Clueing For Looks: A Guide to the Inquisitive Rogue

[TakeitVillain]

Clueing for Looks
A Guide to the Inquisitive Rogue
I really want to add a Sherlock image, but I'm new to Giantitp, so we'll settle for this.

“I need to enter my mind palace!” -BBC’s Sherlock

This series of posts will specifically for D&D 5e’s The Inquisitive, a rogue subclass.

This is an optimization guide, despite I’m highly in favor of unusual combos and don’t think optimization is the be-all-and-end-all. Still, optimization is useful when knowing how to play your character. I like to use that color-coding that all optimization guides like to use.

Red. It is unlikely that this will be helpful. Only do so for roleplaying reasons, which I love.
Purple. Limited in scope and situational.
Black. Middle of the road, not particularly good or bad.
Blue. You should at least shoot for this, because it’s pretty good.
Sky Blue. Amazing. Excellent sleuthing starts here.

I’m excited that this is the first optimization guide I’ve written, so feel free to give me feedback!

Part 1- Intro and Basics

If you’re like me, you love Xanathar’s Guide, for all the wonderful subclasses it includes, including Inquisitives and Swashbucklers. The wonderful dashing derring-do’s already have coverage on the web, so let’s look at our inquisitive fellows (Beware of puns).

It’s been very much helpful to look at Jeremy Crawford’s description of the Inquisitive(see D&D Beyond), so what do they do? Like all rogues, they are good at sneaking and stabbing things, but no one is better equipped to really make sure that chest isn’t trapped.

And more.

They will almost certainly find the clues and hints that no one else will, because almost no one can beat the Inquisitive at Perception and Insight (move over Caduceus). Even more so that their features lend itself to almost duplicating spellcasters and other supernatural abilities. WITHOUT MAGIC. I really enjoy that Inquisitives focus more on the mental and psychological aspects of a characters, rather than our combat-focused rogues that go sneak-attack fishing all the time. (Though Inquisitives do that, just not as much).

Still though, why do you want to play The Inquisitive?
Pros:
• You like rogues. And we know why we like them.
• You live for the mystery likes of Sherlock Homes and Agatha Christie, and you want to live it out in your character.
• While the combat monkeys and faces are stumbling or dodging danger, you easily notice it before it happens.
• You can get sneak attack almost as reliably as a swashbuckler, and that’s saying something.
• You love that look on the dm’s face when you easily deduce out the bad guys and watch it fall into place before you.
Cons:
• You might not be the stealthiest or acrobat-iest rogue out there or be expert at picking those locks. Or being a face, since you’ll want to expertise intelligence and wisdom skills.
• Instead of being the annoying rogue that steals everything or repeatedly sneak attack from afar (though you are also doing that), you’ll notice everything, might ruin the dms’ plans, and they’ll hate you for it.
• Inquisitive are definitely more MAD than the other rogues, since you’ll need Dexterity, Intelligence, and Wisdom.

So how good are those tasty features?
• Ear for Deceit. All the other Insight Rogues are jealous, as you get a minor Reliable Talent for it a level 3, which is upgraded by normal Reliable Talent. As written, it does not apply to Insightful Fighting. Even better if your dm likes to do whispers.
• Eye for Detail. I find often than Perception or Investigation during action takes no actions whatsoever, but that depends on the dm.
• Insightful Fighting. This is what makes you shine during combat. A successful Insight check makes it last for a minute, so you don’t have to do it repeatedly and usually use your bonus action for other cool things. A certain feat makes this gold, which is not part of my ranking system.
• Steady Eye. Your mind palace is staring to get scary, as you get advantage on all Perception and Investigation when you’re only moving half speed.
• Unerring Eye. You’re no spellcaster, but this helps when your spellcasters and paladins don’t have the tools. I would think you’re so intelligent by now, you could get more accurate detail than this.
• Eye for Weakness. Well you just got a boost to your Insightful Fighting. Go crazy.

[TakeitVillain]

There will be more parts for this guide later on, such as races, skill, and feats. All goodness.

[Naanomi]

No rogue makes better use of Magic Initiate: Druid to get Magic Stone for a WIS based ranged sneak attack... guidance and Faerie-Fire don’t hurt either

My last attempt at it was:

Wood-Elf Inquisitive Archeologist
8/16/14/12/16/8
Common, Elven, Deep-Speech, Cartographer’s Tools
Perception, History, Survival, Insight, Investigation, Stealth, Acrobatics
Expertise: Perception, Insight; Investigation, Thieves’ Tools
Observant, Elven Accuracy, Magic Initiate, +2 WIS, Dungeon Delver, Skulker

[TakeitVillain]

No rogue makes better use of Magic Initiate: Druid to get Magic Stone for a WIS based ranged sneak attack... guidance and Faerie-Fire don’t hurt either

My last attempt at it was:

Wood-Elf Inquisitive Archeologist
8/16/14/12/16/8
Common, Elven, Deep-Speech, Cartographer’s Tools
Perception, History, Survival, Insight, Investigation, Stealth, Acrobatics
Expertise: Perception, Insight; Investigation, Thieves’ Tools
Observant, Elven Accuracy, Magic Initiate, +2 WIS, Dungeon Delver, Skulker

A nice point! Dex is still important armor-wise, and I personally love the archaeologist background! Been wanting to play one for a while! Also, I haven't posted it yet, but the spell that I have in mind for the Inquisitive is Hex. I'll let you think it over...

