[RPG] Can a Shadow Monk use shadowstep without breaking stealth

dnd-5emonkstealthvision-and-light

Got a battle royale coming up with my shadow monk (6 monk/2 rogue) and other friends with their PCs (all total level 8). The arena is divided into one area of darkness, two areas of dim light, and one area of bright light, each with varying degrees of cover.

My strategy going in is to load up on darts and daggers, stealth in dim light. Next turn shadowstep>dart (sneak attack)>dart>move. Then, dart>dart>hide>move. Rinse and repeat, attempting to be hidden as often as possible while not on my turn.

Would shadowstepping somewhere else in the darkness/dim light break my previous stealth roll (and thus negate my sneak attack die)? RAW I would expect this to be the case, however RAI I'm not so sure.

Figured I'd toss the question to the comparative experts.

Best Answer

When you try to hide, make a Dexterity (Stealth) check. Until you are discovered or you stop hiding, that check's total is contested by the Wisdom (Perception) check of any creature that actively searches for signs of your presence. (PHB 177, emphasis mine)

While any type of movement has the potential to "break" stealth (by walking out of cover for example), there is nothing in shadow step that would reveal your presence (like an attack), nor would it inherently mean that you stop hiding. So it does not automatically break your stealth, but depending on the circumstances, your DM might reasonably rule that it does or require a new stealth roll from you.