So I am about to drop into a campaign in progress, they are something like 33 sessions in. I am taking this opportunity to play a character race and class that I have never done before, and doing such in a non-meta manner.

Standard Tiefling - Kensei Monk (7) Inquisitive Rogue (3)^2

Now, I can already feel your eyes burning into the screen, but hear me out... the passive bonuses from the Kensei (Agile Parry) is free, so I can use my BA to proc Insightful Fighting (and as long as it succeeds) get Sneak Attack on the two attacks to follow (as it lasts for a minute and does not say it is limited to ONE attack, as per the usual SA rules^1.) That just seems too good to pass up. A free +2 to AC (taking me from 18 to 20 - DM gave me a RoP ) on top of two attacks for 10 rounds of combat or until incapacitated whichever comes first of sneak attack damage?

With playing a race that doesnt necessarily have the best spread for Monks... I can see this working out fairly well.

As a side, DM gave me a pretty snazzy Katana option, which I gladly took. Lol.

1. This may vary based on Flanking and other rulings set into your personal game. Room for error on this specific example may be greater than I implied.

2. This could very well be a standard meta build for Monks, just not the race selection.

I think that’s an optimistic reading of Insightful Fighting as I can’t see where it infers the limitations of 1 sneak attack per turn don’t apply, as for example the Rogue - Scout’s 17th lvl ‘Sudden Strike’ explicitly does. Have a think how liberal your DM is and you might find you could get away with it - fingers crossed!

Quote from Mongolian_dude >>

I think that’s an optimistic reading of Insightful Fighting as I can’t see where it infers the limitations of 1 sneak attack per turn don’t apply, as for example the Rogue - Scout’s 17th lvl ‘Sudden Strike’ explicitly does. Have a think how liberal your DM is and you might find you could get away with it - fingers crossed!

 I would agree, sneak attack explicitly says once per turn. Insightful fighting just says you can use it to sneak attack even if you don’t have advantage so you would still be limited to once per turn but can sneak attack once per turn for one minute on the target if they last that long 

Edit: Also what are you making the sneak attacks with? Sneak attack requires finesse weapon which a katana wouldn’t be (if it’s just a reflavored longsword) unless it uses homebrew or shortsword stats. Your unarmed strikes do not count either

The Katana is homebrewed to allow it to be Finesse. So to be more precise, it'd be the following round of attacks, and not necessarily the attacks of that turn as to still get the AP to proc.

Good catch, should have stated that in the Original.

Here is the direct quote of Insightful Fighting with highlights to show my thinking

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 can 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.

With that specific thread of text, it states on the attack roll. As a monk, you get an Extra Attack per Attack Roll at level 5. Although I have highlighted in blue to where I may be reading too far into the flavor of the ability. To me, developing a counter would mean that you would be able to proc the extra damage because you took the gamble on using your Bonus Action to study them and learn their movements to do so.

Granted, to continually proc Agile Parry, this Sneak Attack may not always apply... but if I wanted to just utilize my Kensei Weapon (which in my case is considered Finesse) I could proc it twice.

The way I read it is that the insightful fighting allows you an additional way, if you succeed on your contested check, to use your sneak attack. Normally, you need advantage or an ally within 5 feet of the target. This just gives you an alternate way but does not change the rules for sneak attack which allows it only once on your turn. No matter how many attacks you have. And you wouldn’t be able to use agile parry the same turn as it requires you use an unarmed strike and defend with your katana and unarmed strikes don’t count for sneak attack. Edit: you could, however, BA insightful fighting, attack once with your katana (sneak attack) and your second attack (from extra attack at 5th level) use unarmed strike and get the AC bonus. Maybe that was what you were getting at and I misunderstood. 

But I could be wrong and would be best to discuss it with your DM. 

The train of thought for a round of combat in my head went like this;

Move into combat - Bonus Action Insightful Fighting - Katana Attack 1 - Unarmed Attack 2 - Proc Agile Parry - End Turn

I may have just read too far into the flavor of the ability itself, but I'll talk to the DM about it. See what happens.

No being as awesome as I had anticipated. The rules of Sneak Attack overrule the flavor text of Insightful Fighting.