[TakeitVillain]

Part 2- Ability Scores and Races

Ability Scores
• Strength: I don’t exactly remember if literary Sherlock was buff at all, but you’re too MAD to make this a priority.
• Dexterity: Absolutely yes, for all your ranged and finesse attacks, your best save, AC, Initiative, and skill checks. Max this as soon as you can.
• Constitution: Depend on your method. If ranged, a 12 or more should suffice. If you are melee you should have at least a 14, but you’re dodgy.
• Intelligence: Quite important for Investigation and other knowledge checks, but surprisingly not as important as…
• Wisdom: You need this, as it powers Insight, Perception, and your powers as an Inquisitive. You should eventually at least have a 16 in this.
• Charisma: Being a sleuthing detective often puts you in social situations, but that’s what faces are for. You’re not a face.

Races

Player’s Handbook
• Hill Dwarf: Nice defensive features, and you gain some WIS.
• Mountain Dwarf: Strength and Medium armor isn’t that helpful.
• High Elf: You get all the nice elf features, INT, and wizard spells. Not bad.
• Wood Elf: Yes yes yes. You now get the WIS, extra speed, more weapons, and a stealth buff.
• Drow: If you’re in the dark a lot this isn’t bad, but sunlight sensitivity sucks, especially since you’re the main perception monkey.
• Lightfoot Halfling: Halflings are awesome in general, and this helps your hiding.
• Stout Halfling: Also awesome since you instead get dwarfy features.
• Human: This helps ease the MADness.
• Variant: I love feats, you all love feats, Inquisitives love feats.
• Dragonborn: Nope.
• Forest Gnome: Yo this is pretty nice. You get a boost to two important stats, and gnome cunning is fitting for your Inquisitive powers.
• Rock Gnome: You get the intelligence, but not the DEX, which is too important to skip over.
• Half-Elf: Charisma helps socially, you can boost your two best stats, and you get more skills. Solid.
• Half-Orc: You get a beefy Sherlock Holmes. Funny, but I’ll pass.
• Tiefling: Base tiefling isn’t great but see below (SCAG and Mordenkainen’s).

Dungeon Master’s Guide
• Aasimar: You get a WIS boost and a resistance, but the spells are lame.
• Eladrin: Fey step is nice, and you get intelligence.

Sword Coast Adventurer’s Guide
• Duergar: Meh. Only is viable if you’re underground.
• Deep Gnome: A different king of awesome than the Forest Gnome, but still awesome all the same.
• Ghostwise Halfling: Perfect stat boost and funky psychic abilities.

Volo’s Guide to Monsters
• Aasimar: Charisma is not great, and only Protector Aasimar is ideal, but all the other features are awesome.
• Firbolg: The WIS is nice, but STR is not.
• Goliath: Oh, Professor Grog…
• Kenku: Absolutely perfect stats and abilities, and I love Kenkus from a roleplaying standpoint.
• Lizardfolk: The stat boosts are fine, but all the features don’t help, and Lizardfolk have too many features in my opinion.
• Tabaxi: DEX and some pretty nice features. Gotta have a curious cat.
• Triton: Cool features but the stats are kinda lame.

Volo’s Monstrous Races:
• Bugbear: STR isn’t much, but the reach and the ambush potential is awesome.
• Goblin: The stats are good and I like Fury of the Small, but Nimble Escape is Cunning Action-redundant.
• Hobgoblin: Stat boosts are okay, and Saving Face is good for a rogue.
• Kobold: There’s DEX, Pack Tactics balances out the Sunlight Sensitivty, which however messes up your Perception in the daylight.
• Orc: -2 to INT? It’s even worse than a half-orc.
• Yuan-ti Pureblood: There’s INT, but you’re casting with a dump stat, and advantage on all magic is overpowerd in my opinion.

Elemental Evil:
• Aarakocra: Even better than a wood elf, as you can fly and stay out of danger.
• Air Genasi: Good stat increases, and the spells are nice.
• Earth Genasi: The abilities aren’t quite good enough.
• Fire Genasi: Boosts to INT and CON, you get fire resistance, and backup fire spells.
• Water Genasi: Boosts to WIS and CON, you get acid resistance, and probably even better spells.

