, or immunity to the frightened condition. I wouldn't allow these in my game as I'm not fond of immunity as a racial trait, but your DM might be more lenient.

Minotaur (PS: Amonkhet): These are essentially half-orcs that traded in their darkvision for a headbutt natural weapon. Fine for a Fighter, but not for a Rogue.

Naga (PS: Amonkhet): +2 Con, +1 Int, bonus action for conditional +5 speed, two natural weapons, poison immunity, poisoner's kit proficiency. Bad for Rogues, and IMO just badly designed.

Aetherborn (PS: Kaladesh): +2 Cha and +1 to two other stats, darkvision, necrotic resistance, intimidation proficiency, and two bonus languages. Almost as good as Half-Elves but with a very interesting flavour. Born from magical mishaps, these hedonistic creatures rarely live longer than a few years, so why waste time following the rules? I'd also give them the Trance trait, as the text says they don't sleep.

Vedalken (PS: Kaladesh): +2 Int and +1 Wis, advantage vs Int/Wis/Cha saves vs magic, and double proficiency bonus on Int checks about magic or technology. These stereotypical scientist-types are more or less medium-sized Rock Gnomes, better suited as Wizards (or Artificers, eventually) than Rogues.

Kor (PS: Zendikar): +2 Dex and +1 Wis, 30ft climb speed while not wearing heavy armor, Athletics & Acrobatics proficiencies, and the Halfling traits Lucky and Brave. These mountain dwellers would be perfect Thieves, if they had darkvision and if you can explain away their tradition-bound, community-oriented nature.

Merfolk (PS: Zendikar): +1 Cha, 30ft swimming speed, amphibious, one extra language. There are some weird game design choices going on with these emotionally detached fellows. In any event, they're probably better suited to the classes that they get their cantrips from.

• Emeria (Wind) Creed: +2 Wis, Deception & Persuasion proficiency, one druid cantrip.
• Ula (Water) Creed: +2 Int, navigator's tools & Survival proficiency, one wizard cantrip.
• Cosi (Trickster) Creed: additional +1 Cha & +1 Int, Sleight of Hand & Stealth proficiency, and one bard cantrip.

Vampires (PS: Zendikar): +2 Cha & +1 Int, darkvision, necrotic resistance, and a life-draining natural attack that can create your own zombie pets (called "nulls"). Rather than being undead "true" vampires, these living creatures were created/corrupted long ago with the need to feed by ancient otherworldly horrors. A neat spin on an old idea, but better suited to sorcerers or warlocks than rogues.

Goblins (PS:Zendikar): +2 Con, small, 25ft speed, darkvision, fire resistance, unarmored AC = 11+Dex. These impulsive rock-eaters aren't your traditional D&D goblin. They aren't any good either; they don't have a second ability score increase. Avoid.

• Grotag Tribe: Animal Handling proficiency.
• Lavastep Tribe: Advantage on stealth checks in rocky or underground terrain.
• Tuktuk Tribe: Thieves' tools proficiency.

Elves (PS: Zendikar): +2 Wis, no Trance, otherwise same as basic Elf

• Tanjuru Nation: +1 Cha, proficiency in two skills or tools of your choice.
• Joraga Nation: +1 Dex, otherwise same as Wood Elf. Still great, even without Trance.
• Mul Daya Nation: +1 Str, superior darkvision, sunlight sensitivity, chill touch, hex, & darkness spells, based on Wisdom. You could go Strength-based with these guys.

Human (PS: Innistrad): One extra language.

• Gavony Province: Same as basic Human.
• Kessig Province: +1 Dex & +1 Wis, Survival proficiency, 40ft speed (!), Dash action ignores difficult terrain, and when you melee attack a creature, it can't make opportunity attacks against you for the rest of your turn. Great for two-weapon fighting, although being a Swashbuckler accomplishes the same thing.
• Nephalia Province: +1 Int & +1 Cha, proficiency in four skills or four tools. The specific wording indicates that you choose ether skills or tools, so no mix-and-matching.
• Stensia Province: +1 Str & +1 Con, Intimidation proficiency, and +2 hp per character level. Decent Strength-based Rogues.

[/sblock]5. Backgrounds
Aim for two good skills, or one good skill and some nice extras. Note that if a character gains the same proficiency from two different sources, you can choose a different one of the same type (ie a skill or tool). This might make Backgrounds with redundant proficiencies marginally superior as they basically let you choose whatever skill or tool you want in exchange*.
[sblock=Player's Handbook Backgrounds]
Acolyte: Insight, Religion. Insight is good if you didn’t dump Wis, Religion is bleh, two extra languages can be a dud or a blessing depending on your campaign or DM, and the feature is very campaign specific (ie “What do you mean there isn’t a Temple of Waukeen in this town?”). Take this if you really want to play an agent of Shar/Tymora/etc for roleplaying.

Charlatan: Deception, Sleight of Hand. Two relevant skills, two relevant tools, 55gp worth of swag, and a fluff item like loaded die or signet ring. Sweet. The feature can be handy for forging DOA bounties for assassinations or warrants for search & seizures.

Criminal: Deception, Stealth. Two relevant skills. You already have proficiency in Thieves’ Tools so choose whatever tool you want to replace it. Criminal Contact could be useful for “find that guy” type quests or sending warning messages or something (“the orcs are coming, pass it on”), but I’d bet it’ll more often than not turn into a DM tool for delivering quests/plot info. Spy variant can legitimize your activities.

Entertainer: Acrobatics, Performance. One good skill, one okay tool kit & an instrument. One free instrument, costume, and 15 gp. This feature is actually pretty good. Can help advance plot as well as save money on lodgings. Less good if your DM regularly forgets to enforce such expenses. The Gladiator variant swaps the free instrument for an "inexpensive" weapon, but it doesn’t give you proficiency. So, no free whip proficiency for rogues unless your DM houserules it.

Folk Hero: Animal Handling, Survival. Bleh. Bad skills, bad tools, bad equipment. Only saving grace is the feature which nets you free safe houses to hide from local authorities or rivals. Robin Hood fluff is nice for roleplaying.

Guild Artisan: Insight, Persuasion. Two good skills (if you didn’t dump Wis), one language. Crafting mundane items is not generally worth it, but padlocks or manacles could be useful. Membership feature is DM-dependent for questing help, and won’t be of any help if there’s no nearby guildhall (“What do you mean there isn't a Scrivener Hall in this town?”). Another downside to this Background is that it actually costs you 5gp/month. Merchant variant can net you a free language and a mule & cart, and thematically it mixes better with the adventuring lifestyle.

Hermit: Medicine, Religion. This does nothing for you.

Noble: History, Persuasion. One good skill, one language. Feature can help get you into all the good parties. Just don’t blow your Sleight of Hand checks on the dance floor. Fluff can be interesting, playing as a bastard child or sliver tongued dandy. The Knight variant feature is poop.

Outlander: Athletics, Survival. Athletics is okay if you didn’t dump Str. While having a free trap can be nice at low levels, and the feature could potentially save your party on buying rations, nothing else here really speaks for you.

Sage: Arcana, History. Yeah, no.

Sailor: Athletics, Perception. Two decent skills, bad tools, some interesting swag. Too bad the free weapon doesn’t work with Sneak Attack. Ship’s passage can be nice depending on your campaign (note that Faerun is somewhat landlocked), but the variant Pirate could be so much fun (and so much trouble in the wrong player’s hand)! YMMV.

Soldier: Athletics, Intimidation. Two decent skills, land vehicle proficiency could potentially be useful, lackluster tool and equipment. Choose Officer or Scout and go bully the local town’s guard with your rank.

Urchin: Sleight of Hand, Stealth. Two great skills, one good tool, a free dagger, and a pet mouse (!). The feature is pretty bad though; it’ll be useful maybe once in your campaign and only then if you’re lucky.
[/sblock]
*You can create a custom background as per PHB p125. If so, choose any two skills, any two tools/languages, any equipment package, and whatever feature appeals to you. I'd recommend one that gives free food and/or lodgings (eg Entertainer, Folk Hero, Outlander) or political influence (eg Guild Merchant, Noble, Solider).

 

[clutchbone]

6. Rogue Class Features

Hit Points: d8. You are beefier than the mages, but that's not saying much. You may visit the front lines, but you definitely don't want to live there.

Proficiencies: Armor (Light). This is fine, I guess. Unless you went for a Str Rogue, medium armor isn’t worth it.

Weapons: All simple weapons plus hand crossbows, longswords, rapiers, & shortswords. This gets you every finesse weapon except the scimitar (aka slashing shortswords) & whip (aka slashing daggers with reach), so you’re good to go. Note that you cannot Sneak Attack with longswords so don't bother with them. Also, keep a sling in your backpack in case you ever need to bludgeon something. When building your rogue, you should decide if you prefer to fight in melee or at range.
[sblock=Melee vs Ranged]
Melee, Rapier – The simplest choice, works well with Cunning Actions. Hold a hand crossbow or throwing dagger in your off-hand for those turns when you can’t quite get into position. Cunning Action will help keep you safe by dancing in and out of melee. You sacrifice optimized damage for versatility.

