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Can a Rogue Inquisitive use their passive Insight with Insightful Fighting?

Insightful Fighting short version: as a bonus action, make a Wis (Insight) check contested by target's Cha (Deception) check. If you succeed you can deal Sneak Attack damage vs target for 1 minute or till Insightful Fighting is used on another target.

Passive Wis (Insight) = 10 + Wis mod + Proficiency Bonus if any

I don't really see any reason why you can't, specially if you have Expertise (2x Proficiency Bonus) with Insight. I know this would be useless later, but for now at lower levels, it seems viable to do so. My current Inquisitive has a passive Insight of 17 ([Proficiency Bonus x2] 4 + Wis mod 3 + 10. I just would like to if it a legal to do.

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This is not the right use for a passive check

Passive Checks (p. 175, PHB) defines when to use a passive check

A passive check is a special kind of ability check that doesn’t involve any die rolls. Such a check can represent the average result for a task done repeatedly, such as searching for secret doors over and over again, or can be used when the DM wants to secretly determine whether the characters succeed at something without rolling dice, such as noticing a hidden monster.

Here, you actively want to do something, its not the DM who wants to secretly determine if you hit or not. Also, the attack is not a task done repeatedly, in the sense described above -- that you try something for a longer time frame again and again, until you hopefully succeed. In combat you determine the outcome for each attack separately. Your action is not a passive action, it is active. This is not what the passive check is for, so you have to roll an normal check for the contest.

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    \$\begingroup\$ Also worth noting that allowing "passive" checks in this case would almost fully negate the power of the 11th level Rogue ability Reliable Talent. \$\endgroup\$
    – biziclop
    Jul 24, 2023 at 10:59
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    \$\begingroup\$ If the idea of passive checks is applied to insight, why wouldn't it act as a floor in the way it does for perception? rpg.stackexchange.com/questions/48281/… \$\endgroup\$ Jul 25, 2023 at 4:24
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    \$\begingroup\$ @DanJurgella Because that guidance is not good? \$\endgroup\$
    – Yakk
    Jul 25, 2023 at 13:44
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    \$\begingroup\$ @DanJurgella I think this is an excellent question, and the space in the comments is entirely inadequate to do it justice. I therefore put my thoughts about it in a new answer on the question you linked. \$\endgroup\$ Jul 26, 2023 at 9:51
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    \$\begingroup\$ @DanJurgella You to linked guidance on how to use passive perception. Then asked why you wouldn't apply it to insight. I stated that the guidance you linked on how to use passive perception is not good guidance, which I believe is a sufficient argument asto why passive insight shouldn't be used as a floor to insight, thus answering your question. This is not a place to argue about that guidance - I'm just answering your question why your argument isn't a slam-dunk. \$\endgroup\$
    – Yakk
    Jul 26, 2023 at 13:03
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No; this is like a Contest - opposed ability checks

In Chapter 7 of the PHB (p. 174) an opposed ability check is described under "Contests." In these situations, one creature attempts to do something (ability check) while being opposed by another creature (ability check). A very common example of this is the Grapple during combat.

The mechanical impact of this rogue feature - Wisdom (Insight) opposed by Charisma (Deception) - is a Contest. Treat it as such, per the Chapter 7 section on Contests.

Both participants in a contest make ability checks appropriate to their efforts.

(Which ability checks are used is spelled out in the feature description, Wis(Perception) versus Cha(Deception).

They apply all appropriate bonuses and penalties, but instead of comparing the total to a DC, they compare the totals of their two checks. The participant with the higher check total wins the contest. That character or monster either succeeds at the action or prevents the other one from succeeding.

Successful check by the rogue yields the desired the result, failure does not, and a tie goes to the rogue's opponent.

If the contest results in a tie, the situation remains the same as it was before the contest. Thus, one contestant might win the contest by default. If two characters tie in a contest to snatch a ring off the floor, neither character grabs it. In a contest between a monster trying to open a door and an adventurer trying to keep the door closed, a tie means that the door remains shut.

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