2024 Monk Heightened Focus: Step of the Wind

So I wanted to ask as I'm a little confused. 

Step of the Wind. When you expend a Focus Point to use Step of the Wind, you can choose a willing creature within 5 feet of yourself that is Large or smaller. You move the creature with you until the end of your turn. The creature’s movement doesn’t provoke Opportunity Attacks.

According to this I can basically yoink a willing ally and with my insane movement as a monk can dash 100ft away with them? Do they stick to the same side? Do I get to choose where to place them? Can I run across water with them? How about fly? I'm curious if I'm really able to just whisk an ally out of danger or dash into a horde using this feature.

Hi!

Do you know if you can move a willing character with step of the wind (heightened focus) that is being grappled?

Thanks!

Quote from Arkul_Freedom >>

Hi!

Do you know if you can move a willing character with step of the wind (heightened focus) that is being grappled?

Thanks!

 Grappled by an enemy? IMO the willing character should be freed before being moved.

Quote from TarodNet >>

Quote from Arkul_Freedom >>

Hi!

Do you know if you can move a willing character with step of the wind (heightened focus) that is being grappled?

Thanks!

 Grappled by an enemy? IMO the willing character should be freed before being moved.

The official rules on how exactly a creature can be freed from a grapple by someone else are frustratingly vague. I think if I were DMing I'd let the Monk do this if they succeed on an Athletics check against the grapple escape DC, or something like that.

Quote from wagnarokkr >>

Quote from TarodNet >>

Quote from Arkul_Freedom >>

Hi!

Do you know if you can move a willing character with step of the wind (heightened focus) that is being grappled?

Thanks!

 Grappled by an enemy? IMO the willing character should be freed before being moved.

The official rules on how exactly a creature can be freed from a grapple by someone else are frustratingly vague. I think if I were DMing I'd let the Monk do this if they succeed on an Athletics check against the grapple escape DC, or something like that.

 I totally agree. It'd be nice to have a rule for that.

Raw forced movement doesn't usually care about outside factors. Also, given that at the level that a monk gets that feature of step of the wind they can disengage and dash at the same time.. I'd just let them use the point to move the ally, freeing them from a grapple. Things only do exactly what they say they do. So unless the monster stat block states the grappled or another creature can use an action to break a DC x yadda yadda, there is nothing preventing someone else from breaking it with forced movement. Monks are easily now amongst the top 3 buffed classes to straight play now in 2024 with almost every single level adding significant improvements. If your monk wants to be a mobile chess player moving players (pawns) about the board. let them shine fam. IMHO