Melee, Two Weapon Fighting – Two shortsword attack rolls equal two chances to land Sneak Attack, but it’s riskier as you won't be able to use Cunning Action to disengage in the same turn, unless you’re a swashbuckler archetype. This is tied with ranged for the most damaging choice (with Dual Wielder feat and 2 rapiers). While TWF allows more wiggle room in your build than ranged, it requires feats and/or multiclassing to really shine.

Ranged – Stay out of harm’s way while kill-stealing from (um, I mean focusing fire with) your meat shield. This is the safest choice and with the right race/feat (lightfoot halfling with Crossbow Expertise) it can be the most damaging if you gain advantage on attacks every turn via stealth. Other ranged builds may not do as much damage. Also remember that your meatshield may grant your enemy cover, so train your bruisers to fight to the side of the enemy where they won't block your line of fire, and/or multiclass for the Archery fighting style.[/sblock]
Tools: Thieves’ tools are the best tools. Unlock doors and disarm or set traps with them.
[sblock=Non-Class Tools]
Artisan’s tools: Only good for roleplaying.

Disguise Kit: This has wonky mechanics. Creating a disguise is an Int check with your tool proficiency bonus and passing off a disguise is a Deception check, so you need two different checks/proficiencies to make the most of disguises. Also, there are no rules for seeing through a physical disguise in the PHB, so talk with your DM. If your table resolves this issue, remember that you can disguise other characters too. Works well with certain Enchantment spells like Friends or Charm to protect your true identity from their anger at being manipulated.

Forgery: Draft fake bounties, deeds, warrants, and writs for fun and profit!

Gaming Set: This might come up during roleplaying, depending on your DM. Possibly uses include gambling with a powerful NPC for a favor or info, or ingratiating yourself into a seedy crowd, or to occupy someone and distract them from the real action, etc. You can probably use the deception or sleight of hand skills to cheat…

Herbalism Kit: You can spend 10 full days of downtime and 50gp to create an antitoxin or a potion of healing... or you can just buy them at the nearest town on your lunch break for the same price.

Musical Instrument: You're not a bard.

Navigator's Tools: If you're going anywhere by boat, the crew probably has their own professionals to take care of this.

Poisoners Kit: It takes 50gp and 20 full days of downtime to craft a basic poison with a piddly DC 10 Con save and 1d4 damage. The DMG has additional poisons, but they are too expensive off-the-shelf to be a regular addition to your arensal (if you can even find a seller), and it takes months of dedicated in-game time to craft most of them. At least using the kit to harvest poison from monsters is quick and free with no downside, but even this is dependant on what your DM throws at you.

Vehicles: Some parties make use of carts or wagons if their DMs are particular about encumbrance... after all, that dragon's hoard won't carry itself. [/sblock]
Saving Throws: Dex & Int. While every class gets one "good" save (Dex, Con, or Wis, targeted by the vast majority of effects) and one "bad" save (Str, Int, or Cha, targeted far less often), Int is probably the one that gets targeted the least. Only 3 spells (phantasmal force, symbol, feeblemind) and two monsters (Intellect Devourer, Mind Flayer) target Int, but to be fair those are nasty saves to fail. In comparison, roughly 90 monsters and 40 spells have a Dex-targeting component, so it's a good thing that Rogues get Evasion at lvl 7. You also get Wis proficiency at level 15, which is nice if you play at that level.

Starting Equipment: either go Rapier & shortbow, or 2x shortsword. Burglar’s pack is worth more gp so take it.

Skills: Unlike some other classes, every skill you will ever need is already on your class list. Unless there’s a Bard tagging along, you will probably be the resident skill monkey. If possible, try to fill gaps in your party's repertoire while sticking to your strengths. Choosing only four (plus two Background skills) can actually be pretty tricky, so you’ll probably end up basing your choices on your secondary stats, ie if you pumped Str then you’ll get Athletics, etc. The Expertise class feature (more on that later) can help you compensate for an average stat, so don't let a 10 or 12 hold you back.
[sblock=Rogue Class Skills]Acrobatics: A great choice. It uses Dex, comes up fairly often (ie to resist/escape a grapple, to avoid falling) and some DMs may let you use this instead of Athletics in certain situations.

Athletics: Climbing and jumping can be very common depending on your campaign, and Expertise can help make up for your mediocre Str. Thief archetypes will want this for their second story work. Others can safely ignore it, but I recommend Acrobatics if you do.

Deception: My personal favorite for getting out of (and into) trouble, but not every rogue needs to be good with words.

Insight: Someone in your party should have this, but it doesn't have to be you. Mandatory for Inquisitives.

Intimidation: This comes up often enough to be useful, especially if your party tends to capture the last baddie in any encounter for interrogation, but it tends to be riskier and gets less mileage than deception or persuasion.

Investigation: Arcane Tricksters and Inquisitives might want this, but as per the sidebar on pg. 178 you use Perception to find traps, not Investigation. This is for examining things, searching rooms, and looking for clues, so you'd think it'd work for trap finding, but apparently not. Ask your DM if they'd houserule trapfinding into this skill; it's reasonable based on the fluff.

Perception: This lets you “detect the presence of something”, like spotting traps or hidden foes, listening through doors, etc. Probably the most used skill in the game, and a great candidate for your Expertise if you are the group’s designated scout.

Performance: This isn't the bard handbook.

Persuasion: This comes up about as often as Deception, that is to say it comes up quite a lot. In my experience this is the lower risk/lower reward social option, with intimidation on the other end and deception in the middle.

Sleight of Hand: Thematically relevant, but YMMV. Not all rogues are pickpockets and anyways this can be very dangerous if you fail your roll, for you personally and for your party’s reputation/mission.

Stealth: You don’t have to take this, but you really should.[/sblock]
[sblock=Non-Class Skills]
Animal Handling: No thank you. Although a mounted rogue taking advantage of the Mounted Combat feat (using the mount as an adjacent ally for Sneak Attack) could be interesting.

Arcana: Thematic for an Arcane Trickster, but proficiency won’t come easy. Don’t bother.

History: Leave this to the bookworms.

Religion: Nope.

Medicine: Buy a Healer’s Kit. Or better yet, befriend a cleric.

Nature: You prefer alleyways and rooftops to grassland and forests

Survival: Leave this to the treehuggers.[/sblock]

Level 1. Expertise: Double proficiency on two skills (and two more at 6th level) is awesome. No worries if your ability score is low; this will effectively turn an 8 into a 12 for early level skill checks. By level 20, an Expertise skill with an ability score of 8 will have +11 on rolls, equal to a proficient skill with an ability score of 20! Note that while bards also eventually get this feature, only Rogues can choose Thieves Tools instead of a skill.

Level 1. Sneak Attack: Roll special damage dice in addition to your attack, if certain conditions are met*. Sneak Attack is fairly easy to take advantage of (pun very much intended), and the damage increases with your Rogue level. Limited to once per turn, so you can also Sneak Attack on another creature's turn (with Reaction Attacks, etc) in addition to your own. You won’t do as much damage as a greatsword-wielding meatshield, but there is something oddly satisfying about calling out "Sneak Attack!" at the table.

*Must: hit with a finesse or ranged weapon attack; have either 1) advantage on your attack roll, or 2) the target must have another non-incapacitated enemy within 5ft of it.
*Must Not: have disadvantage on your attack roll.

Level 1. Thieves’ Cant: This secret language is pretty much just for flavour. If you beg, your DM might work this into your campaign or allow your party members to know the Cant as one of their starting languages. Keep in mind that training in a new language after level 1 takes 250 days, which is probably never going to happen unless you do a "One Year Later" story break.

Level 2. Cunning Action: This is just plain awesome. Move in, stab, disengage, move out. Or shoot, move, hide. Just remember that the movement rules allow enemies to swing around your meatshield without triggering opportunity attacks so watch your positioning. You can also use Cunning Action to move a total of three times on your turn, making rogues (even Halflings and Gnomes) the 2nd fastest class after monks.

3. Roguish Archetype: See next section.

4. Ability Score Improvement: Better than most as you get 6 of these in total (at 4th, 8th, 10th, 12th, 16th and 19th). Only the fighter gets more.

5. Uncanny Dodge: Use your reaction to halve damage from one attack, as long as you can see the attacker. This stacks with resistance, if you have any. If so, apply Uncanny Dodge first. Less potent vs multiattackers, and won't work if you're blinded, if you're in the dark without darkvision, if the enemy is invisible/hidden, etc.

7. Evasion: How does one evade an exploding fireball, exactly? Who cares! You make your Dex save for half damage, you take zero damage instead. You fail that Dex save, you still only take half damage. Roughly 55% of Dex-targeting monster attacks and 75% of Dex-targeting spells are for damage, so Evasion sees a lot of use, and there's no limit to how often you can use it. Caution: Evasion doesn't apply vs effects that don't allow saving for half damage, such as disintegrate.

11. Reliable Talent: You can never roll lower than (10+modifiers) with your proficient skills. A skill monkey’s dream.

14. Blindsense: This feature isn’t usually available to player characters, which is cool. However, by the time enemies are this close it may be too late, and it might not work with Uncanny Dodge as you still can’t “see” them.

15. Slippery Mind: Rogues get training in Wisdom saves, buffing their traditional weakness vs mind-affecting spell and abilities. Too bad it’s so late in the game.

18. Elusive: This is pretty weak for an 18th level feature, although I guess it depends on how easy/common it is for monsters to get advantage on attacks at this level.

