At long last, we’re returning to the Dungeons&Dragons Fifth Edition class tutorials! As promised in the Fighter tutorial, this next iteration focuses on the second most 5e popular class: the Rogue. This tutorial is meant to give you a good idea of what to expect from the class, determine if any of the Archetypes speak to your desires for your next character, and provide some roleplaying tips for what kind of characters fit the typical Rogue. Please treat the materials in this post as suggestions; I haven’t play-tested all of the Rogue archetypes from 1st-20th level and therefore cannot provide personal accounts for each variant. However, it’s my hope that you can use what’s contained below to craft your unique and equally incredible Rogue!
Why Play a Rogue?
If Fighters are the Swiss Army Knife of 5e, then Rogues are your Guerilla Warfare specialists. With a 1d8 Hit Die and access to Light armor, you’re not going to be charging the battlefield like some of your full-plated companions. What you lack in defense, however, you make up for in offense via the Sneak Attack. This feature, which is activated once per turn when you hit a creature with advantage or within five feet of another creature it considers an enemy, deals additional damage that scales with you as you level. While a 1st level Rogue will deal an additional 1d6 damage, a 20th level Rogue will add 10d6 points of damage each turn if the proper conditions are met. The best part? This damage doubles on critical hits. That’s right; at max level, you have a five-percent chance of rolling 20d6 additional damage whenever you hit an enemy. And if you’re hitting the target with advantage, your probability of dealing that max-damage goodness gets even higher.
NOTE: One additional caveat to Sneak Attack is that you must make the attack with a finesse or ranged weapon. However, since you’ll want to use weapons that allow you to capitalize on your Dexterity for attacks and damage, you probably won’t struggle to meet this requirement.
In addition to Sneak Attack, Rogues also get Cunning Action, which allows you to always use a bonus action to Dash, Disengage, or Hide. On each turn, you can attack (and hopefully injure) an enemy, then immediately move twice your current movement speed, avoid opportunity attacks while you flee, or use nearby obstacles and shadows to re-mask your presence. This feature, along with Uncanny Dodge and Evasion, are how you go toe-to-toe with the toughest foes and still emerge victorious. This class is great for majorly contributing to the battle while forcing the enemy to focus their attention on the characters who can take the pain (Clerics, Fighters, Barbarians, and Paladins mainly).
For the social and exploration sides, Rogue starts out with proficiency in Thieves’ Tools and the Expertise feature. Expertise allows you to double the proficiency modifier to either A) any two starting skills, or B) one starting skill and your Thieves’ Tools. Then, you get to choose two more skills (or one skill and Thieves’ Tools) to gain this Expertise at 6th level.
NOTE: You cannot gain Expertise on the same skill or Thieves’ Tools twice.
As a Rogue, you can open figurative and literal doors with ease. If your Expertise in Persuasion can’t convince the desperate baron to sweeten the quest reward, use your Thieves’ Tools to pry open his chamber door and pluck a gem-studded amulet for your troubles.
I think the better title for this section is Why Aren’t You Playing a Rogue?
Where Do I Start?
No matter your future Archetype, make sure Dexterity is your highest ability score (AS). Not only will this boost your Armor Class (to offset the low bonus provided by Light armor) and Initiative (to ensure you act faster in combat), but it will directly correlate to your hit-percentage and damage dealt with range weapons (hand crossbow, short bows, etc.) and melee weapons with the finesse property. Oh, and many offensive spells in D&D 5e are checked against your Dexterity saving throw, meaning there is almost no reason to not prioritize this stat.
Your second-highest AS will depend greatly on your Archetype. If you plan to go Arcane Trickster, for example, you’ll want a moderately-high Intelligence score to aid your Spell Save DC and Spell Attack bonus. The Inquisitive, meanwhile, uses Wisdom (Insight) checks for many of its class features. Read through your Archetype’s features carefully to know what AS influences them the most. If you’re running a Thief, which primarily uses Dexterity, then choose the AS which affects your favored skills. When all else fails, pick Constitution for a much-needed HP bump.
NOTE: DMs, consider using these variant Initial Ability Score Increase rules to ensure your players don’t feel trapped into playing races which grant starting Dexterity bonuses, or you’ll end up seeing the stereotypical Elf Rogue over and over again.
From here, note your initial hit points (8 + Constitution modifier) and Saving Throw proficiencies (Dexterity and Intelligent), select your skill proficiencies (refer to p. 95 of the Player’s Handbook), and choose your starting equipment. Finally, note the Expertise, Sneak Attack, and Thieves’ Cant features on your character sheet.
Meet the Archetypes
The Rogue Archetypes, available to you at 3rd level, are incredibly diverse both on and off the battlefield, and each one has a distinct flare guaranteed to capture your imagination session after session. For brevity sake, I’ll only provide a brief summery of the options available in the Player’s Handbook (PHB) and Xanathar’s Guide to Everything (XGE). Although XGE can be considered a source book, always consult your DM before selecting an Archetype found in any non-PHB resource.
Arcane Trickster: Enhance your martial prowess with a little arcane magic! Utilizing spells from the Enchantment and Illusion schools you can create even more creative solutions to your problems. With Mage Hand Legerdemain, you can now use this already-nifty spell to pilfer objects and pick locks from a distance. The Archetype’s ultimate feature, Spell Thief, allows you to rip the ability to cast a spell from a target and cast it, temporarily, as if it were your own.
