Posted in: Dungeons and Dragons 5e

Mastermind Rogue Guide [D&D 5e]

Last Updated on October 15, 2023

In the dynamic world of Dungeons and Dragons 5th Edition (D&D 5e), the role you play in your adventuring party can make or break your gaming experience. In this comprehensive guide, we delve into the Mastermind Rogue, a rogue subclass designed for players who enjoy secrets, espionage, and intrigue. We’ll discuss its strengths, weaknesses, key features, and the best ways to optimize your character. So, if you’re eager to master the art of being a rogue with a twist, read on and discover the ins and outs of the Mastermind Rogue in D&D 5e.

Role in the Party

The Mastermind Rogue is a social form of rogue centered around secrets, spying, and intrigue. Unfortunately, it’s considered one of the weaker rogue subclasses, mainly due to a feature redundancy issue introduced in Tasha’s Cauldron of Everything. While it had potential, this subclass now lags behind other rogue choices. However, that doesn’t mean it’s entirely devoid of merit.

As a Mastermind Rogue, you’ll still engage in typical rogue activities like sneaking and stabbing, but you’ll bring something extra to the table – the power of friendship, which can be a valuable asset to your allies.

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Mastermind Rogue Features

Master of Intrigue

At 3rd level, you gain proficiency with the disguise kit, forgery kit, and one gaming set of your choice. Additionally, you learn two languages of your choice. You can also mimic speech patterns and accents of creatures you’ve heard for at at least 1 minute. This allows you to pass yourself off as a native speaker of a particular land, provided you know the language.

While initially viewed as a ribbon feature, the three tool proficiencies, two languages, and the ability to mimic accents make it more valuable in campaigns where disguises and forgeries play a significant role.

Master of Tactics

Starting at 3rd level, you can use the Help action as a bonus action. Furthermore, when you use the Help action to aid an ally in attacking a creature, the target of that attack can be within 30 feet of you, rather than the typical 5 feet, provided they can see or hear you.

This feature lets you grant advantage to your allies, making it quite useful in combat situations. However, it competes with the Cunning Action feature for your bonus action and may not always be the optimal choice.

Insightful Manipulator

When you reach 9th level, you can assess a creature’s capabilities outside of combat after spending at least 1 minute observing or interacting with them. You can determine whether the creature is your equal, superior, or inferior in terms of Intelligence, Wisdom, Charisma scores, and class levels.

While this feature sounds intriguing, its practicality is often limited as you can usually deduce such information from context clues.


Beginning at 13th level, you can divert an attack meant for you to target a creature within 5 feet of you providing you with cover. This ability has limited practicality, as the usage of creatures as cover is often inconsistent in D&D.

Soul of Deceit

At 17th level, your thoughts become immune to telepathic reading, and you can present false thoughts through a Charisma (Deception) check. However, the usefulness of this feature is debatable, as enemies can often obtain information through alternative means.


The Mastermind Rogue shines at 3rd level, offering valuable utility with extra proficiencies and the ability to grant advantage to your party members. This bonus action Help action can be a game-changer, especially when aiding other high-damage party members.


Despite its initial strengths, the Mastermind Rogue lacks significant features beyond level 3. You still suffer from typical rogue weaknesses, such as lower hit points, a lower armor class, and limited damage output at higher levels.

Best Race Options

If you want to specialize in deception, the Changeling race is an excellent choice, as it allows you to instantly change your appearance. Githzerai also offer advantages with their Detect Thoughts ability, a boon for any social character. Halflings, specifically Lightfoot halflings, can help you remain stealthy and redirect attacks towards bigger allies.

Choosing the Right Skills

Perception and Stealth are vital skills for rogues. Sleight of Hand is essential for theft, while Acrobatics and Athletics can aid in various physical challenges. Additionally, a socially-focused rogue should consider proficiency in Insight, Persuasion, and Deception.

Fitting Feats

Consider the Ritual Caster feat to add magical rituals to your toolkit or Elven Accuracy if you’re an elf, which can improve your accuracy. Eldritch Adept can give you useful warlock invocations.