20. Stroke of Luck: Auto-hitting is nice, but at 20th level you’d think you’d be able to use it more than once per short rest, or at least let you be able to use it defensively and turn a hit against you into a miss. Oh well. Assassins might like this to ensure that their openers hit.

 

[clutchbone]

7. Roguish Archetypes
Thief
The Thief is your stereotypical rogue archetype with bonuses to stealing, climbing, and sneaking, as well as granting the old favorite Use Magic Device and the awesome Thief's Reflexes. While this archetype is stronger at higher levels rather than low, on the whole its effectiveness is about average when compared to the other options. Can't go wrong with it.
[sblock=Thief Features]
Fast Hands: Expanding your Cunning Action to cover Sleight of Hand, thieves' tools, and Use an Object actions. A DM may or may not let you pickpocket during a fight, although you may find using objects like ball bearings, poisons or potions as a bonus action to be handy. Works also with pouring oil, but not splashing it on someone as that's an attack roll (debated; ask your DM). Works very well with the Healer feat. See the sidebar on p.190 in the PHB for a non-inclusive list of other potential actions.

Second Story Work: The need to climb fast rarely comes up. The jumping bonus is so bad it might be broken: an extra 1-5 feet with 12-20 Dex only gets you 1 extra square, if you're using a map & minis, and is nigh-useless in the Theatre of the Mind playstyle.

Supreme Sneak: Advantage on stealth is fantastic, even at half speed, because the risks of a failed stealth check are often fairly dangerous. Wood Elves and Lightfoot Halflings especially will love this.

Use Magic Device: With magic items being rarer in 5e than in the past, there might not be many extra wands of fireball lying around for you to use. Still, few things are as frustrating as finding a magic item that no one in your party can use, so this helps with that.

Thief's Reflexes: Taking two turns is fantastic, and unlike Assassinate it works no matter how badly you roll your Initiative. Depending on the spread of rolls it's possible for you to get two turns in a row (ie if you go last normally, or if you're first and everyone else rolled terribly), potentially letting you Sneak Attack both times! [/sblock]
Assassin
This is your "finish the fight before it even starts" class, specializing in surprise round damage and disguise-type abilities. Personally, this archetype is a bit of a disappointment, but I imagine many players will pick it either because of a preoccupation with theoretical damage totals, or simply because being an assassin just sounds cool.
[sblock=Assassin Features]
Bonus Proficiencies: The only worthwhile use of the poisoner's kit is harvesting poison from dead monsters. Crafting takes too long and the off-the-shelf prices (if you can find a black market dealer that sells them) are too high for poisons to be practical otherwise. The Disguise Kit has its own issues; the rules regarding its use are ambiguous at best. Please see the "Non-Class Tools" section for more info.

Assassinate: Excellent combat opener - but that's all it is, a once-per-encounter ability that you often don't even get the chance to use. To make this work you've got to be stealthy (so you can surprise them) and perceptive (so no one surprises you), and make sure you Sneak Attack first and ask questions later! Assassins need darkvision, maxed initiative, attack, and stealth bonuses, the Alert feat, and multiple attack rolls (via two-weapon fighting, Crossbow Expert, etc) to make the most of this... as well as teammates that won't kick in the door before you're in position.

Infiltration Expertise: First, taking 7 days of downtime is a luxury that most campaigns can't afford, especially with pre-built campaigns. Second, you can't mimic an existing npc. Third, this is a great way to get separated from your party and die. Best case scenario is you leave the other players to play on their iPhones while you have a solo adventure, unless you can repeatedly find ways to sneak them in with you. ie "Hi, I'm a high ranking evil guy you've never heard of, arriving unannounced to inspect your evil lair. Please let me in, and also my friends too. Don't worry, they're cool."

Imposter: This explicitly doesn't work with Infiltration Expertise, which is dumb. Also, it'll be hard to gain 3 hours studying anybody besides your party members outside of the stereotypical Fancy Masquerade or a long boat ride or something.

Death Strike: This doubles ALL your damage, Sneak Attack, crit dice, static modifiers, poison, hex, whatever. You just have to make sure that 1) you surprise them, 2) you don't miss, and 3) the target fails it's Con save. Great in theory, probably rarely executed (tee hee hee) in practice. This works well with Stroke of Luck (if you ever end up playing at 20th level as a full-classed Assassin). [/sblock]
Arcane Trickster
Although the Arcane Trickster doesn't have the same damage dealing potential as some other Archetypes, it also doesn't have any truly bad features either. Since this archetype has two stats to keep up (Dex & Int), Arcane Tricksters have less space for feats. You'll often want to keep one hand free for spellcasting, so stick with either a rapier or hand crossbow, and don't invest in two-weapon fighting.
[sblock=Arcane Trickster Features]
Spellcasting: 1/3 spellcasting (as opposed to 1/2 casters like paladins and full casters like wizards) means you only get up to 4th level spells, although most players will only see spell levels 1-3. Still, the spells that you do get are great at making a Rogue's life easier. It's possible to dump Int and focus spells without saves or attack rolls (ie buffs, illusions), but not recommended as Magical Ambush and Spell Thief will suffer and your spell list isn't that large. After all, you only get to choose from Enchantment and Illusion spells (excluding cantrips and 1 spell each at 1st, 8th, 14th and 20th level) from the Wizard spell list, so you don't want to miss out on goodies like suggestion.

Mage Hand Legermain: A nice buff for a fun cantrip. Not having to risk your personal safety while pick-pocketing or disabling traps is great. Doing it as a bonus action is even better. Since mage hand is non-concentration, you can cast mage hand and then invisibility for maximum 1-minute mischief! You'll probably want to choose sleight of hand for one of your expertise skills to maximize this feature.

Magical Ambush: The other Archetypes get damage openers, you get this. This actually might be more useful since you can use it multiple times per encounter. Imposing disadvantage on a couple of suggestions for example can turn a deadly encounter into a cakewalk.

Versatile Trickster: A decent, if situational, source of automatic advantage and another nice buff for your mage hand. Note that this bonus action competes with Cunning Action (which includes moving the hand). If you have the Crossbow Expert feat, you will likely be using that bonus action instead.

Spell Thief: This functions as an alternative to counterspell. I wanted to rate this higher but unless mages in your campaign world run around shouting "lightning bolt!" your DM might require an Arcana check to determine what spell is being cast on you (eg if it is 4th level or lower), and that skill is not on your class list. Also, it's only once per long rest.[/sblock]
Spells
Tips for Picking Spells:
Sneak Attack does not work with cantrips (except a few from SCAG) or spells, so if you want to do damage just use a weapon.
You have an extremely limited number of spells, so try to pick ones that will see a lot of use rather than ones that are situational. You can't afford to pick niche spells.
Many spells of the same level compete with each other (ie color spray vs sleep, blur vs mirror image, crown of madness vs hold person vs phantasmal force vs suggestion), so don't bog down your spell list with four different spells that all boil down to "lock down a single target".

[sblock=Cantrips]
Acid Splash [Conjuration] (V,S) – Damage spell, so avoid. RAW, you can only target creatures, not objects, so no melting locks or ropes.

Blade Ward [Abjuration] (V,S) – 1 action, range self, for resistance against physical damage only, and it only lasts 1 round? No thanks.

Chill Touch [Necromancy] (V,S) – Damage spell, so avoid.

Dancing Lights [Evocation] (V,S,M; Concentration) – Concentration is bad. Creating magical floating torches isn’t a terrible choice, but it isn’t a good one either.

Fire Bolt [Evocation] (V,S) – Damage spell, so avoid. If you want to start fires just throw a regular torch or use prestidigitation.

Friends [Enchantment] (S,M; Concentration) – Restricting the target to a non-hostile creature and turning the target hostile afterwards are major detriments to an otherwise powerful cantrip, but it works great when you’re disguised as someone else.

Light [Evocation] (V,M) – This doesn’t require concentration, and you can use it offensively to mark a creature, but there are still better choices.

Mage Hand [Conjuration] (V,S) – It comes standard with Arcane Trickster and works with your class features.

Mending [Transmutation] (V,S,M) – Too situational to take up one of your slots, although you might be able use it to fix broken doors, locks or windows that got damaged during a burglary.

Message [Transmutation] (V,S,M) – Two-way secret communication with a range of 120 ft is very useful. You don't even need to know where the target is, exactly. "Somewhere that way, behind one of those bushes?" is good enough. Perfect for coordinating ambushes, jailbreaks, stealth missions, etc, or for just freaking out an NPC as the target doesn't automatically know who - or what - is whispering in it's ear.

Minor Illusion [Illusion] (S,M) – According to the Sage Advice column, this cantrip can either recreate a sound (including complex sounds like voices) or the image of a solid object, but not the image of a creature or an atmospheric effect like fog, and the image cannot be animated or be moved around. The creature part bugs me ("Fine, I create an image of a 'expertly sculpted and painted statue of a goblin'. Happy?"); it's weird that you can recreate a creature's voice but not its looks. Anyways, as always with illusions, effectiveness depends on player creativity and DM permissiveness. One solid use is creating a fake rock to hide in; casters can see through their own illusions, so it's great for ambushes.

Poison Spray [Conjuration] (V,S) – Damage spell, so avoid.

