D&D 5E Basic Build Series: Rogue

Author: SmugLookingBarrel

The Rogue offers an alternative approach to a weapon-using playstyle. Its unique method of dealing damage, with a single strong hit boosted by Sneak Attack, gives the Rogue that extra flair if you enjoy seeing many dice and big numbers, in contrast to other martials who rely on Extra Attack. The extra skill proficiencies and Expertise of the Rogue offer non-magical out-of-combat utility. If you don’t enjoy managing resources whatsoever (other than hit points), the Rogue is a good contender for your class choice. This build, part of our Basic Build Series, uses the Phantom roguish archetype to add extra damage from Wails of the Grave and to access the solid defense and utility from Ghost Walk.

Race: Human (Variant)

Ability Score Increases – +1 Dex, +1 Con.
Feat – Crossbow Expert. This will give us an additional attack on our turn, which in addition to increasing our damage in general, gives us a second opportunity to hit and apply our Sneak Attack. Getting to shoot in melee without disadvantage is significant as well, since disadvantage disqualifies us from being able to use our Sneak Attack.
Skill – Perception. The most used skill in the game, important for every character. 
Languages – Common and Dwarvish. The language choice doesn’t really matter, as it is campaign dependent and should be discussed with the DM. It can be useful to speak different languages from the rest of the party, or to have one obscure non-Common language that the entire party shares, so you can converse without the NPCs knowing what you’re talking about. 

Class: Rogue

Skills – Acrobatics, Insight, Sleight of Hand, Stealth. Acrobatics is an important skill to be able to resist a grapple, Sleight of Hand and Stealth are staple Rogue skills that you’ll be good at. Insight is another useful skill, made better since we’ll have a solid Wisdom score.  
Expertise – Perception, Stealth. Perception is very important, so getting this bonus will help a lot with noticing hidden enemies, and Stealth is useful to hide yourself. 
Sneak Attack – Once per turn when we hit with an attack with a finesse or ranged weapon, we can deal 1d6 damage, scaling based on Rogue level. This ability forms the basis of the Rogue’s damage, and being able to make proper use of it is what separates optimized rogues from normal rogues. 

Ability Scores

8 Str, 15+1 Dex, 15+1 Con, 10 Int, 14 Wis, 8 Cha

Dexterity governs our weapon attacks and AC, so we’re starting with a 16 after racial bonuses. Constitution is important to any character, and since we can afford it, we’re taking a 16. We’ll take 14 Wisdom to boost our Perception and one of the most important saving throws, then we have 2 points left so we’ll put them into Intelligence. 

Background (Noble)

This build needs a lot of expensive equipment right at level 1, so we’re choosing the Noble background because it has the most starting gold of any background. 

Skills – History, Persuasion. Two skills that are reasonably useful. 
Tools – Dragonchess set.
Feature – Position of Privilege. This can be a very useful feature, in a lot of circumstances you’re dealing with commoner NPCs, and having a feature like this can offer some good roleplaying benefits. 
Creator’s Note – Making a custom background is RAW, the PHB on page 125 states, “The sample backgrounds in this chapter provide both concrete benefits (features, proficiencies, and languages) and roleplaying suggestions…To customize a background, you can replace one feature with any other one, choose any two skills, and choose a total of two tool proficiencies or languages from the sample backgrounds.” For the sake of simplicity, the Noble background was chosen here, but feel free to create a background that suits your character.

Equipment

Rogue Starting Equipment 

• Rapier (25 gp)
• Shortbow and quiver of arrows (25 gp)
• Explorer’s pack (10 gp)
• Leather armor (10 gp)
• Two daggers (4 gp total)
• Thieves’ tools (25 gp)

Noble Background Starting Equipment

• Set of fine clothes
• Signet ring
• Scroll of pedigree
• 25 Gold

Purchasing Goals

• Our primary weapon, the hand crossbow, is something that a Rogue can’t start with, so our absolute top priority is getting one. The equipment we start with has its worth displayed because if you can sell everything you own and buy a hand crossbow, you should. A lot of DMs allow you to do this before you start, but if not you should dual wield shortswords until you can. Don’t forget the bolts!
• Studded leather armor, for the extra Armor Class.
• Though you can’t usually choose magic items you can access, a magic hand crossbow, to bypass monsters’ damage resistance would be invaluable for the build. 