You guys won lol disappointing byt to be expected.

Quote from Grim_Motive >>

The train of thought for a round of combat in my head went like this;

Move into combat - Bonus Action Insightful Fighting - Katana Attack 1 - Unarmed Attack 2 - Proc Agile Parry - End Turn

I may have just read too far into the flavor of the ability itself, but I'll talk to the DM about it. See what happens.

 That should work for your katana getting the sneak attack. The unarmed strike would not but is enough for the Agile Parry to go into affect. On subsequent rounds you would still only get one sneak attack on your turn ( you could get additional sneak attack if target provoked an Opportunity Attack since it isn’t your turn)

Frankly, even if Insightful Strikes worked the way you said I don't think the MC would be worth it. You'd be much better off going 10 levels of Kensei and setting yourself up with maximum Ki and to pick up Sharpen the Blade next level. Plus you get to run on walls.

Quote from HeironymusZot >>

Frankly, even if Insightful Strikes worked the way you said I don't think the MC would be worth it. You'd be much better off going 10 levels of Kensei and setting yourself up with maximum Ki and to pick up Sharpen the Blade next level. Plus you get to run on walls.

 Think I'd agree. Both Rogues and Monks suffer more than most when it comes to multi-classing, since your Ki points total and Sneak Attack damage dice are tied to your class level, rather than your character level.

Keep in mind that any turn you are not using your bonus action for triggering insightful strikes against an opponent or using some ki or rogue ability you can in fact use that bonus action to get a second unarmed strike.  So if you find yourself being more stationary you can get three strikes in rather than just the two.  This is provided by your martial arts.

Quote from Fateless >>

Keep in mind that any turn you are not using your bonus action for triggering insightful strikes against an opponent or using some ki or rogue ability you can in fact use that bonus action to get a second unarmed strike.  So if you find yourself being more stationary you can get three strikes in rather than just the two.  This is provided by your martial arts.

 Yeah, thats essentially the plan.

As far as as playing a Monk & Rogue together...

I try to stay away from "meta" builds as I personally do not find them fun, but I plan on going further into Monk from this point forward. Unless there are other options in the Rogue line that come up that interest me. My character is more so being built to be a bruiser and sneaky, works with my backstory choices/background

Playing a single class 1-20 is not a "meta" build. Choosing weird and/or ineffective multiclass options is not the only way to subvert the norm. With the right background and feats (skill expert, prodigy, observant, alert, telekinetic, shadow touched, fey touched, magic initiate, etc) you could easily create a Kensei that plays like a rogue.

All that being said, have fun with your build! I haven't had the chance to jump in with a higher level character in a long time and it is so fun being able to have your multiclass already set up. Honestly a bit jealous.

Quote from HeironymusZot >>

Playing a single class 1-20 is not a "meta" build. Choosing weird and/or ineffective multiclass options is not the only way to subvert the norm. With the right background and feats (skill expert, prodigy, observant, alert, telekinetic, shadow touched, fey touched, magic initiate, etc) you could easily create a Kensei that plays like a rogue.

All that being said, have fun with your build! I haven't had the chance to jump in with a higher level character in a long time and it is so fun being able to have your multiclass already set up. Honestly a bit jealous.

 

  In terms of "meta build" I was more so referring to how it isnt necessarily an optimum build with Race and Multi-Class choices. As others have stated, there are much better ways to build a monk, and mine isnt the greatest. I like that. I think itll play out well. Lol

I have never jumped into a campaign at this level. So I am a bit nervous about it. Theres no build up to the fight difficulty, its just BOOM. There lol

Oh you definitely still have sweet things going for you. Cunning action on a monk is awesome. I mean, every monk is envious. I love having expertise on a character as well. And I'm sure your special finesse Katana is going to feel great to use.

I haven't done it since 3.5 when I got to join a campaign with my 4 class monstrosity of an archer build. It can be daunting but it's also just super fun. Some builds have horrible leveling progression but look great once you reach a certain point. It's nice to have a chance to explore one. For you, it's going to be great to have cunning action and extra attack already established.