Optimal Backgrounds

For a rogue focused on deception, the Charlatan background is suitable, although it leans more towards an evil character. The Criminal background is a classic choice for rogues, offering opportunities for sneaky activities. The Courtier background is ideal for a rogue raised in a noble family.

Multiclassing Options

Multiclassing can open up intriguing possibilities for your Mastermind Rogue. You might consider starting as a Hexblade Warlock at level 1 to leverage charisma for attacks and access various benefits. Alternatively, a Barbarian multiclass can turn you into a robust strength-based rogue. A one-level dip in Wizard can also bring some powerful spellcasting abilities to your repertoire.

Would I Recommend Playing a Mastermind Rogue?

In a low to mid-level campaign, the Mastermind Rogue can offer a satisfying experience, especially if you value the bonus action Help action. However, it’s important to note that this subclass doesn’t offer much beyond level 3. If you’re unsure about the utility of the high-level features or prefer a rogue subclass with more consistent benefits, you may want to explore other options. For those who seek a unique twist, the Barbarian multiclass offers an unconventional and entertaining approach to this subclass.

In the dynamic world of Dungeons and Dragons 5th Edition, the Mastermind Rogue might be your path to intrigue and subterfuge. Whether you choose to follow this rogue’s path or explore others, the world of D&D is vast and filled with endless possibilities. Your journey awaits – make it a memorable one!

Advancing Your Mastermind Rogue

As you progress through the levels as a Mastermind Rogue, it’s essential to consider how to optimize your character and make the most of your unique abilities. Let’s explore some strategies and tips for advancing your character effectively:


While the Mastermind Rogue is unique in its own right, multiclassing can provide exciting opportunities to diversify your skillset. Here are a few potential multiclassing options to consider:

1. Bard: Multiclassing into Bard can enhance your social abilities and provide you with spellcasting, which can be valuable for utility and control. The College of Lore is particularly fitting for a character focused on knowledge and subterfuge.

2. Fighter: A few levels in Fighter can grant you the Action Surge ability, increasing your combat effectiveness. Consider the Battle Master archetype for additional combat maneuvers.

3. Warlock: If you’re looking to amplify your magical capabilities, a multiclass into Warlock can be beneficial. Pact of the Chain can provide you with a valuable familiar, while the Archfey patron can enhance your enchantment spells.

4. Wizard: As a Wizard multiclass, you gain access to a broad range of spells and arcane abilities. Consider the School of Enchantment for a thematic fit with your Mastermind Rogue.

Magic Items

As a Mastermind Rogue, you can greatly benefit from specific magic items that complement your abilities. Some valuable magic items to consider include:

1. Cloak of Elvenkind: This cloak grants advantage on Dexterity (Stealth) checks, making you even more elusive.

2. Hat of Disguise: Enhance your role-playing and infiltration abilities with the ability to change your appearance at will.

3. Bracers of Archery: If you use ranged weapons, these bracers grant a +2 bonus to damage rolls with bows and crossbows.

4. Ring of Mind Shielding: Given your focus on secrets and subterfuge, this item can protect your thoughts from prying magical effects.

Roleplay and Creative Problem Solving

Remember that the Mastermind Rogue excels in the realm of roleplay and creative problem-solving. Your unique abilities, such as mimicry and the ability to assess an opponent’s strengths and weaknesses, provide ample opportunities for intriguing interactions and plot developments.

Consider how your character’s past, motivations, and personal connections can add depth to your roleplaying. Forge alliances, manipulate situations, and use your cunning to outsmart your adversaries.


The Mastermind Rogue in D&D 5e is a captivating choice for players who relish the art of subterfuge and intrigue. While it may have its shortcomings, the right player can make this subclass shine in the right campaign. Embrace the power of friendship, deceive your foes, and use your skills to become the ultimate puppet master in the world of D&D.

As you continue your journey as a Mastermind Rogue, always remember that your choices, creativity, and clever tactics can transform a seemingly weaker subclass into a formidable force at the gaming table. Whether you’re a master of manipulation or a cunning trickster, the possibilities are endless in the ever-evolving world of Dungeons and Dragons 5th Edition.

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