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Bugbears have long arms, allowing them to grapple enemies 10 ft. away.
The Bugbear's square is not in the effect range of the Wall of Fire. However, about 5 ft. worth of one of the Bugbear's hands is supposedly in a square that is.
Mechanically, does the Bugbear take damage? If so, simulationally, how do we reconcile that such a small fraction of the player being in the square and taking just as much damage as a character residing fully in the area of effect?
The Long-Limbed trait of the bugbear in Volo's Guide to Monsters states (VGM, 119):
When you make a melee attack on your turn, your reach for it is 5 feet greater than normal.
And the grappled condition on a creature can end either if the grappler is incapacitated, or
if an effect removes the grappled creature from the reach of the grappler
The Long-Limbed trait functions only on the bugbear's turn. What this means is that, by the end of the bugbear's turn, the grappled creature is no longer in the reach of the bugbear and simply no longer grappled by the bugbear.
You could also interpret this trait as saying "for this melee attack that you make on your turn" (probably the intended reading), and in this case your grapple with a target 10 feeet away would end imediately after having initiated it.
Nothing happens to the bugbear: the space occupied by them is where they are, even if the extended reach might let you think otherwise. You could say that the bugbear feels the dangerous heat of the magical fire scorching their arms, but it is not enough to damage them.
The same way, any creature with an extended reach remains in their space: this space does not extend to accomodate a "grapple" situation.
The space of a creature is determined by its size alone, even if it extends its arms outward (from Player's Handbook page 191):
A creature's space is the area in feet that it effectively controls in combat, not an expression of its physical dimensions.
By the rules as written, the bugbear is not in the area that causes damage, so it won't take damage.
One side of the wall, selected by you when you cast this spell, deals 5d8 fire damage to each creature that ends its turn within 10 feet of that side.
The bugbear is 15ft away.
A creature takes the same damage when it enters the wall for the first time on a turn or ends its turn there.
The bugbear is not entering the wall. It sounds strange, I agree. Another strange possibility is that another creature can cross the space with the bugbears arms without any issue, which again sounds strange.
Do the above make perfect sense? Not really. For these edge-cases, which are not covered by the rules (in this case, being able to grapple something that is 10ft away from you), the DM should use common sense and make rulings that the table agrees with.
Different groups will prefer different approaches. At my table, I'd make the bugbear not take any damage, and the grappling space with his arms would be difficult terrain (if some other creature decided to run across it somehow). Another reasonable ruling would cause damage to the Bugbear but grant him a Dexterity save. Other tables would come to their own conclusions.
PS: as the other answer stated, this 10ft grapple is only valid on the bugbear's turn, when it attacks. After that, the enemy is no longer grappled. So most of the argument is pointless, the Bugbear will not end its turn inside the "danger zone".
As some of the other answers have correctly stated, the Bugbear does not have any ability to grapple at further than the usual 5 feet -- but let's lay that quibble aside. Let's just assume you've polymorphed your ally into a giant and address the real question of whether sticking an arm through a wall of fire will burn.
As written in the wall of fire spell text, "a creature takes the same damage when it enters the wall for the first time on a turn". Does entering require moving your space into the wall, or does reaching through it count as 'entering'?
Well, the rules aren't really clear on that point, but that's okay. The DM can and should make that call. Does it make sense in the context to get burned when you shove your arm through a literal wall of fire? Well, yeah, obviously. So it's entirely reasonable for the DM to rule that the grappling creature gets burned in this case.
It would be equally reasonable to rule that the character takes only half damage from this action since they're exposing less than their entire body to the flames, but then you have to deal with some weird corner cases, like making sure your PCs don't abuse this ruling by sticking an arm in for half damage, and then walking through since they already took the wall damage and it only deals damage the first time they enter it each turn.
Personally, I'd just say the wall does its full damage, whether you stick an arm through or your whole body, but that's really down to how you want to run your game.
To be honest, I would be pretty annoyed if my DM decided sticking an arm into a flaming wall doesn't do damage; that feels like rules lawyering of the most ridiculous kind, to claim you didn't get burned because the square that represents your character's "space" didn't technically move across the line.
TLDR: What is "inside" in this context? Also, Wall of Fire is a confusingly written spell.
This seems very clear cut to me. The text of the spell is:
You create a wall of fire on a solid surface within range. You can make the wall up to 60 feet long, 20 feet high, and 1 foot thinksic, or a ringed wall up to 20 feet in diameter, 20 feet high, and 1 foot thick(1). The wall is opaque and lasts for the Duration.
When the wall appears, each creature within its area must make a Dexterity saving throw. On a failed save, a creature takes 5d8 fire damage, or half as much damage on a successful save.(2)
One side of the wall, selected by you when you cast this spell, deals 5d8 fire damage to each creature that ends its turn within 10 feet of that side(3) or inside the wall(4). A creature takes the same damage when it enters the wall for the first time on a turn(5) or ends its turn there(6). The other side of the wall deals no damage.
At Higher Levels: When you cast this spell using a spell slot of 5th Level or higher, the damage increases by 1d8 for each slot level above 4th.
(Emphases and numbered notes mine, for reference below.)
Salient features, in the order in which they occur in the text:
Note that 4 and 6 appear to be the same condition due to sloppy writing.
Possible ambiguities are as follows:
What does it mean to "enter" or "be inside" the wall? Does it mean the whole medium-sized creature needs to be inside the wall? I doubt it, because that would intuitively render those parts of the spell inapplicable to creatures of size Medium and up. I know I myself would have a hard time contorting myself into a one foot cross section, to say nothing of the likelihood that I would be so compressed at the random moment in combat when the spell appears. I just don't see that as the intent. It would be much clearer if they said "cross the wall" or "intersect the wall" but I think that is their intent.
How does that Bugbear grapple work, anyway? I think this is a bit of a red herring, though. If the bugbear was not trying to grapple at the beginning of its turn, and you agree with my interpretation, then grappling across counts as "entering" and the bugbear takes damage. Moreover, even if the grapple is broken at the end of the bugbear's turn, that still happens at the end of its turn, which is the same time bugbear should take damage for being inside the wall at the end of its turn. Arguably (although I wouldn't actually argue it, myself) the bugbear might take damage both for initiating the grapple across the wall and ending its turn grappling across the wall.
It surely seems to me that in most situations, the bugbear either enters the wall by virtue of initiating the grapple, or ends its turned having entered the wall by grappling at the end of its turn, and will therefore take damage. And not the Dex-save kind of damage, either.
