Mastermind Rogue Build Guide – The Lord of the Lies – 2024 Update
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For all D&D guides on Nat1gaming, they only use the main sourcebooks (Player’s Handbook, Tasha’s Cauldron of Everything, Xanathar’s Guide to Everything) as well as Strixhaven: A Curriculum of Chaos (mostly for Silvery Barbs) as those tend to be the most commonly used books at tables. Always be sure that if you’re following a guide that you’re adhering to your tables rules about what sourcebooks you are allowed to follow.
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For the purposes of this guide, it will be assumed that you would not be multiclassing. While multiclassing can be excellent for many of these, this is for those who want to play the build all the way through in the same class. Guides that use multiclassing will be separate from these.
For spellcasters, you may notice substantial overlap between the spell lists of builds with the same base class. This is due to each guide utilizing a generically good spell list and not considering extenuating factors that will influence how you particularly sculpt your spell list. When creating your own spell list, you should take into account the campaign setting, what spells any other party members are capable of casting, potential overlap (ritual spells tend to overlap so it’s rare you need multiple people capable of casting them), or potential shortcomings in the parties total spell list. While this guide can definitely help point you in the right direction for crafting a spell list, you should use your judgement and preferences to figure out what spells make the most sense for your character.
To that end, please refer to the Spell List and Spell Tier list for any substitutions you’d want to make to the build.
Why Mastermind Rogue?
While this class has functionally no combat skills, you have a plethora of out of combat abilities that you can utilize to problem solve from a really different angle. That said, the abilities are very specific and not that strong which is disappointing, but if you’re willing to amend the power level of some of the abilities, this can be a really interesting and fun class to play that prioritizes out of combat answers versus always bonking enemies.
Mastermind Rogue Abilities Ranked
Master of Intrigue (Level 3) – B- Tier – This is a lot of proficiencies packed into one skill, and if you’re picking this class, I would assume you can make them useful.
Master of Tactics (Level 3) – C Tier – This is a really interesting feature, and while it’s hard to say if you’d prefer to do this or a different Cunning Action, this ability is good enough to at least consider using it over your Cunning Action.
Insightful Manipulator (Level 9) – D- Tier – There are similar features to this that are so much better, and while this isn’t useless, it’s close.
Misdirection (Level 13) – D- Tier – While this is actually a strong ability, the amount of set up required to fully capitalize on this is ridiculous. This would only work if an enemy is covering you from another enemy attacking at ranged, and even then, they can probably establish another sight line instead. I will say though that there is a lot of comedic value to using this on your allies assuming your table is close enough friends where this would be funny rather than infuriating. That said, even if you could use this tactically with allies (hide behind your tank), enemies could still just move in such a way to not trigger this pretty easily.
Soul of Deceit (Level 17) – D- Tier – This should’ve been a third level ability, and even if it were, it would get this rating. This is so unbelievably niche that I’m surprised this was approved to be the capstone.