Mordenkainen’s Tome of Foes – I gotta say I love these races in general.
• Eladrin: Fey step is based off CHA, but it’s still a pretty cool subrace.
• Sea Elf: Cool, but is kind of lackluster if you’re not in an aquatic campaign.
• Shadar-Kai: Arguably a better choice than the Eladrin, as you get a resistance and an even better teleportation.
• Githyanki: You could certainly do worse for a STR rogue.
• Githzerai: Doesn’t have a DEX bonus, but you get INT, WIS, and some pretty nice defensive features.
• Tiefling: Perhaps my favorite addition: with more options the Tiefling is more fabulous than ever. This is despite there only being a couple of viable options for this subclass.
o Asmodeus: See Player’s Handbook
o Baalzebul: Not useful
o Dispater: CHA only helps you socially, but you have DEX and perfect spells.
o Fierna: Meh
o Glasya: Basically same awesomeness as Dispater.
o Levistus: The defenses aren’t enough to cover it.
o Mammon: Not useful.
o Mephistopheles: Not useful.
o Zariel: The smite spells are the only saving grace.

Races of Ravnica:
Centaur: Nothing useful.
Goblin: See above.
Minotaur: Nothing useful.
Simic Hybrid: Fantastic and versatile.
Vedalken: They don’t get DEX, but their mental features are too good to pass over.

[TakeitVillain]

Part 3- Skills, Backgrounds, and Equipment

Skills
• Acrobatics (DEX). Definitely dependent on the DM, but you’re good at it.
• Athletics (STR). Same as above, but with STR. You could take it to make sure you climbs, swims, and jumps don’t go horribly wrong.
• Deception (CHA). I don’t really see Inquisitives as the lying type, but I could be wrong.
• Insight (WIS). This skill. It is required that you take this is and Expertise it, since it powers your Insightful Fighting. It’s what you do.
• Intimidation (CHA). For interrogations? Maybe.
• Investigation (INT). Want to be good at clueing for looks? This is how you do that.
• Perception (WIS). You have the WIS, you’ll need it, you’ll take it, and it’ll save you and your party. No questions asked.
• Performance (CHA).Performance is for Bards.
• [/COLOR][/B]Persuasion (CHA) You’re not really a face.
• Sleight of Hand (DEX). Situational depending how much you want to steal things.
• Stealth (DEX) Actually not as important for Inquisitives, but still, you’re a rogue.

Backgrounds

I’m mainly just going to address backgrounds that could cater to rogues and Inquisitives themselves, so you won’t see all of them. As an Inquisitive, we now know what skills are good, but you’ll need languages and background perks to aid your vast knowledge.

• Acolyte. Insight and Religion are decent options for you, and the extra languages are nice.
• Charlatan. Not bad skills for a rogue, but not crucial for you specifically.
• City Watch. The standard version only gets you insight, but the Investigator Variant is perfect for you.
• Cloistered Scholar. Decent skills and languages like the Sage, and also gets you access to restricted information.
• Courtier. Awesome face skills, and good potential if you want to involve yourself in politics.
• Criminal. Always a perfect rogue choice, and you could potentially switch out the Thieves’ Tools.
• Faction Agent. Perfect customizable skills, and you can be a perfect consulting detective for your faction.
• Far Traveler. Perfect skills and a language, though the tool proficiency is iffy.
• Guild Artisan. Good face skills that will help you socially, a language, and tool that could be useful.
• Inheritor. Survival is kind of a weird choice, but otherwise it works.
• Mercenary Veteran. A good choice to cover some weak points.
• Noble. Not really that useful.
• Sage. You get some great knowledge skills, two languages, and the research perk is awesome for you.

Equipment

Armor
• Studded Leather. No need for normal leather. This is generally the superior stuff you’ll be wearing.
• Medium Armor. If you’re not focusing on DEX (which is unlikely), this is helpful. You want to be somewhat stealthy, so only go for hide, chain shirt, and breastplate, which is the optimal choice.
• Heavy Armor. Just no.

Weapons – Keep in mind that Insightful Fighting muddies the bonus action attacks, but that’s not a huge issue.
• Crossbow, Hand. Awesome if you’re going for the Crossbow Expert feat; otherwise don’t bother.
• Crossbow, Light. The go-to ranged weapon. The range is the same as a shortbow with a better damage die, and the reload property generally doesn’t matter for rogues.
• Dagger. Dagger, dagger! Highly versatile, whether concealing, throwing, or two-weapon fighting
• Longsword. This only reason rogues are proficient with this is so they can use Sunblades, which is an okay reason.
• Rapier. The go-to dueling weapon.
• Shortsword. Ideal for two-weapon fighting, but you can’t throw them.
• Shortbow. It’s a trap!
• Whip. You’d have to be willing to use up a feat for this kind of flavor.