Level 1 Strategy

At level 1, we’ll be attacking twice with our shortswords (or hand crossbow, if we have one) while hopefully applying Sneak Attack, which leads to this build having the highest damage of any character at level 1. The 1d6 extra damage, which we have two chances to activate, is better than any other class features at level 1. It’s also completely resource-independant; we can do it infinitely.  We don’t have the best defense, so ideally we don’t want to stay in melee with multiple enemies, but we can often drop an enemy full health to death on our turn.

Why pick Crossbow Expert when you will have Cunning Action?

Although Cunning Action is a good ability on its own, you don’t always need it, and it won’t always work. Rogue suffers from having only one attack, and it will fail to catch up with other martials if they pick up abilities that improve their attacks. When the condition for sneak attack is met, attacking twice is always better than once with advantage from Hiding, even before considering advantage from other sources, and when you’re using your Cunning Action to Hide, you’re incorporating a second ability check into the mix, using your Stealth skill. While you’ll eventually be able to get your Stealth modifier high enough to virtually guarantee success, that doesn’t come until much later, and until then, relying on Cunning Action means making another roll to have advantage on your attack roll. Steady Aim, from Tasha’s Cauldron of Everything, is similar but has a different problem: It renders you immobile, and being immobile is a major detriment for a character without the defenses to tank. 

Level 2 Rogue

Cunning Action – We can use a bonus action on our turn to Dash, Disengage, or Hide. 

Level 2 Strategy

Now that we have both Crossbow Expert and Cunning Action, we have some competition for our bonus action. If we’re directly comparing making two attacks with Crossbow Expert to making one attack at advantage with a Cunning Action hide, then two attacks is strictly superior, but we’re a Rogue, and the fact that Sneak Attack requires advantage complicates this, because making one attack at advantage and applying Sneak Attack is more damage than making two attacks that do not apply Sneak Attack. So, if you’re going to get Sneak Attack already, always make two attacks. If you’re not going to get Sneak Attack already, and you think you have a reasonably chance to get advantage by Hiding, do that instead. 

Level 3 Rogue

Sneak Attack scales to 2d6 at this level, which is a very solid amount of damage given how likely we are to apply it with our two attacks.
Roguish Archetype – Phantom. 
Whispers of the Dead (Phantom feature) – We can now choose a new skill or tool proficiency every short rest. This can be very helpful in situations where we know what specific kind of skill challenge awaits us in the next encounter (or adventuring day). A boon to our versatility.
Wails of the Grave (Phantom feature) – After a Sneak Attack, we can deal half our Sneak Attack damage to a second target, and we can do this a number of times equal to our proficiency. At this level, getting 1d6 damage twice per long rest isn’t great, but this scales very well, both increasing in damage and getting more uses as we level. The damage is also completely unavoidable, no save and no attack roll, which is nice. 
Steady Aim (Tasha’s Cauldron of Everything Optional feature) – We can use a bonus action to grant ourselves advantage on our next attack, at the cost of giving up our movement. This is worth using if you can’t get an ally in place to provide Sneak Attack. 

Level 3 Strategy

Now that we have Steady Aim, our options for attack don’t change significantly, we can either make two attacks or one attack with advantage, the difference being that we can now guarantee advantage with our bonus action at the cost of our movement. So, you should again make two attacks if you have Sneak Attack from another source, otherwise use Steady Aim, unless the inability to move is a significant issue, in which case you should use Cunning Action to Hide. 

Level 4 Rogue

Ability Score Improvement (Feat) – Sharpshooter. While this feat is normally taken for the ability to gain +10 damage at the cost of -5 to hit, we will not be using this part of the feat all the time. We’re mostly interested in the range increase we get from being able to shoot at long range without disadvantage, which increases our effective range from 30 to 90. Being able to ignore cover is also a solid bonus.

Level 4 Strategy

Now that we have Sharpshooter, our options for attack actually become much more complicated: In addition to the comparison of two attacks or one with advantage, we can use Sharpshooter on any attack, or not. The original, first order strategy stays the same: it’s always better to make two attacks rather than one with advantage, unless you wouldn’t have Sneak Attack. However, now the decision tree splits further!

Presented below is a graph of the most optimal tactic at each level for each AC value of the target. Assuming you have Sneak Attack from another source, that tactic will always be one of:

• Make both attacks without Sharpshooter.
• Make both attacks with Sharpshooter.
• Make your first attack with Sharpshooter, then if the first attack hits, use Sharpshooter again, and if not, attack normally. 
• Make your first attack without Sharpshooter, then if it hits, use Sharpshooter, if not, attack normally.