Quick Level Up Guide
| Level | Class Features/Feat | Notes |
| 1 | Expertise, Sneak Attack, Thieves’ Cant, Weapon Mastery | Sneak Attack 1d6 |
| 2 | Cunning Action | None |
| 3 | Mastermind Master of Intrigue Master of Tactics Steady Aim | Sneak Attack to 2d6 |
| 4 | Feat: Skulker (DEX) | None |
| 5 | Cunning Strike, Uncanny Dodge | Sneak Attack to 3d6 |
| 6 | Expertise | None |
| 7 | Evasion, Reliable Talent | Sneak Attack to 4d6 |
| 8 | Feat: Crossbow Expert (DEX) | None |
| 9 | Insightful Manipulator | Sneak Attack to 5d6 |
| 10 | Feat: Mage Slayer (DEX) | None |
| 11 | Improved Cunning Strike | Sneak Attack to 6d6 |
| 12 | Feat: Constitution to 18 | None |
| 13 | Misdirection | Sneak Attack to 7d6 |
| 14 | Devious Strikes | None |
| 15 | Slippery Mind | Sneak Attack to 8d6 |
| 16 | Feat: Constitution to 20 | None |
| 17 | Soul of Deceit | Sneak Attack to 9d6 |
| 18 | Elusive | None |
| 19 | Epic Boon: Boon of Combat Prowess | Sneak Attack to 10d6 |
| 20 | Stroke of Luck | None |
Level One Build
Species: Halfling
Attributes:
| POINT BUY | |
| STRENGTH | 8 |
| DEXTERITY | 15 (+2 background) = 17 |
| CONSTITUTION | 15 (+1 background) = 16 |
| INTELLIGENCE | 8 |
| WISDOM | 14 |
| CHARISMA | 10 |
Class: Rogue
Class Features: Expertise, Sneak Attack, Thieves’ Cant, Weapon Mastery
Skill Proficiencies: Acrobatics, Insight, Investigation, and Perception
Background: Criminal (Alert)
Starting Equipment: Scimitar, Dagger, Shortbow and quiver of 20 arrows, Leather Armor, Thieves’ Tools, and 11 gp + 50 gp from background
Species: Halfling
While I’m not a big fan of what Halfling brings to the table, being able to Hide behind a larger party member is really good if you miss with your Vex weapon and don’t have any other form of obscurement in combat. That said, the other abilities are decent as well, even if they won’t be relevant that often.
Attributes
| POINT BUY | |
| STRENGTH | 8 |
| DEXTERITY | 15 (+2 background) = 17 |
| CONSTITUTION | 15 (+1 background) = 16 |
| INTELLIGENCE | 8 |
| WISDOM | 14 |
| CHARISMA | 10 |
Dexterity and Constitution are always going to be the Rogue’s primary stats, and your extra points can go to either pumping Wisdom or Charisma depending if you want better saving throws or better conversation skills.
Proficiencies: Acrobatics, Insight, Investigation, and Perception
Common proficiencies for Rogue as between these and your background you have all the DEX skills covered as well as other great proficiencies.
Background: Criminal
Good proficiencies, great feat, and it makes a lot of sense with Rogue in general
Starting Equipment – Scimitar, Dagger, Shortbow and quiver of 20 arrows, Leather Armor, Thieves’ Tools, and 11 gp + 50 gp from background
This is very similar to the starting equipment, but the Scimitar is much better than the Shortsword so you have to take the starting gold to get it.
Class – Rogue
Rogues are a very versatile class with a lot of practical applications in and out of combat making them a fan favorite. Starting off, Rogues come with three abilities: Expertise, Sneak Attack, Thieves’ Cant, and Weapon Mastery.
Expertise allows you to take two of your skills and add double your proficiency bonus to them to make them extremely reliable. While the skills you select really depends on what you personally prioritize, it’s hard to go wrong with Perception and Stealth. These are two excellent skills you are going to constantly use so making them as consistent as possible will constantly pay off.
The second ability is the Rogue’s most iconic one – Sneak Attack. Sneak Attack adds extra damage if you can attack an enemy while you have advantage from any means. Normally, this is going to mean you’re hiding, beat the enemies Perception check, and you’ll have advantage on that attack and can Sneak Attack. Every two levels you add an additional d6 to the damage you deal which is pretty solid scaling, although it will generally not keep up compared to other martial classes.
The third ability, which is really just pure flavor, is Thieves’ Cant. This is like its own language that only other rogues or similarly nefarious individuals would know so you can speak in code and such.
The final ability is Weapon Mastery, and you should take the Scimitar and Shortbow mastery considering that’s what you’re going to be using! As a note, make sure your Scimitar is in your main hand to make use of its Weapon Mastery property effectively.
The Build Level 2 Onward
Level 2-5
Level 2
Class Features: Cunning Action
One of the best abilities on Rogue, you can now convert your Bonus Action into a Dash, Disengage, or the Hide action. While the Hide Action is going to be the most common action taken so you can continuously get Sneak Attacks, Dash and Disengage are also excellent actions to take if you really need to get out of wherever situation you’re in.