Prestidigitation [Transmutation] (V,S) – For me, this one is too much fun to pass up. Soil a rival's pants at a party (and then ambush him when he goes to change!), mark a target’s back for easy following in a crowd, flavor your fighter’s rations to taste like poop and yours to taste like fine cuisine, sell some pebbles to your fighter that taste like fine cuisine, clean off mud or blood from your clothes (if your DM won’t let you clean yourself 1 cubic foot at a time, then just take off your clothes and scrunch them into a ball), etc. There's so much fun to be had!

Ray of Frost [Evocation] (V,S) – Damage spell, so avoid.

Shocking Grasp [Evocation] (V,S) – Damage spell, so avoid. You have Cunning Action to disengage anyways.

True Strike [Divination] (S; Concentration) – This seems good, but the fact that it takes a whole action means that you can’t attack this turn, and you might lose the spell if your concentration breaks. Hiding with Cunning Action is a simpler method to get advantage without wasting your actions or cantrip selection. [/sblock][sblock=Cantrips, Sword Coast Adventurer’s Guide]Booming Blade [Evocation] (V,M) Hey, a cantrip that uses a melee attack with a weapon! You can Sneak Attack with this! Hit an enemy and they take thunder damage if they move. Pairs wonderfully with Cunning Action (Disengage), and even better with Fancy Footwork if you can find a way to give a Swashbuckler a cantrip. Thematically, "booming" anything seems kinds anti-Rogue and a no-go for stealth missions, but mechanically it's pretty awesome; it isn't even hampered by a weak Int score. Requires the Cast a Spell action, so can’t be used with opportunity attacks, two-weapon fighting, Extra Attack, etc. FYI, the Spell Sniper feat doubles this cantrip's range to 10ft, allowing reach with a whip.

Greenflame Blade [Evocation] (V,M) Hey, a cantrip that uses a melee attack with a weapon! You can Sneak Attack with this! Hit an enemy and spray fire on a second adjacent enemy. Fire is more commonly resisted than Booming Blade's thunder, but this is still great. Benefits from your Int mod, and requires the Cast a Spell action, so can’t be used with opportunity attacks, two-weapon fighting, Extra Attack, etc. FYI, the Spell Sniper feat doubles this cantrip's range to 10ft, allowing reach with a whip.

Lightning Lure [Evocation] (V) – Damage spell, so avoid.

Sword Burst [Conjuration] (V) – Damage spell, so avoid. [/sblock][sblock=1st level spells]
Charm Person [Enchantment] (V,S) – No concentration is good, although the target knowing it was charmed by you is bad. This can be used as an effective ambush spell, but otherwise don’t use it during combat. You can use this on a captured enemy as you are no longer fighting it, eliminating the need for interrogations. Also, it doesn’t necessarily know that you tried to charm it if it makes its save. Initial save only.

Color Spray [Illusion] (V,S,M) – This is good, but sleep is better. While this affects more hp, both the range and duration are shorter and you won't get to Sneak Attack the blinded targets before this wears off.

Disguise Self [Illusion] (V,S) – This is okay, but it won’t make a small Trickster look medium, or vice versa, and you can also just use a disguise kit.

Illusory Script [Illusion] (S,M; Ritual, Expensive Components) – This is way to situational.

Silent Image [Illusion] (V,S,M; Concentration) – Like minor illusion except this is much bigger and you can move it. Have fun!

Sleep [Enchantment] (V,S,M) - Your best combat spell at low levels, affecting an average of 22.5 hp as a 1st level spell with no save, and an additional ~9 hp for every slot higher (for a max of ~58.5 hp). You’ll probably want to retrain this out around level 5.

Tasha's Hideous Laughter [Enchantment] (V,S,M; Concentration) - Prone and incapacitated are powerful conditions (Sneak Attack!), although the target gets to make a save each turn and another save (with advantage) each time it’s damaged, so it won’t last long. Additional saves can be triggered by damage.[/sblock][sblock=2nd level spells]
Blur [Illusion] (V; Concentration) – Concentration on a defensive spell? So I can't cast other concentration spells and if I get hit I might lose the buff? Mirror image is better.

Crown of Madness [Enchantment] (V,S; Concentration) – This is useless if the target isn't adjacent to another enemy, and it takes up your action on subsequent turns.

Hold Person [Enchantment] (V,S,M; Concentration) – Suggestion has more utility and doesn’t allow a save each turn. However, auto-crit on Sneak Attack dice is very sweet. This is better if someone else casts it; at least then you might attack before the target has a chance to roll it's save again.

Invisibility [Illusion] (V,S,M; Concentration) – Redeem for one Sneak Attack.

Magic mouth [Illusion] (V,S,M; Expensive Components) – Way too situational.

Mirror image [Illusion] (V,S) – Yes please. Unlike blur this doesn't require concentration, although it does involve a bit of bookkeeping to track.

Nystul's magic aura [Illusion] (V,S,M) – Way too situational.

Phantasmal Force [Illusion] (V,S,M; Concentration) - Suggestion is better. Also, this spell suffers from too much TL;DR for a "take out one enemy" spell.

Suggestion [Enchantment] (V,M; Concentration) – Take out one enemy (“It's too hot to fight in plate armor, you should take it off and put it away”) or even two (“your buddy is making a mistake, grapple him before he hurts himself!”) that understands you for up to 8 hours. Initial save only. Some actions break spell, and the suggestion must "sound reasonable". Incredible utility, both in and out of combat.[/sblock][sblock=3rd level spells]
Fear [Illusion] (V,S,M; Concentration) - Take out a whole encounter, but in a dungeon be careful that they don’t run and alert others. Shorter range than hypnotic pattern but targets also drop their weapons and damage doesn't end the effect. Additional saves are end-of-turn and only happen if line of sight is broken, so it's better in open country.

Hypnotic Pattern [Illusion] (S,M; Concentration) - Take out a whole encounter, but damage breaks effect. Attack the affected targets one-by-one so they don't wake each other up. Take either this or fear. Initial save only.

Major Image [Illusion] (V,S,M; Concentration) – You can probably get by with just the first two illusions.

Phantom Steed [Illusion] (V,S; Ritual) - Not worth it with your limited spells, especially since you're not a ritual caster and it doesn't let more than one person ride.[/sblock][sblock=4th level spells]
Confusion [Enchantment] (V,S,M; Concentration) – Even if the enemy might attack you, it’s still better than them attacking you as normal. Decent AoE crowd control, but all the extra dice rolls can slow down the game.

Greater invisibility [Illusion] (V,S; Concentration) – As a rogue, you want to kiss whomever made this.

Hallucinatory terrain [Illusion] (V,S,M) – No thank you, how often will you really use this?

Phantasmal killer [Illusion] (V,S; Concentration) - Targets one enemy. Frightened condition is pretty good, and this is your only damage spell. Additional saves are at end of turn, as per official errata.[/sblock]Arcane Tricksters get to choose one non-illusion or enchantment wizard spell at 3rd, 8th, 14th, and 20th level. Try to pick spells that do something your other spells can't. Here are some suggestions, and try not to be overcome by analysis paralysis.
[sblock=Non-enchantment, non-illusion spell suggestions]
3rd: Escape spells (expeditious retreat, feather fall, fog cloud, longstrider), defensive buffs (protection from good & evil, shield), other (dectect magic, find familiar, grease)

8th: Buffs/debuffs (enlarge/reduce, levitate), movement (levitate, misty step, spider climb), other (rope trick)

14th: Buffs (haste), movement (fly)

20th: Escape (dimension door), crowd control (evard's black tentacles) [/sblock]
Mastermind (Sword Coast Adventurer’s Guide)
This is the silver-tongued schemer, built for intrigue. I really wanted to like this, as it represents the type of characters I most like to play, but the Mastermind is the weakest rogue archetype. Even for the specific type of campaign that would cater to the roleplay/interaction pillar of D&D, these features are mediocre at best.[sblock=Mastermind features]
Master of Intrigue: Proficiencies with the disguise kit, forgery kit, a gaming set, and 2 languages. Also, you can mimic accents and tics after 1 min of study. This is okay.

Master of Tactics: Use the help action as a bonus action with a range of 30ft, if the enemy can see or hear you. This precludes the use of Cunning Action and feats like Crossbow Expert, but it works well enough if you have a greatsword-wielding bruiser on your team and the initiative order lines up.

Insightful Manipulator: Outside combat, spend 1 min of study to learn if a creature has higher, equal, or lower Int, Wis, Cha or class levels than you, or perhaps some personal info. The usefulness of this is quite limited, in practice. So the target’s intelligence is higher than 10 and (like most NPCs) it doesn’t have class levels… now what?

Misdirection: Incredibly situational. If a creature (not a trap) attacks you (with a ranged or reach attack) while another creature (not an object) is granting you cover, you can use your reaction (instead of using it for Uncanny Dodge) to have the attack target the other creature (which might be your ally).