The X-axis for this graph is AC for the enemy you are attacking. The Y-axis is your character’s level. This accounts for Ability Score Improvements, feats, proficiency bonus increases, and Sneak Attack damage scaling.

Here at level 4, we can see that:

• If you think an enemy has 14 AC or less, you should use Sharpshooter’s -5/+10 on both of your attacks. Using Sharpshooter on both attacks against a target with poor AC remains an effective tactic for the rest of your career.
• At exactly 15 AC, the most damage per round is achieved by using -5/+10 on the first attack, but only on the second attack if the first attack hits. This strategy becomes better later on, eventually becoming the “default” heuristic for normal AC values as our Sneak Attack dice grow in proportion to Sharpshooter’s damage.
• At 16 and 17 AC, the strategy for optimal damage inverts. Do not use -5/+10 on either attack, unless the first attack hits. This strategy stays niche for “medium-high-ish” AC values.
• Between 18 AC and 23 AC, you shouldn’t use -5/+10 at all, as the extra damage you deal isn’t worth the significantly increased chance of losing all your damage on a miss. The number of situations where this is the best tactic decreases as you gain levels, since your ability to hit enemies scales faster than the monster’s AC for extremely high values. The highest monster AC currently in the game is 25, which won’t be nearly as hard to hit at level 20 as an 18 AC monster is to hit at level 4.
• If for some reason you are fighting an enemy with AC so high that you need to roll a 20 to hit anyways, you might as well use Sharpshooter on every attack, since it won’t affect your chance to hit.

Thank you to Tabletop Builds contributor Esker for writing the R script to create the graph above. The math to develop the optimal strategy for this (or a similar) build might very well be an entire article itself.

Refer to the chart above for optimal decision-making as the build progresses. Remember the graph only comes into play if you do not need to use your bonus action to enable Sneak Attack.

Graph TL;DR

Low AC	Sharpshooter twice
Medium AC	Sharpshooter the first attack, and if it hits, Sharpshooter the second
High AC	Normal attack the first attack, and if it hits, Sharpshooter the second
Very High AC	Normal attack twice
Need a Critical Hit	Sharpshooter twice

What if I don’t know the enemy’s AC?

All of this math is assuming the enemy’s AC is known, which in practice, sometimes it is, sometimes it’s not. Being able to approximate what your target’s AC might be is an important skill for anyone using Sharpshooter. Here are some tips that might help in that regard. 

1. When combat begins, ask your DM about the enemy. Ask if they appear to have a tough hide or heavy armor. It’s generally best not to use the words “Armor Class” directly, but you can often gain valuable information from a general inquiry into the target’s apparent capabilities. 
2. Keep track of which attack rolls hit and miss. If one of your allies rolls a 15 and misses, then your next ally rolls a 16 and hits, you now know your target’s Armor Class exactly, barring special circumstances. 
3. Note any case where the DM tells a party member they’ve just barely missed. Some DMs will make special mention if a player’s attack misses the monster by just 1 or 2, and any case of this can be very helpful when attempting to know the enemy’s AC.

This is way too confusing, is there a more basic Basic Rogue I should play?

Rogue is often touted as being a simple class to play, with few decisions to make, so this complexity might be off-putting for some. If you’d rather play a build in which your plan of attack is the same on every turn, consider this short alternate version of the build:

Take Wood Elf instead of Variant Human, begin with an ability score array of 8 Str/15+2 Dex/15+1 Con/10 Int/14 Wis/8 Cha. For your Ability Score Improvements, choose Elven Accuracy (+1 Dex), +2 Dexterity, Sharpshooter, Fighting Initiate (Archery), Resilient (Constitution), Lucky. This build deals comparable damage to the build in this guide while also being much simpler to play. If not for the requirement that Basic Builds use Variant Human, this would be the build we suggested. Your plan of attack is to always use either Hide or Steady Aim, then make one attack with advantage and Elven Accuracy. Always use Sharpshooter once you get it.

Level 5 Rogue

Sneak Attack scales to 3d6 at this level, which is a reasonable amount of damage, especially since we’ll be very likely to apply it, but it’s less dramatic of an increase than we would expect to see at level 5.
Uncanny Dodge – When we’re hit by an attack, we can halve the damage with our reaction. Decent protection at this level, but being a reaction defense against one attack means it will be less useful as we advance.

Level 6 Rogue

Expertise – Acrobatics, thieves’ tools. We get our second round of Expertise here, and we’re taking Acrobatics to keep us from being grappled and thieves’ tools to help us disarm traps. 

