Insight in 5e – How It Really Works & Best Times To Use It

If you search the Player’s Handbook, Basic Rules, or the Dungeon Master’s Guide for the word “Insight,” you’ll find the word comes up mostly in context of what your character learns as they grow.

It literally means the general knowledge your character gains from life and experience. Few of the results actually concern the Insight Skill and its uses.

Mechanically speaking, Insight seems pretty limited, but with a little insight and by asking the right questions, you can gain game-changing knowledge. 

What Is Insight in Dungeons and Dragons 5e?

Insight is a skill check that you can make to discern if there is something missing. Is this NPC lying to me? Is the BBEG using some sort of strategy, and what is their next move?

These questions can all prompt a Wisdom (Insight) check from your DM to reveal information to you.

For those players who remember Dungeons and Dragons 3E, Insight is the generalized inheritor to the old skill Sense Motive. Sensing a motive is only one thing you can do with an Insight check, but it is not the only thing. 

From the Basic Rules:

Your Wisdom (Insight) check decides whether you can determine the true intentions of a creature, such as when searching out a lie or predicting someone’s next move.

Doing so involves gleaning clues from body language, speech habits, and changes in mannerisms.

This is all you get from the Basic Rules when you look it up. Not much to go on, is it?

It seems that outside of these specific situations, Insight is not a useful mechanic in which to base a character, especially when, as a player, you can figure things out without needing to be told. 

Yet hidden inside this seemingly meager tool is a hidden gem that you can leverage, both as a player and a DM.

Rules As Written

What do these rules offer us, then? Quite a bit, actually. How often have you been double-crossed by an NPC (I’m looking at you, Strahd)?

It’s probably a safe bet to make an Insight check the first time you meet an NPC or the first time they state their agenda. 

First, I can’t tell you how I’ve been led astray by a little guy with a bad cough who was supposed to be showing me where I can melt down some precious jewelry, but instead, he got me trapped by a giant spider.

He even threw my rations down a cliff and made me turn my back on my best friend in the world. A good Insight check would have changed that whole situation. 

Secondly, Insight can help you guess an NPC’s next move. Will they shoot the hostage? Will they try to run away? Will they dive for the macguffin or try to shoot me instead?

Answering questions like this can help you decide what your best course of action is. 

Going Beyond the R.A.W.

The beautiful thing about Dungeons and Dragons is that it really is a simple game.

If Wizards of the Coast wanted, they could have made a rule for everything, like the guys over at Paizo did with their amazing game, Pathfinder.

But they didn’t, opting instead for the players and the dungeon masters to have the freedom to do what feels right and improvise in order to let the play continue instead of getting bogged down in research.

There’s nothing so frustrating as being up to your chin in rule books when you really just wanted to do some parkour and pickpocket a guy after studying him for a round to determine the best moment. 

Dungeons and Dragons avoids that with this neat little rule here:

Remember that dice don’t run your game – you do. Dice are like rules. They’re tools to help keep the action moving. At any time, you can decide that a player’s action is automatically successful.

You can also grant the player advantage on any ability check, reducing the chance of a bad die roll foiling the character’s plans.

By the same token, a bad plan or unfortunate circumstances can transform the easiest task into an impossibility or at least impose disadvantage.

Ideally, if you can describe what you are doing and suggest a roll for the DM, they will set the DC and let you roll it. When this type of trust and communication occurs, all kinds of uses for Insight open up.

When that happens, understanding when to use Insight is determined by when to use Wisdom instead of Intelligence. 

Intelligence vs. Wisdom

Let’s say your players are making their way through the lair of an evil wizard, and they do not have a single arcane spellcaster in the party.

No one can walk through the lab and roll a decent Arcana check to figure out the Wizard is researching alchemical processes to make themselves into a dracolich by first polymorphing into a dragon and then using a special phylactery.

At least, they can’t look at the notes and the ritual book to find that out. 

But let’s say, for instance, there is a Druid or a monk in the party with a high Insight score.

They search the room and they find lots of tomes and trinkets of dragons, vampires, undead, and special skin creams (you know, for keeping the body fresh).

