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Message: <blockquote data-quote="Guest 6801328" data-source="post: 7246051">And if multi-classed with Rogue, how deep?The main reasons I would want to dip rogue are:Expertise (1 and 6).  Double proficiency at Stealth is just awesome, but perhaps overkill (or perfect kill?) when combined with Pass Without Trace.  Top contenders would be Stealth, Perception, and Acrobatics.  (Perception is probably "optimal" but maybe less fun/flavorful.)Sneak Attack.  (1 and 5).  This amply compensates for smaller Monk damage die.Uncanny Dodge (5) Simply awesome damage reductionAssassinate (3, assuming that sub-class) Ironically half of it is largely redundant: you already get Advantage for Bamfing into range, so Advantage vs. anybody who has not yet had a turn isn't so great.  However, this is also the supreme Surprise class, so the automatic crit is amazing.Cunning Action is less useful, both because it is somewhat redundant with Step of the Wind, and because it consumes the same bonus action that is the whole point of being a shadow monk.  Who needs Disengage when you can teleport at will?  (Ok, shadows won't always be available...)Beyond level 6 the next really great ability is Blindsense at 14.  And while Shadow Monk 6/Rogue 14 is also a cool option, I'm trying to focus on the Monk here.So the likely candidates would be level 1, 3, or 5.  Downsides of multi-classing: - In general, delayed Monk abilities.   - Lost ASIs.  Rogue 3 and 5 ultimately cost one ASI.  On the other hand, designing for Level 20 is, let's face it, kinda dumb.  So the other way of looking at it is that Rogue 1 and 5 delays ASIs by one level, Rogue 3 by 3 levels. - No Shadow Monk capstone at Rogue 5.  A Rogue 3 you'd keep the capstone, which has huge synergy with Sneak Attack, but for only 2d6.Summary:Rogue 1 gets you 1d6 Sneak Attack and Expertise (plus a bonus proficiency and some decent ranged weapons if you start Rogue) and minimizes impact on Monk progression.Rogue 3 gets you Assassinate which is great but, unless you are playing a solo game, not very reliable.Rogue 5 doubles Sneak Attack and gets you Uncanny Dodge Looking at all that, and weighing against the downside of delaying Monk levels, I think Rogue 1 is my favorite. If I'm going to go deeper than that I'd go all the way to 5.Thoughts?  Experience?Oh, and race-wise I love variant Humans (Mobile?  Lucky?) and Wood-elfs are practically designed for monks, even if the RP is...weird.  But I'm really jonesing to play a SCAG variant Tiefling (with Dex instead of Cha) just so that I can make a Bamf! noise every time I shadow step.  Also, Acrobatics with a tail makes for good RP.</blockquote>

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