Soul of Deceit: You’re immune to unwanted telepathy and truth-enforcing/detecting magic, and you can trick telepaths with Deception. This would be okay… if it ever came up, and if you got it at a lower level, and if you could prevent the Aboleth or whatever from just scanning your meatshield instead of you.[/sblock]
Swashbuckler (Sword Coast Adventurer’s Guide)
The Swashbuckler is oriented around melee combat. Every Swashbuckler feature is both useful and thematically consistent, providing defense, offense, mobility and even some awesome battlefield control and out-of-combat utility. Remember that you still need a tank/meatshield to run interference. Works well with either strength or dexterity builds.
[sblock=Swashbuckler Features]
Fancy Footwork: Awesome mobility feature. This makes the Disengage action nigh-obsolete (except when you're adjacent to multiple foes), freeing up your bonus action for two-weapon fighting, Cunning Action(Hide), Elegant Maneuver, or other shenanigans. You can even target two different creatures with two-weapon fighting for maximum coverage. Note that it still works even if you miss.

Rakish Audacity: Initiative bonus? Sure I'll take one. Oh wait, there's something else... you can now Sneak Attack a creature if it’s the only one adjacent to you? Sweet! You’re no longer reliant on an adjacent ally or having advantage.

Panache: An action use Persuasion (ideally with Expertise, and eventually Reliable Talent) to draw aggro better than any tank, or to basically cast an upgraded, non-magical, at-will version of charm person. The only weaknesses are that you must share a language, and that this might get you killed.

Elegant Maneuver: Bonus action advantage on Athletics or Acrobatics checks. With Reliable talent and Expertise, you can use this to pretty much auto-escape any grapple. Combine this with Fancy Footwork for a vertical getaway after you stab the enemy (climbing and jumping in combat costs movement, not actions).

Master Duelist: Once per short rest, if you miss an attack, roll again with advantage. Slightly diluted version of your level 20 feature Stroke of Luck.[/sblock]
Inquisitive (Xanathar's Guide to Everything)
This is your detective-type rogue, in the vein of Robert Downey Jr.'s version of Sherlock Holmes. Favours wisdom as a secondary stat. It's a little less than average on the power scale.
[sblock=Inquisitive features] Ear for Deceit: You can't roll lower than an 8 on Wisdom (Insight) checks to sense if a creature is lying. This is fantastic… until you get Reliable Talent at 10^th level. Then Ear for Deceit becomes completely obsolete. Honestly, this is just a temporary prop for your Insightful Fighting feature.

Eye for Detail: Expands Cunning Action to include Wisdom (Perception) checks to spot a hidden creature or object, to make an Intelligence (Investigation) check to uncover and decipher clues, or to use Insightful Fighting (see below). Bonus action Insightful Fighting is the real purpose here.

Insightful Fighting: Bonus action, make a Wisdom (Insight) check vs the target’s Charisma (Deception) check. Win, and you can Sneak Attack it even without advantage or if no enemy is within 5 feet of it, but not if you have disadvantage. This benefit lasts for 1 minute or until you successfully use Insightful Fighting against a different target. They clearly built this subclass around this feature (see Ear for Deceit, Eye for Detail, Eye for Weakness), but requiring a bonus action and a skill contest really devalues it in my mind.

Steady Eye: Advantage on Wisdom (Perception) or Intelligence (Investigation) checks if you only move 1/2 speed or less. Picture the CSI agent that stands in the middle of the crime scene and takes it all in. With this, Reliable Talent, and Expertise, nothing gets past you.

Unerring Eye: Use an action to sense the presence of illusions, shapechangers, and deceitful magic within 30 feet of you. You can’t pinpoint what or where it is, but you know something is “off”. Unfortunately limited to [Wis mod] uses per long rest. Casters can learn the superior true sight spell two levels earlier, which is what they would do if you're playing in this kind of campaign.

Eye for Weakness: +3d6 on Sneak Attack with Insightful Fighting. Useful, if a bit underwhelming.[/sblock]
Scout (Xanathar's Guide to Everything)
Mobile rogue with a wilderness theme. The best rogue for kiting enemies with ranged weapons. Better at high levels.
[sblock=Scout features]Survivalist: Two extra skills (Nature & Survival) with doubled proficiency bonus, albeit ones that don’t typically see as much use in regular gameplay.

Skirmisher: Move up to half your speed as a reaction when an enemy ends its turn within 5 feet of you. This movement doesn’t provoke opportunity attacks. Skirmisher + regular move on your turn will put enough distance between you and the enemy to force them to dash to catch up or change targets, possibly saving you an attack next turn. If I'm being hit, I'd rather use Uncanny Dodge to mitigate damage and then use Cunning Action on my own turn to disengage, using the threat of my team's opportunity attacks to dissuade pursuit.

Superior Mobility: +10ft walking speed, and climb or swim speed if you have it. Sorry Aarakocras, no fly speed increase. This improves your Cunning Action (dash/disengage) and also Skirmisher.

Ambush Master: Advantage on initiative, and grant a round of advantage to allies vs the first creature you hit in the first round. The Alert feat will guarantee that you never lose out on using this.

Sudden Strike: Wow! Take the attack action, make an additional attack as a bonus action. If you target a different creature, you can Sneak Attack a second time, so do that. Currently the only way to Sneak Attack twice in the same turn. Overlaps a bit with the Crossbow Expert feat, if you have it.[/sblock]

 

[clutchbone]

8. Multiclassing

The first 8-13 levels of rogue are surprisingly rich with features and Ability Score Increases, depending on your archetype. This makes it a bit tricky to decide when level to multiclass, but in general any class feature that I've previously rated Blue or Skyblue is usually worth keeping in your build, as are ASIs. If you're going to multiclass, try to jump out before you hit a sub-par feature, or at least make an equal trade.

What You Lose When Multiclassing:

1 level dip: You lose nothing but a relatively weak capstone ability (1 auto hit/short rest).
2-3 levels: It's up to you if the trade-off is worth losing an Ability Score Improvement (you won't miss Elusive or 1d6 worth of Sneak Attack).
4 levels: You won't miss out on an ASI, but you lose a Roguish Archetype feature and 2d6 SA dice
5 levels: As above, but with a net loss of 1 ASI. Note that many classes get an Extra Attack at this level, which is very good.
6 levels: As above, but you also lose 3d6 SA and Slippery Mind (nooo!)
7 levels: As above, but you also lose Blindsense. Not a big deal.
8 levels: As above, but you also lose a Roguish Archetype feature and 4d6 SA.


Rogue/Barbarian
Become a Whirling Dervish, combining unconventional fighting styles with focused bloodlust. Surprisingly effective strength build.
Suggested build: Mountain Dwarf, Swashbuckler 15/Totem Warrior 5

Shield proficiency is nice, Unarmored defense is equal to or better than light armor, Reckless Attack works well with Sneak Attack and Fancy Footwork, Bear Totem resistance stacks with Uncanny Dodge, Danger Sense stacks with Evasion, and Extra Attack is always welcome.

Rogue/Bard
Become a Masquerader, ingratiating yourself with your victims while awaiting the perfect moment to strike.
Suggested build: Half-Elf Assassin 17/Lore Bard 3

As per Sage Advice, Reliable Talent & Jack of all Trades together let you take 10 on initiative checks (and also add 1/2 of your proficiency bonus), which is crazy good for assassinate/death strike. You also get four more proficient skills, two of which will have Expertise.

Rogue/Cleric
Become a Divine Blade, because your god's crusades are not always fought on a battlefield.
Suggested build: Wood Elf Assassin 12/War Cleric 8*

Clerics have a lot of effective low level buffs. Shield and whip proficiency is nice. Bonus action attacks (Wis mod) times per long rest is pretty sweet, and Channel Divinity (Guided Strike) gives +10 on an attack roll, very good for assassinate. Finally, Divine Strike helps offset the lost Sneak Attack dice, with +1d8 on a weapon attack, 1 use per turn, all day long.

*Trickery is a close second: more thematic, domain spells, & Cloak of Shadows = good. Blessing of the Trickster, poison Divine Strike = bad. Invoke Duplicity is okay, but competes with both Cunning Action & other concentration spells.

Rogue/Druid
Become a Skinchanger, using your animal forms to infiltrate areas that no humanoid could.
Suggested build: Thief 17/Moon Druid 3

Shield proficiency is nice, but you're mainly here for Wild Shaping for sneaking around in mouse/lizard/etc form with your rogue skill modifiers. It's a shame you can't sneak attack with beast attacks.

Rogue/Fighter
Become a Swordmaster, defeating your challengers with unrivaled skill and perfect form.
Suggested build: Variant Human Swashbuckler 12/Battlemaster 8

Fighting Styles are awesome (Two-Weapon Style works great with Fancy Footwork), Riposte maneuver lets you Sneak Attack as a reaction, Extra Attack is always good, and you can end up with seven ASI's (full class rogues get six) if you go with the recommended Rogue 12/Fighter 8 spread. If the Battlemaster's maneuvers seem like to much paperwork for you, Champions are also surprisingly good for Improved Criticals; crits double Sneak Attack dice! With Xanathar's Guide To Everything, Arcane Archers are decent for ranged rogues, while Samurai pair very well with Swashbucklers.

Rogue/Monk
Become a Ninja, mixing pressure-point attacks with mystic traditions to neutralize your enemies from the shadows.
Suggested build: Half-elf Assassin 14/Shadow Monk 6

While this seems like it should be an ideal pairing, Monk and Rogue don't mesh well. Martial Arts, Ki points, Unarmored Movement, Deflect Missiles, and Slow Fall all scale with your total monk levels, so multiclassing hurts you there. You cannot Sneak Attack with unarmed strikes, which lessens the value of Flurry of Blows. Cunning Action is superior to Step of the Wind, and Deflect Missiles conflicts with Uncanny Dodge, although can theoretically Sneak Attack with returned missiles off-turn. Really the only things here for you are Unarmored Defense+Unarmored Movement, Extra Attack, and Shadow Step; bonus action teleports within dim light/darkness + auto advantage goes great with Sneak Attack. Just remember that attacking in darkness without darkvision will negate Sneak Attack.

