
ojamojallo |

So I'm making a level 7 hunter with a roc as animal companion. I'm fully aware that grappling in mid-air is a bit of a grey area, so let's assume the following, without arguing whether or not it is possible: My roc flies in, grapples an opponent. Next turn he maintains the grapple and uses his action to fly away half speed. opponent get's save for enterering hazardous area, ect.
Now let's assume the roc serves as mount, and I'm riding it with my longbow in hand firing arrows down at my enemies in the fanciest way imaginable.
So assuming that is all possible, can I ride my roc during the grapple?
Or in other words, can I ride a flying mount while he is grappling?

CommandoDude |

Yes. Just note you are drawing AoOs for those longbow attacks since you are adjacent (ie riding your mount therefor occupying your mount's space) to an enemy.
Also you will probably want to keep an eye out for encumbrance. Unless you really boost your roc's STR he might get encumbered from essentially carrying two people.

Game Master |

I'm fully aware that grappling in mid-air is a bit of a grey area
Except that it isn't. It works precisely the same as the rules say it does, and they never demand that you be standing on the ground.
As for the AoOs, you share your roc's space. Any space that the roc occupies, you occupy while riding it. That's just the rules of mounts - GM can make an exception in this case, but it doesn't matter - grappled creatures can't take AoOs.

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I used to watch an Osprey (we called him "Johnnie") up at my family's cabin during the summer. He'd usually just catch fish, or harry the Bald Eagle that also resided there, but sometimes he'd grab a snake swimming on the surface. If you've ever watched a bird trying to carry off large, struggling prey, it's quite clear that the grapple isn't one-sided, and that the bird doesn't just use its talons.

Joesi |
I'm not sure if you're considering this, but you should ensure that the combined weight of you, your gear, and the target it's grappling is below that of it's light weight carrying capacity, otherwise it will start falling during the grapple (and I think I recall that falling is like 200 ft per round or something?)