[TakeitVillain]

Feats and Multiclassing

Feats – Although, the Inquisitve suffers from MADness, it is also a subclass that loves feats. In order to truly shine, I recommend grabbing at least one by level 12. I only will go over the feats that could potentially apply to the Inquisitve Rogue.

• Alert. It’s awesome and fits your build.
• Crossbow Expert . A great option if you want to wield a hand crossbow; otherwise, you don’t need it.
• Defensive Duelist. Very tempting for melee rogues, but it competes, with Uncanny Dodge.
• Dual Wielder. All this allows to do is duel wield rapiers and get an AC bump. Not really worth it.
• Dungeon Delver. In a duneon-heavy campaign, this is perfect for you.
• Durable. Leave this to your party’s front line.
• Inspiring Leader. Good, but you need decent CHA, which you proabably don’t have.
• Lucky. Always a solid choice.
• Magic Initiate. This is always a good feat, but for the Warlock version of this, I’m tempted to go gold.Why? A la Hex spell, you get extra damage, and, as part of Insightful Fighting, your enemy can have disadvantage on their Deception Check, which means you are almost guaranteed to SUPER SNEAK ATTACK.
• Moderately Armored. Like I said , it’s unlikely that you won’t be boosting DEX.
• Observant. For the Inquisitve, this is how you become a god. Plus, you can read lips.
• Resilient. If you have an odd CON score in need of boosting, this is a solid choice. The others you don’t really need.
• Ritual Caster. You won’t spellcast enough to use this.
• Savage Attacker. Rogues don’t have large damage die, so this is a bad feat.
• Sentinel. Only if you really want to be a tank, but you also have Uncanny Dodge.
• Sharpshooter. Absolutely fantastic for archer rogues. You will do some crazy damage with sneak attack. This is best used when you have advantage.
• Shield Master. This doesn’t really apply to you.
• Skilled. Inquisitve need more knowledge skills, and with Reliable Talent, this is awesome.
• Spell Sniper. You can’t use sneak attack with spells.
• Weapon Master. You have all the weapons you need.

Note: I want to include the Xanathar’s racial feats, since they’re really awesome, but you can check EvilAnagram’s optimization guides (ranger guide is most accurate). They have a pretty good run down of those.

Multiclassing

If you haven’t noticed, the Inquisitve Rogue has some pretty awesome features, and I find Eyes for Weakness and Stroke of Luck awesome enough that I’d rather single class it. However, these are some pretty high-level features, and most games don’t go that high. Multiclassing is for those moments or if you feel like you need something different.

• Barbarian. No
• Bard. CHA is a dump stat, but it makes you a better skill monkey, and Inspiration is always good.
• Cleric. A great pick for your focus on Wis, and the spellcasting is nice. I’d probably go for Life or Knowledge Domain.
• Druid. Again, a WIS caster, although I think there’s not as much synergy as the cleric, but that’s just me.
• Fighter. Giving you more solid damage and a better tank, and action surge. I like it. Battlemaster and Eldritch Knight are the most flavorful choices.
• Monk. You weapon attacks can potentially go up in damage, you likely get better AC, you’re faster, and you can stun things. Hell yes.
• Paladin. Aren’t you MAD enough already?
• Ranger. With natural explorer, favored enemy, and Hunter’s Mark, I can’t think of a better Sherlock in the woods. Gloomstalker would be a good choice. I highly recommend getting Nature and Survival somewhere.
• Sorcerer. Spellcasting with your dump stat is a bad idea.
• Warlock. Again, dump stat, but not the worst choice when you could get weapon cantrips, Hex, and cool invocations.
• Wizard. Syncs with INT, and you could lighten the load of the other mages in the party. Not bad.

Hope you enjoyed this guide! To finish it off, here’s an example build.

Variant Human Inquisitive Rogue 20
• Starting Stats. Str 8, Dex 16, Con 12, Int 14, Wis 14, Cha 10
• Variant Feat: Magic Initiative (Warlock: Booming Blade, Minor Illusion, Hex)
• Weapons: 2 daggers, rapier, light crossbow.
• Background: Criminal
• Skills: Acrobatics, Deception, Insight (Expertise lvl1), Investigation (Expertise lvl6), Perception (Expertise lvl1), Stealth (Expertise lvl6)

Already by level 3, this guy gets a 16 average Insight (14’s the minimum), and 16 Passive Perception, and he’s darn fine at combat too. With Hex and Insightful fighting, his average crossbow attacks do an average of 19 damage (I’ve done the math), and it’s 24 average if Booming Blade goes off on the Rapier. Not broken, but pretty darn nice.

[TakeitVillain]

Please feel free to look through this, as this is one of the few guideson inquisitives. Plus, give me feedback!