They have also seen this Wizard in the past casting polymorph and become a dragon.

The wizard’s lair was full of undead. Perhaps the wizard is a Dragonborn or a Kobold, and they have said things like, “Curse this living flesh,” or something equally creepy.

Instead of an Arcana check, ask these players for an Insight check to put it all together. 

The Dungeon Master’s Guide will tell you that the difference between Intelligence and Wisdom is a character’s ability to notice what is around them (wisdom) and knowing what the signs mean (intelligence).

This distinction works for ability checks such as Investigation and Perception, but when it comes to Insight versus a knowledge check such as Arcana or Religion, what we are really talking about here is the difference between linear and interconnected reasoning. 

With linear reasoning, we can look at the spell book in the evil wizard’s lair we mentioned above and see that True Polymorph plus Wish plus Soul Cage equals ambitions of dracolichdom.

With interconnected reasoning, we can see a Venn diagram composed of three circles: a necromancer, a dragon aesthetic, and a phylactery; and we can think, “Dracolich!”

This is the difference between logic and intuition, or intelligence and wisdom, or knowledge and insight.

Knowledge understands the formula for deducting a probable answer. Insight makes the connections for inducting a probable answer.

This is Inductive versus Deductive Logic, which is a fascinating study in and of itself. 

Therefore, don’t hoard the secrets for your so-called smart characters in the party. There’s more than one type of genius out there.

Incite Insight - DnD 5e
© Wizards of the Coast by David Sladek

Feats, Spells, Items and Class Abilities

The majority of feats, spells, items, and class abilities that use Insight do so in a defensive way, which makes sense, after all.

Our characters have a Passive Insight which should be rolled every time someone rolls a Deception check against us. 

There is only one exception to this, but it is a grand one! The rogue subclass Inquisitor uses Insight in an offensive, strategic way.

At 3rd level, they gain an ability called Insightful Fighting, which allows them to make an Insight check versus the target’s Deception check. If successful, they gain Sneak Attack for one minute against that target.

Insightful Fighting

At 3rd level, you gain the ability to decipher an opponent’s tactics and develop a counter to them.

As a bonus action, you make a Wisdom (Insight) check against a creature you can see that isn’t incapacitated, contested by the target’s Charisma (Deception) check.

If you succeed, you can use your Sneak Attack against that target even if you don’t have advantage on the attack roll but not if you have disadvantage on it.

This benefit lasts for 1 minute or until you successfully use this feature against a different target.

This is the reverse of the Battle Master’s Feinting Attack ability, which allows you to make a Deception versus an Insight check to gain extra damage and advantage.

The obvious advantage to the Inquisitive’s Insightful Fighting ability is the bonus sneak attack every round.

Let’s take a look at one sample character who maximizes this ability to deal extra damage to a single target and win the day.

Rook, the Kenku 

Rook is an observant kenku who has a knack for finding people. The mountain where Rook’s hometown sits is near a portal to a particular place in the Shadowfell where dark fey like to dwell and cross over.

It is not uncommon for dopplegangers, shapeshifters, and fey who make much use of charm and Deception to cross over and predate upon the citizens of Rook’s beloved city.

To this effect, they have become both a guardian of their city and a hunter of those who would hunt on the people therein. 

Rook has maximized their Insight skill. First, it will help them should a fae be lying or disguised.

Second, Rook’s 3rd-level rogue ability Insightful Fighting allows them to see through these disguises and tricks in combat so they can take full advantage of their discerning nature.

And finally, Rook has multi-classed as a ranger to add the favored enemy and terrain bonuses to tracking their quarry, the specific damage bonus allowed by Hunter’s Mark, and the Favored Foe ability from Tasha’s Cauldron of Everything.

Not much gets past Rook, and they can easily be an NPC antagonist or an inspiration for your own character. 

Final Thoughts

Insight is much more than it appears, and if you can take advantage of it at your table, your character can shine in unexpected ways.

Don’t let the wizard or the bard have all the fun figuring out all the puzzles and putting the clues together.

You don’t need to be smart if you can be insightful