Level 7 Rogue

Sneak Attack scales to 4d6.
Evasion – If we’re subjected to an effect that allows a Dexterity save for half damage, we take no damage if we succeed, and half damage if we fail. A solid defensive feature that protects us against some nasty damage effects like fireball spells and many kinds of dragon breath, and given our low hit points, any feature that allows us to avoid damage is good. 

Level 8 Rogue

Ability Score Improvement (Feat) – Fighting Initiate (Archery). We really want to be hitting with our attacks, so getting the +2 to hit from Archery style is more significant to us than the +1 to hit and +1 to damage we would get from raising our Dexterity. 

Level 9 Rogue

Sneak Attack scales to 5d6.
Tokens of the Departed (Phantom Feature) – As a reaction when a nearby creature dies, we can get a soul trinket, and use it either for a free Wails of the Grave, or to ask it a question. We also have advantage on death and Constitution saving throws while we have a trinket, and can hold a number of trinkets equal to our proficiency bonus. Ideally, you should never be holding more than one of these and should be continuously using them as you acquire them to get more damage from Wails of the Grave, though it can be useful to keep one trinket on you for the advantage on Constitution saves. The utility of asking a question is totally up to the DM but it’s worth a shot if you need information. 

Level 10 Rogue

Ability Score Improvement – +2 Dex. Now that we have the important feats we need, we’ll be raising our Dexterity for our next two Ability Score Improvements, which boosts our attacks, our AC, our initiative, and our skills. 

Level 11 Rogue

Sneak Attack scales to 6d6.
Reliable Talent – Whenever we make a proficient skill check we can’t roll lower than a 10. Since we have a proficiency bonus of +4 at this point and high Dexterity, this will nearly guarantee success for any of our proficient skills. 

Level 12 Rogue

Ability Score Improvement – +2 Dex. We now have 20 Dexterity and thus the maximum bonus to our attacks, our AC, our initiative, and our skills. 

Level 13 Rogue

Sneak Attack scales to 7d6.
Ghost Walk (Phantom feature) – As a bonus action and lasting for 10 minutes, we get a flying speed of 10 feet, disadvantage on all attack rolls against us, and we can phase through solid objects, taking 1d10 force damage if we end our turn inside an object. We get one use for free and can use it again with a soul trinket. Ideally we want this to be up in every combat, as most monsters deal much more than 1d10 damage per turn, but can’t hit you at all if you’re inside a wall or the ground. In situations where your ability to hide won’t help you avoid damage, this hopefully will. 

Level 14 Rogue

Blindsense – We’re now aware of the location of any creature within 10 feet of us that’s hidden (the feature also specifies invisible, but according to Rules as Written, you’re already aware of the location of invisible creatures that are not hidden). It’s situational, but good if it comes up. 

Level 15 Rogue

Sneak Attack scales to 8d6.
Slippery Mind – This comes in late, but proficiency in Wisdom saves is nice, as those are often debilitating to fail. 

Level 16 Rogue

Ability Score Improvement (Feat) – Resilient (Con). Now that we have our Primary Ability Score capped, and the offensive feats we need, we’ll be grabbing proficiency in Constitution saving throws to help us out defensively. Many debilitating or deadly effects use Constitution saves, so gaining proficiency in them will help keep us alive. We now have proficiency in all three of the most common saving throws.

Level 17 Rogue

Sneak Attack scales to 9d6.
Death’s Friend (Phantom feature) – When we use Wails of the Grave, the initial target takes the same necrotic damage, which is great. This is essentially 4d6 damage added to our Sneak Attack. We also get one free soul trinket per long rest, which is minor but not nothing, letting us use our Ghost Form to scout while still having it up for combat. 

Level 18 Rogue 

Elusive – Attack rolls can’t have advantage against us unless we’re incapacitated. While being attacked with advantage isn’t that common, this is still solid when it comes up. If your DM rolls behind a screen, remember to let them know you have this. 

Level 19 Rogue

Sneak Attack scales to 10d6.
Ability Score Improvement (Feat) – Lucky. Three times per day, we can reroll any d20 we roll, or a creature’s attack against us. Your best use for these is to save these for important attacks that you miss, or if an enemy hits you with a critical hit.

Level 20 Rogue

Stroke of Luck – Once per short rest, we can turn a miss into a hit, or turn a failed check into a natural 20. It’s quite limited in uses, but being able to guarantee an outcome for anything is a luxury in D&D, so you’ll be happy to have this capstone.