Level 3
Class: Mastermind
Class Features: Master of Intrigue, Master of Tactics, Steady Aim, Sneak Attack to 2d6
Level 3 brings your subclass, Mastermind, and two new features to the table – Master of Intrigue and Master of Tactics.
Master of Intrigue grants you a lot of new proficiencies including the disguise kit, the forgery kit, a gaming set, and two languages. Furthermore, if you listen to a creature speak for a minute, you can pass yourself off as a native speaker of the language provided you know the language. Obviously, all of this is out of combat utility which has a wide range of applicability depending on the specific adventure, campaign, player creativity, and DM flexibility. Considering how many factors are included, it makes it hard to rate compared to a combat ability, but if you like approaching problems from a non-combat angle, this gives you a lot to work with.
Master of Tactics, on the other hand, is a combat ability! Instead of using your bonus action for Cunning Action, you can provide the help action even from a distance to give allies advantage on their attack. While losing advantage on your next attack by hiding does hurt, this is a solid ability that really lets you be a team player when it makes sense to.
Finally, you get Steady Aim which lets you give up your bonus action and movement for a turn in order to have advantage on your next attack. If you have no way to gain advantage otherwise, this is a really nice way to get it!
Level 4
Feat: Skulker (DEX)
Class Features: None
Level 4 brings your first feat, and Skulker is perfect for Rogues! Getting some amount of Blindsight is nice, but the real prizes here are the advantage to hide in battle and missing with an attack doesn’t reveal you which gives you another chance to get that Sneak Attack! These are some really nice abilities that you’re going to get a lot of mileage out of.
Level 5
Class Features: Cunning Strike, Uncanny Dodge, Sneak Attack to 3d6
Level 5 brings two new features to the table with Cunning Strike and Uncanny Dodge.
Cunning Strike is an interesting ability that lets you trade in Sneak Attack damage dice for a small, but generally good additional effect. You start with three different options for your Cunning Strike – Poison, Trip, or Withdraw.
Poison can be solid, but Constitution saving throws are generally the easiest to save out of.
Trip is definitely solid if you have other martial allies and especially if they’re behind you in the turn order (which they will likely be).
Withdraw lets you reposition without drawing opportunity attacks so you don’t have to use your Cunning Action to disengage.
Overall, this ability is pretty good as you have versatile options that can all be impactful!
Uncanny Dodge lets you use your reaction to halve the damage of one incoming attack. Unfortunately, this is a pretty bad ability as multiattacks are going to become more common making the ability to halve just one of those attacks pretty forgettable. Furthermore, Defensive Duelist is going to be taking your reaction more often than not, but if you know that you have to take some damage on a turn, then this is here for you.
Level 6-10
Level 6
Class Feature: Expertise
You get two more bouts of Expertise to pass around, and once again, it really depends on whatever skills you find yourself using often. In a generic sense, I like picking up Insight and either Investigation (if no INT people in your party) or Sleight of Hand.
Level 7
Class Features: Evasion, Reliable Talent, Sneak Attack to 4d6
Level 7 brings two neat abilities with Evasion and Reliable Talent.
Evasion is a really solid ability that makes any effects that forces Dexterity based saving throws way worse against you as you naturally mitigate half of their effect and potentially the whole effect if you pass the save.
Reliable Talent is a cool ability that makes all rolls for skills you’re proficient in be a minimum of a 10, which means you have a much higher chance of passing skill checks with skills you are proficient in and you’ll very rarely fail checks involving skills you have Expertise in.
Level 8
Feat: Crossbow Expert (DEX)
Class Features: None
Level 8 brings another feat, and while you could go straight to 20 Dexterity for the highest AC, attack rolls, and initiative, I like taking two feats instead. To that end, and I really like grabbing Crossbow Expert.
While I do always enjoy Rogues who are in melee, their low AC makes that game plan a bit of a liability, especially if you don’t have many allies with you on the front lines. It’s much safer for you to hang back with two Hand Crossbows and attack from afar, especially if you only hit on your second attack as that’ll break you out of hiding, and if you were in melee range, the enemy could just wallop you freely. If you want to be a Rogue that stays in melee, you can snag Defensive Duelist (DEX) here instead.