Rogue/Paladin
Become an Inquisitor, rooting out and eliminating heretics, acolytes of rival deities, and unholy abominations.
Suggested build: Assassin 12/Vengeance Paladin 8

Lay on Hands, spell slots, and Divine Smite (via spell slots) all scale with your paladin level, making them less effective for a multiclass character. However, shield proficiency, Dueling fighting style, Extra Attack, and Aura of Protection are all great. The real draw here is Vow of Enmity from the Vengeance oath for auto-advantage vs 1 enemy per short rest.

Rogue/Ranger
Become a Vagabond, traveling the world and surviving however you can.
Suggested build: Thief 15/Gloom Stalker 5

Favored Enemy & Natural Explorer are weak, as is the whole Beastmaster subclass. The hunter's mark spell, proficiencies with shields/longbows/whips/heavy crossbows, a Fighting Style, and extra attack are good, but the Gloom Stalker (from Xanathar's Guide to Everything) is amazing. Extra attack, movement, and damage in the first round with no conditions, plus darkvision! This single-handedly eliminates the major drawback for many race choices, having disadvantage on attack rolls in darkness invalidate your sneak attack.

Rogue/Sorcerer
Become a Hedge Mage, using your street smarts and natural magics to confound your foes.
Suggested build: Thief 17/Draconic Sorcerer 3

The double proficiency on Cha checks vs dragons is mutually exclusive with Expertise, but extra hp is always welcome, and the base AC modifier is equal to wearing a suit of +1 studded leather, so that's nice. However, Sorcery points are based on sorcerer level, so this is bad for a multiclass character. For Metamagic, Quickened Spell works with the attack action, Subtle Spell is quite thematic, and Twinned Spell gives you great bang for your buck.

Rogue/Warlock
Become an Occultist, signing fell contracts with dark powers to further your pursuit of wealth and influence.
Suggested build: Half-elf Swashbuckler 11/Blade Pact 9 (Hexblade)

Hex is your new best friend. Impose disadvantage on Wis check to spot you or Dex checks to hinder their initiative rolls.[sblock=Patron]
Archfey: Adds some useful save-or-suck spells (faerie fire is the real draw for AoE auto-advantage) and some illusions. Gain a short range AoE charm/frighten ability, but note that it can affect allies too. Unlike the charm person spell, targets do not know that they were charmed by you, so there's plenty of opportunity for RP abuse here. At 6th level, Misty Escape might compete with Uncanny Dodge for your reaction, but it applies to any damage, not just attacks, it sets up Sneak Attack, and it foils multiattackers.
Fiend:
Fiend: Adds mostly damage spells and some save-or-sucks. Gain Cha+warlock level temp hp whenever you kill a hostile creature. Less effective for multiclass rogues with unmaxed Cha. At 6th level, Add 1d10 to any of your ability checks or saving throws. This includes initiative rolls and death saving throws.
Great Old One: Adds save-or-suck spells (tasha's hideous laughter makes one enemy prone for melee Sneak Attacks) and some divination. Gain 30ft one-way telepathy. Ask your DM how this works with social skills like Deception or Intimidate. At 6th level, Entropic Ward competes with Uncanny Dodge for your reaction, but it has a chance to set up Sneak Attack.
Hexblade (Xanathar's Guide to Everything): Charisma as your attack stat, medium armor, shields, proficiency with the few finesse weapons you're missing, Hexblade's Curse... all at level one. Holy crap! The single best multiclass option for melee rogues, hands down. [/sblock][sblock=Pact Boon]
Chain: Have your familiar use the Help action to set up Sneak Attack. Help action doesn't break invisibility, so choose an Imp or Quasit, or Sprite if you're good.
Blade: Smuggle your rapier into any location. Bonus points if you use it to steal someone's ancestral weapon out of their keep.
Tome: Learn any three cantrips. I strongly recommend Guidance and either Booming Blade or Greenflame Blade, if you don't have them already.[/sblock][sblock=Invocations]
Beguiling Influence - gain proficiency in Deception and Persuasion
Book of Ancient Secrets - you can learn and cast any ritual you buy or find, regardless of class requirement. Top choice for Tome warlocks.
Devil's Sight - Humans and other night-blind races will want this, but everyone can pair it with darkness to confound enemies - and allies - to great effect.
Fiendish Vigor - 1d4+4 temp hp as an action. Use before every fight. Only useful at low levels so replace it eventually.
Mask of Many Faces - thematic but weak, especially for small pcs as they can't use this to look medium sized.
Misty Visions - silent image at will! So much fun to be had. Top choice.
One With Shadows - works well with Sneak Attack and ambushes, but it costs an action to use and you can't move.
Voice of the Chain Master - might be fun, but there are better choices.
Thirsting Blade 5th blade pact - two attacks on attack action. Top choice and the main reason for a Rogue to go Blade Pact.
Improved Pact Weapon (XGtE): Pact weapon is your spellcasting focus, becomes a +1 magic item, and can be a ranged weapon. Charisma-based ranged attacks! [/sblock]
Rogue/Wizard
Become a Magician, improving your skills in both sleight-of-hand and magic with constant practice and study.
Suggested build: Arcane Trickster 13/(Divination, or Bladesinging) 7

Spellcasting - You'll want to max your Dex first, but Int comes right after. See the Arcane Trickster section for advice on spell selection.
Arcane Recovery - This can recover your Arcane Trickster spells too! Works best with an odd-numbered amount of wizard levels.[sblock=Arcane Tradition]
Arcane Tradition, 2nd level
Abjuration - the prevented damage scales with wizard level. Trigger it with Shield and stack it with False Life.
Conjuration - You can use this feature to create a dagger, crowbar, telescope, key (although it might take weeks to guess the right shape), stepladder... use your imagination. Errata: "The conjured object also disappears if it deals any damage", so one stab and your conjured dagger goes *poof*.
Divination - Portent is the best school feature, at any level. Replace any d20 roll on any creature you can see with a pre-rolled d20, 2/day. Doesn't work if you're blinded, though.
Enchantment - Unlike the Charm spell, targets do not know that they were charmed by you, so there's plenty of opportunity for RP abuse here, but the 5ft limit is crippling.
Evocation - I advise using weapons for damage (and Sneak Attack) and spells for everything else, so don't choose Evocation.
Illusion - Learn 1 more cantrip and buff your minor illusion. Great for ambushes or distractions.
Necromancy - This only works when you kill creatures with spells, not weapons. Pass.
Transmutation - Scam merchants with solid bars of "silver", then skip town. Turn an iron lock into wood, then set it on fire. Be creative.
Bladesinging (Sword Coast Adventurers Guide) - 1 min buff to AC, speed, acrobatics, & concentration checks. Twice per short rest. Great for melee rogues. Restricted to elves, unless your DM says otherwise.
War Magic (Xanathar's Guide to Everything): The reaction bonus to failed saving throws is nice, as is the bonus to initiative.

Arcane Tradition, 6th level
Abjuration - Call me selfish (I don't care, I'm a rogue!), but I'd rather spend my class features on myself and not others.
Conjuration - Teleporting 30ft as an action is okay for "oh no!" situations like being grappled, and swapping places with your meatshield can be a lifesaver.
Divination - This is kind of like having a subsidy for casting Divination spells, which you otherwise might avoid using in favor of saving slots for combat.
Enchantment - This works best if there are either two enemies and no allies nearby (in which case good luck to you), or vs ranged attacks which will probably target an ally instead.
Evocation - I advise using weapons for damage (and Sneak Attack) and spells for everything else, so don't choose Evocation.
Illusion - Use your action to edit your existing illusion. This would be better if you could use your reaction as well to adapt to monster actions. Oh well.
Necromancy - There are plenty of ways to abuse this.
Transmutation - This is really nice. Proficiency in Con Saves is probably the best choice to keep "always on", but darkvision is good for humans.
Bladesinging (Sword Coast Adventurers Guide) Extra Attack. EA is generally better than greenflame or booming blade (two chances to land a Sneak Attack and/or a critical hit > somewhat conditional extra damage), so don't use up your cantrip choices with those if you're going to get this. Restricted to elves, unless your DM says otherwise.
War Magic (Xanathar's Guide to Everything): Bonus spell damage is wasted on rogues.[/sblock]

 

[clutchbone]

9. Feats

[sblock=Player's Handbook Feats]
Actor: Arcane Tricksters, Assassins, and Masterminds all have class features/spells for mimicking others, and the bonus to disguises is situational.

Alert: These perks are useful for any class, really, but the +5 to Initiative is pretty much mandatory for Assassins.

Athlete: Thieves already get the climbing bonus, and the rest isn't really worth it.

Charger: This interferes with your Cunning Action to disengage to safety.