Primary Stats: DEX and INT
Assassin: Become the ultimate murder machine with the Assassinate feature, which grants you automatic advantage (and therefore Sneak Attack) against a creature who hasn’t acted in combat and grants automatic critical hits against surprised enemies. Paired with the ultimate feature Death Strike, which doubles the damage against surprised enemies, and you’ve got the perfect recipe for a one-shot-one-kill wonder.
Primary Stats: DEX and CHA (for Imposter feature)
Inquisitive: Use your Insight like never before with Insightful Fighting, which allows you to use Sneak Attack on creatures for up to 1 minute under (almost) any circumstance if they fail a Deception check against you. The ultimate feature, Eye for Weakness, grants you an additional 3d6 damage on Sneak Attacks made with Insightful Fighting. The other archetype abilities, like Steady Eye, enhance the ways you make Insight, Perception, and Investigation checks.
Primary Stats: DEX and WIS
Mastermind: Wield the power of subterfuge and misdirection to aid your party and pinpoint the enemy’s weaknesses. With Master of Tactics, you can Help an ally as a bonus action from up to 30 feet away, while Master of Intrigue grants you additional tool proficiencies, two extra languages, and the ability to mimic the speech patterns and accents of others. The ultimate feature, Soul of Deceit, prevents your thoughts from being read (even allowing you to present false thoughts!) and tricks lie-detection magic (e.g., Zone of Truth) into thinking you’re always telling the truth. This Archetype is a little underwhelming, but I can see some clever uses of the earlier features in a high-stakes political campaign.
Primary Stats: DEX and CHA.
Scout: As a distant cousin to the Ranger, you’ll focus on mobility both in combat and in the wild. Using the Skirmisher feature, you can move up to half your movement speed (without provoking attacks of opportunity) when an enemy ends their turn next to you. Sudden Strike, the Scout’s ultimate feature, allows you to make an additional attack as a bonus action on your turn, and you can use Sneak Attack again as long as it’s against a creature who hasn’t been hit by your Sneak Attack this turn. Personally, I enjoy the 13th-level Ambush Master feature better, as it gives you advantage on Initiative rolls and makes it so your allies have advantage on attack rolls against the first creature you hit until the start of your next turn.
Primary Stats: DEX and any other
Swashbuckler: The quintessential duelist and dashing scoundrel. You’ll use Fancy Footwork to strike at enemies and make daring escapes, and your Rakish Audacity will let you make Sneak Attacks against enemies as long as no other creatures are within five feet of either combatant. The Archetype’s ultimate feature, Master Duelist, lets you roll advantage on an attack roll you failed. While most advantage rolls must be made at the same time, this feature allows you to wait until you’ve already missed the mark before trying again. This gives me some heavy Captain Jack Sparrow vibes, and I’m all for it!
Primary Stats: DEX and CHA
Thief: The burglar extraordinaire and Rogue gold standard. With Fast Hands, you can now use your Cunning Action to make Sleight of Hand checks, pick a lock, or attempt to use a complex object. Meanwhile, Second-Story Work allows you to ignore the movement speed penalty imposed by climbing! The Thief’s ultimate ability, Thief’s Reflexes, is phenomenal; you take two turns during the first round of combat. The first turn follows normal initiative, while the second turn activates at your initiative minus 10.
Primary Stats: DEX and any other
How Should I Roleplay a Rogue?
While the Player’s Handbook suggests you pick the Criminal background, you don’t always have to find yourself on the wrong side of the law. Pair your Swashbuckler with the Sailor background for a naval captain, or your Mastermind with the Guild Artisan background with for a novice craftsman with the goal of one day running the entire operation.
Playing the tried-and-true “infamous scoundrel” can be loads of fun, too. When going this route, however, you need to fully consider two things. First, why is your law-breaking PC with the party? And second, what is stopping your PC from seeing the party as another “mark?”
Please, talk with your DM prior to rolling out this character if you’re going to be playing the “money is everything” style thief. D&D is a cooperative roleplaying experience, and that means everyone at the table must know full-well what they’re about to experience. The first question is meant to address any potential conflicts your character may have with law-abiding PCs or the Lawful Good Paladin. Sure, it may be funny once or twice if your pick-pocketing catches the attention of the local guards, but at some point it’ll wear thin if this isn’t the campaign for which your other players signed on.
The second question is to prevent money or items (particular Magic Items) from being stolen from other PCs. There are very few moments more deflating in a campaign than having your hard-won Boots of Elvenkind stolen from you in the middle of the night by another PC. Now, that’s not to say you can never do these things; it’s all about consent. If I know from the outset we’re playing a campaign where the Rogue might steal my items or might even get paid by the BBEG to kill me in my sleep, then I can’t be surprised when it happens.
On the other hand, if you bring these ideas to the table and no one else wants to play that way, workshop some ways with your DM to keep the intent of your character without it harming the other PCs. Perhaps your Rogue takes on a Robin Hood code and only steals from those who have been known to oppress the poor. Alternatively, maybe the adventuring party has secured an ironclad contract for your services which allow you to steal as you please, but under tight restrictions.
Conclusion
Rogues are an absolute blast to play and play with. They’re clever, great problem solvers, and can really bring the pain when needed. Some of the Archetypes, like Mastermind and Scout, feel a bit flat compared to some of the other brilliant choices, but do not let my personal opinion dissuade you from creating the character you want to play! And because the Archetypes are so varied, the roleplaying potential of this class is astronomical. But please, consult your DM and adventuring party first before playing a Rogue who will constantly put the group on the wrong side of the law or will steal money/items from the group. These characters can be fun, but only if everyone at the table is having fun too.
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