Level 9
Class Features: Insightful Manipulator, Sneak Attack to 5d6
Level 9 brings your next subclass ability with Insightful Manipulator!
Insightful Manipulator lets you study a creature and compare your Intelligence, Wisdom, Charisma, and level to theirs, which unfortunately, is not a good ability. There are similar abilities to this in the Battle Master and Hunter kit, but this just does not give you relevant information. Huge miss here.
Level 10
Feat: Mage Slayer (DEX)
Class Features: None
You get yet another feat this level, and you can finally get 20 DEX with Mage Slayer. Being able to really mess with casters is nice as a martial character, and getting a functional charge of Legendary Resistance? Incredible! A really strong feat that I have most of my martial characters taking.
Level 11-15
Level 11
Class Features: Improved Cunning Strike, Sneak Attack to 6d6
Level 11 brings an improvement to your Cunning Strike! Now you can use two Cunning Strike features simultaneously, and while you still have to pay the associated costs, this is still a pretty solid ability!
Level 12
Feat: Constitution to 18
Class Features: None
More health and better saving throws is never a bad thing, even if you’re probably not getting hit that often!
Level 13
Class Features: Misdirection, Sneak Attack to 7d6
Your next subclass feature is Misdirection!
This ability is so awkwardly worded and so unbelievably niche that it’s frustrating. If you are getting attacked by a creature and another creature is providing you any sort of cover from the attack (so only applicable when someone is attacking from range and someone else is close to you I guess), you can have that attack hit them instead. It is going to be so rare that this scenario comes up and any DM cognizant of this can simply move their enemy to a slightly better line of sight and potentially invalidate this. Unfortunately this feature is a huge miss.
Level 14
Class Features: Devious Strikes
You get your final upgrades to your Cunning Strikes with Devious Strikes!
Like the original Cunning Strikes, you get three more options that have both higher costs and more powerful effects with Daze, Knock Out, and Obscure.
Daze can limit somewhat limit what an enemy does on their turn, but considering not many monsters have uses for their Bonus Action, this probably isn’t that good of a feature.
Knockout takes out most of your Sneak Attack dice, but you have a chance to render an enemy unconscious until it passes the save or takes damage. This ability could have been strong if they were stunned for a full turn cycle, but just one ally being able to take advantage of this makes this pretty bad.
Obscure is easily the best of these options as you can potentially blind an enemy which is a pretty brutal status condition.
Overall, this ability is not particularly great, but they can’t all be winners.
Level 15
Class Features: Slippery Mind, Sneak Attack to 8d6
Gaining proficiency in Wisdom and Charisma saving throws is very strong, even if it comes a bit late in your progression. Wisdom, in particular, is the most common spell saving throw you’ll have to contend with so you’ll have a substantially better chance of passing these saves now.
Level 16-20
Level 16
Feat: Constitution to 20
Class Features: None
Max health and CON saves is always great!
Level 17
Class Features: Soul of Deceit, Sneak Attack to 9d6
Level 17 brings your subclass capstone ability – Soul of Deceit!
Your capstone makes you such a good liar you can literally fool magic. This feature is super neat but incredibly niche and disappointing for a final feature. This easily could’ve been a level 3 ability instead and this would’ve been perfectly fine, that’s how weak this is.
Level 18
Class Features: Elusive
As long as you aren’t unconscious, enemies can’t have attacks at advantage against you anymore. This can be good, but it’s not too often that enemies are going to have advantage on attacks against you anyway, so this likely isn’t going to come up often.
Level 19
Epic Boon: Boon of Combat Prowess
Class Features: Sneak Attack to 10d6
Your Epic Boon choice, as I will pick for every martial character, is the Boon of Combat Prowess. Converting a miss into a hit is functionally getting an Extra Attack, but better, and I will take an additional attack every day of the week.
Level 20
Class Feature: Stroke of Luck
Every short or long rest, you can turn any failed d20 test into a critical success. Obviously this is pretty strong, even if you don’t get to use it often.