Crossbow Expert: Lets you ignore the loading property so you can draw ammunition as part of the attack. Taken with the feat's third property, a rogue armed with a hand crossbow can fire twice in one turn, although you need one hand free to handle the ammo. One of the few ways a rogue can get multiple attack rolls (without multiclassing for 5 levels).

Defensive Duelist: This can potentially be one of the best defensive feats at high level, but note that it competes with Uncanny Dodge for your reaction, it only protects against one melee attack per round, and it also doesn't protect against critical hits. If your DM rolls dice in the open and you don't mind the overlap, you can use this for regular hits and Uncanny Dodge for crits to save a lot of damage.

Dual Wielder: Remember, if you take this to optimize melee damage, you won't be able to use Cunning Action to disengage behind your meatshield. Better for Swashbucklers as they can use Fleet of Foot instead.

Dungeon Delver: This is dependent on your campaign (and DM); fighting a horde of orcs? You don't need this. Raiding tombs? Might be a good idea. Arcane Tricksters can just use their Mage Hand to avoid trap damage entirely.

Durable: Normal hit die recovery for rogues is ~4.5+Con. Con is usually +1 or +2 for rogues, so this benefit will turn your avg hit die recovery to ~5+Con or ~6+Con. Not worth it.

Elemental Adept: You don't ever use elemental damage spells.

Grappler: There's an interesting Grappling Rogue build, but it's more like a dip into rogue than a full rogue build. Everyone else should avoid.

Great Weapon Master: You can't Sneak Attack with these.

Healer: This actually isn't that bad. Healer's Kits heal more hp per shot than a potion of healing and are also much more cost efficient (about 7 copper per hit point healed without even factoring the number of hit dice, vs about 7.1 gold per hit point with the potion). This feat ends up saving the party lots of gold over the long run, and Healer's Kits are also more common than magical potions. Better for Thieves with their Fast Hands & Cunning Action(use an object) features.

Heavily Armored: Maybe a Str-based Mountain Dwarf rogue would consider this, but they should really just dip into fighter instead.

Heavy Armor Master: No, this is too far even for the Mountain Dwarf.

Inspiring Leader: Meh, this isn't really your bag of tricks.

Keen Mind: Just straight bump Int instead, if you feel the need.

Lightly Armored: Worthless to you.

Linguist: Just straight bump Int instead, if you feel the need.

Lucky: Another feat that's universally useful for any class. Note that this doesn't grant advantage, just an extra d20, so it doesn't work with Sneak Attack.

Mage Slayer: Boost your melee damage output and saving throws vs adjacent spellcasters, including innate (and psionic) ones. Swashbucklers have an easier time fulfilling Sneak Attack conditions behind enemy lines, where the casters usually hide. Note that the reaction attack resolves after the triggering spell is cast (DMG p. 252), so a spell like shocking grasp can prevent your special melee attack from happening.

Magic Initiate: Get hex and don't look back. The target won't know you've placed a hex on it (pg. 204) so casting this from hiding won't break surprise, and since initiative counts as a dexterity check this is great for Assassins to set up assassinate/death strike! Hex can also last multiple encounters (as long as you don't travel or take a short rest) because you can re-target it anytime after the initial target dies within the 1 hour duration. If you prefer a divine flavor, guidance, resistance and bless are solid selections from the cleric list; you don't even need any Wis to make them work. There's also find familiar; choose an owl to get a flying scout and the flyby help actions.

Martial Adept: 1 maneuver per short rest isn't that great. If you do take this, go with Precision and Riposte.

Medium Armor Master: Str-based Mountain Dwarf rogues or multiclass rogue/fighters may want this, but no one else.

Mobile: +10 speed is good for small rogues, but you already have Cunning Action to disengage, unless you really want to make the most of TWF.

Moderately Armored: You're here for the +2 AC from shield proficiency, or if you happen to find mithral half-plate armor. You could also just multiclass into fighter.

Mounted Combatant: Having automatic advantage on melee attack rolls is great on paper, but most campaigns will probably require you to become unmounted fairly regularly. Also as a rogue you generally don't want to encourage attackers to target you.

Observant: If you have proficiency and Expertise in perception, this can be potentially game breaking in your DM's eyes. If not, this can still be useful. Note that this adds a modifier to your passive score only, not to any actual rolls.

Polearm Master: Nope. No Sneak Attacks with two-handed weapons.

Resilient: Choose Con and by 15th level you will be proficient in all 3 big saves. This works best if your character starts off with an odd Con stat.

Ritual Caster: If you take this, choose wizard (as they have the most ritual spells) and get find familiar and an owl (flyby attack + help action = advantage). I prefer Magic Initiate, but this is fine.

Savage Attacker: No, re-rolling one d8 (at best) is really weak for a feat.

Sentinel: On paper, more opportunity attacks = more Sneak Attacks (as long as SA conditions are met), however this is quite risky as monsters will probably just end up focusing on you. Great if your party has a way of directing who your enemy attacks (ie Goading Attack maneuver, etc). Remember that Sentinel attacks resolve after the triggering attack (DMG p. 252) so you can only avenge your friend's death, not prevent it.

Sharpshooter: Excellent when paired with Crossbow Expert to extend the hand crossbow's paltry range. Also works well for Assassins with Skulker. This way your assassinate/death strike will do plenty more damage with less risk if you miss.

Shield Master: This lets you shove(knock prone) as a bonus action before your attack to set up Sneak Attack conditions, but you need to grab proficiency with shields from somewhere first. For best results you should be a strength-based rogue trained in Athletics with Expertise while abusing Reliable Talent.

Skilled: Ehhh, not really necessary. You already get at least 6 skills at the minimum.

Skulker: Pretty decent for sniping. There's a bit of overlap though for Wood Elves and Lightfoot Halflings. I'd usually just take Crossbow Expert or Sharpshooter, unless I was playing an Assassin - missing with an assassination opener is frustrating, but at least they won't know where you are, and you might even get to try again if they didn't hear the arrow.

Spell Sniper: You can't use ranged spells with Sneak Attack.

Tavern Brawler: You can't Sneak Attack with improvised weapons or unarmed strikes.

Tough: More hitpoints are always welcome, but it's best for rogues to focus on other areas (like how not to get hit at all)

War Caster:Only for Arcane Tricksters, and even then it's not a top priority. Full casters get more use out of this feat than you.

Weapon Master: Heavy crossbows, longbows, scimitars and whips aren't worth the price of a feat. For what it's worth, whips are the best choice here. [/sblock][sblock=Xanathar's Guide to Everything Racial Feats]Bountiful Luck (Halfling): Moderately useful for any halfling adventurer, and halfling adventurers make good rogues.
Dragon Fear (Dragonborn): Poor race choice for rogues.
Dragon Hid (Dragonborn): Poor race choice for rogues.
Drow High Mage (Drow): Useful spells using charisma.
Dwarven Fortitude (Dwarf): Poor race choice for rogues.
Elven Accuracy (Elf or Half-elf):As you should already be sniping with advantage from hiding, this is amazing.
Fade Away (Gnome): Excellent for forest gnome rogues. Works well with both Sneak Attack and an Arcane Trickster's Magical Ambush feature.
Fey Teleportation (High Elf): Supercharged misty step is great for Arcane Tricksters.
Flames of Phlegethos (Tiefling): Poor race choice for rogues, and rogues can't Sneak Attack with spell damage.
Infernal Constitution (Tiefling): Poor race choice for rogues.
Orcish Fury (Half-orc): Poor race choice for rogues.
Prodigy (half-elf, half-orc, or human): Skill, tool, language, and expertise? *Skill monkeying intensifies*.
Second Chance (Halfling): Pretty good, but some overlap with Uncanny Dodge.
Squat Nimbleness (Dwarf or a small race): Dex, speed, skill, and adv. to escape grapples is quite a good package for halflings and gnomes.
Wood Elf Magic (Wood elf): Pass without trace + expertise & reliable talent is very powerful.
[/sblock]

Example Builds

For these builds I have only included items where choice is a factor, so basic class and achetype features are not shown. Also they are meant to be examples of capable solo-class builds and therefore are not multiclassed, except for the strength build which needed a bit of help.
[sblock=Thief Build]
This is your classic treasure-seeking, trap-finding, dungeon-delving Thief. He's the penultimate scout, able to walk into any room and notice every little detail without trying; by level 20, he will have 30 passive perception which is 2 points shy of the theoretical maximum.
Race: Variant Human (Dex +1 Wis +1, Skill: Perception, Feat: Observant(Wis), Language: Orc)
Ability Score Array: Str 12, Con 13, Dex 16, Int 10, Wis 16, Cha 8
Background: Urchin
Proficient Skills: Acrobatics, Athletics, Insight, Investigation, Perception, Stealth, Sleight of Hand
Level 1: Expertise: Perception, Stealth
Level 2:
Level 3:
Level 4: Ability Score Improvement: Dex +2
Level 5:
Level 6: Expertise: Athletics, Thieves Tools
Level 7:
Level 8: Ability Score Improvement: Healer feat
Level 9:
Level 10: Ability Score Improvement: Dex +2
Level 11:
Level 12: Ability Score Improvement: Dungeon Delver feat
Level 13:
Level 14:
Level 15:
Level 16: Ability Score Improvement: Resilient(Con) feat
Level 17:
Level 18:
Level 19: Ability Score Improvement: Lucky feat
Level 20:
[/sblock]
[sblock=Assassin Build]
This Assassin is a ranged damage specialist and party "face". She is built to obtain a surprise round and/or high initiative and capitalize on her damaging 1st round Assassin features, preferably by sniping from ambush or from behind her allies.
Race: Lightfoot Halfling
Ability Score Array: Str 8, Con 12, Dex 17, Int 8, Wis 15, Cha 14
Background: Criminal
Proficient Skills: Deception, Insight, Intimidation, Perception, Persuasion, Stealth
Level 1: Expertise: Insight, Stealth
Level 2:
Level 3:
Level 4: Ability Score Improvement: Crossbow Expert feat
Level 5:
Level 6: Expertise: Deception, Intimidate
Level 7:
Level 8: Ability Score Improvement: Dex +1, Wis +1
Level 9:
Level 10: Ability Score Improvement: Alert feat
Level 11:
Level 12: Ability Score Improvement: Dex +2
Level 13:
Level 14:
Level 15:
Level 16: Ability Score Improvement: Sharpshooter feat
Level 17:
Level 18:
Level 19: Ability Score Improvement: Skulker feat
Level 20:
[/sblock]
[sblock=Arcane Trickster Build]
This Arcane Trickster is a jack-of-all-trades, providing decent ranged support, social skills, and magical tomfoolery. I'm a bit biased though, as this was my very first 5e character. Man, I miss this guy.
Race: Forest Gnome
Ability Score Array: Str 8, Con 13, Dex 16, Int 17, Wis 8, Cha 12
Background: Charlatan
Proficient Skills: Acrobatics, Deception, Investigation, Persuasion, Stealth, Sleight of Hand
Level 1: Expertise: Deception, Stealth
Level 2:
Level 3:
Level 4: Ability Score Improvement: Crossbow Expert feat
Level 5:
Level 6: Expertise: Persuasion, Sleight of Hand
Level 7:
Level 8: Ability Score Improvement: Dex +2
Level 9:
Level 10: Ability Score Improvement: Magic Initiate feat (Wizard): friends, mending, find familiar,
Level 11:
Level 12: Ability Score Improvement: Con +1, Int +1
Level 13:
Level 14:
Level 15:
Level 16: Ability Score Improvement: Dex +2
Level 17:
Level 18:
Level 19: Ability Score Improvement: Int +2
Level 20:
[/sblock][sblock=Spell Choices by Level]
Level 1:
Level 2:
Level 3: greenflame blade, message, prestidigitation, shield, silent image, sleep
Level 4: charm person
Level 5:
Level 6:
Level 7: mirror image, replace charm person with suggestion
Level 8: misty step, replace sleep with invisibility
Level 9:
Level 10: friends, hold person
Level 11: disguise self
Level 12:
Level 13: hypnotic pattern, replace disguise self with major image
Level 14: blink
Level 15:
Level 16: phantom steed
Level 17:
Level 18:
Level 19: confusion, replace phantom steed with greater invisibility
Level 20: dimension door

Known spells at level 20:
Cantrips: minor image, mage hand, message, friends, mending, prestidigitation, greenflame blade,
1st level: shield, silent image, find familiar
2nd level: hold person, invisibility, mirror image, misty step, suggestion,
3rd level: blink, hypnotic pattern, major image,
4th level: confusion, dimension door, greater invisibility.
This is a solid mix of offense and defense across all spell levels.[/sblock]
[sblock=Strength-Based Thief Build]At first I was skeptical, but you can definitely build a decent rogue that uses Strength for attacks. This rogue is a textbook hired goon, adept in shaking down, roughing up, and ransacking. Instead of sneaking around, this bruiser eventually masters the art of knocking enemies prone with a shield and then Sneak Attacking them while they lie in the dirt. The one fighter level is for shield proficiency.
Race: Mountain Dwarf
Ability Score Array: Str 17, Con 15, Dex 15, Int 8, Wis 10, Cha 10
Background: Criminal
Proficient Skills: Athletics, Insight, Intimidation, Perception, Stealth, Sleight of Hand
Level 1: Expertise: Athletics, Intimidation
Level 2:
Level 3:
Level 4: Ability Score Improvement: Str +1, Dex +1
Level 5:
Level 6: Expertise: Insight, Perception
Level 7:
Level 8: Multiclass: Fighter (Dueling fighting style)
Level 9: Ability Score Improvement: Shield Master feat
Level 10:
Level 11: Ability Score Improvement: Str +2
Level 12:
Level 13: Ability Score Improvement: Resilient(Con) feat
Level 14:
Level 15:
Level 16:
Level 17: Ability Score Improvement: Medium Armor Master feat
Level 18:
Level 19:
Level 20: Ability Score Improvement: Con +2[/sblock]
[sblock=Swashbuckler Build]
This Swashbuckler is a decent party face and skill monkey with high charisma, 3 languages, and 8 skills. At mid-level, she's great at slipping through enemy ranks to take down enemy spellcasters, thanks to her archetype features and the Mage Slayer feat. She becomes a lot beefier in the epic levels, perfect for staying alive in melee while dishing out pain with dual rapiers. Although she's fine as is, a one-level dip into Fighter for whip proficiency and Two-Weapon fighting style would be ideal.
Race: Half-Elf (Dex +1 Con +1 Cha +2, Skills: Acrobatics, Persuasion, Language: Goblin
Ability Score Array: Str 10, Con 15, Dex 16, Int 8, Wis 10, Cha 16
Background: Sailor
Proficient Skills: Acrobatics, Athletics, Deception, Insight, Intimidation, Perception, Persuasion, Stealth,
Level 1: Expertise: Persuasion, Stealth
Level 2:
Level 3:
Level 4: Ability Score Improvement: Dex +2
Level 5:
Level 6: Expertise: Athletics, Deception
Level 7:
Level 8: Ability Score Improvement: Dual Wielder
Level 9:
Level 10: Ability Score Improvement: Dex +2
Level 11:
Level 12: Ability Score Improvement: Mage Slayer feat
Level 13:
Level 14:
Level 15:
Level 16: Ability Score Improvement: Resilient(Con) feat
Level 17:
Level 18:
Level 19: Ability Score Improvement: Cha +2
Level 20: [/sblock]

 

[clutchbone]

Reserved.

 

[clutchbone]

Reserved

 

[Zardnaar]

Tips, Tricks & Combos

Always try to gain advantage, even if your target already has an adjacent ally. Increasing your odds to hit will increase your damage output.
Sneak Attack doesn't necessarily require an ally to be adjacent to the target, only an "enemy" of the target. This can be handy in a 3-way fight (berserking monsters, released prisoners, Gated fiends, etc) or with dominated enemies compelled to fight against their former allies.
You can safely move through an enemy's space if it is two sizes larger or smaller than you, treating it as difficult terrain. ie Halflings can move through a Dire Wolf's space but not a Rat's, and vice versa for Humans.
Your damage will spike upwards if you manage to get reaction attacks with Sneak Attack. See "Ways to attack with your Reaction" in the Handy links section.
Have your allies force monster movement with Turn Undead, Dissonant Whispers, Confusion, etc to trigger Opportunity Attacks. Pushes and pulls don't work.
An owl familiar, yours or not, can do a flyby Help action to set up Sneak Attack.
Thieves: Use healing kits in conjunction with your Fast Hands feature and the Healer feat to heal 1d6+4+level as a bonus action.
Assassins: Hidden intentions and sudden betrayal can be just as surprising as a hidden position and sudden ambush. Et tu, Brute?
Arcane Tricksters: You can see through your own, and possibly your allies', illusions. Use this to establish Sneak Attack conditions from behind or even inside an illusion.

Gaining Advantage

Hide
Attacking while hidden from your target, ie with a successful stealth check
Attacking while unseen from your target, ie while invisible or behind/within Total Cover or a Heavily Obscured area
Target is blinded, paralyzed, petrified, prone (within 5'), restrained, stunned, unconscious
Target is under the effect of Faerie Fire, Guiding Bolt, Otto's Irresistible Dance
Target is squeezing through a space one size smaller than itself
You are under the effect of Foresight, True Strike
You have inspiration from your DM
You have the Assassinate or Versatile Trickster class feature
Ally uses the Help action on your target

Attacking from long range with a ranged weapon
Attacking with a ranged weapon within 5' of an enemy
Attacking while underwater without a swim speed, except with a dagger or shortsword
Target uses the Dodge action (and you are visible)
Target is unseen, ie invisible, etc.
Target is prone (>5' away)
Target is under the effect of Blur, Foresight, Holy Aura
You are blinded, poisoned, prone, restrained
You are under the effect of Otto's Irresistible Dance,
You are wearing armor/shields you are not proficient in
You are under the effect of level 3 exhaustion
You are encumbered
You are squeezing through a space one size smaller than yourself
You have been raised with Resurrection after being dead for more than a year
Remember that it only takes one source of advantage or disadvantage to cancel both out, no matter how many sources of each there are.

 

[clutchbone]

Hi Zardnaar. Thank you for saving my guide. Would you kindly credit me with authorship of the content? Alternatively I can just repost it.

 

[Morrus]

Hi Zardnaar. Thank you for saving my guide. Would you kindly credit me with authorship of the content? Alternatively I can just repost it.

I can transfer ownership of the posts to you if you like? Seems the most expedient way!