Use Giant Fly to drag an enemy over a Bonfire?

I'm still rocking a low level character, so I don't have access to tons of speed or strength. Or spells. And of course, DC checks would be pretty easy to pass. but here we go:

1. Use Find Familiar to summon a Giant Fly before the battle
2. Use Create Bonfire under an enemy that is large or smaller (takes 1d8 fire damage if it fails the DC)
3. Have the Giant Fly grapple the enemy (DC12), lifting and lowering them onto the bonfire repeatedly for up to 25 feet of movement before finally dropping them (5 feet to reach the enemy, half movement while grappling, should give two forced dips into fire plus one drop)
4. Fly is technically outside the 5ft cube of the bonfire the whole time, but the enemy is dangling in it, so the fly doesn't take damage. Enemy takes 3d8 if it fails all of its saves

(With this plan the GM might get rules lawyer-y and say the enemy only takes damage the first time it enters the bonfire space on the Fly's turn. And they may argue that the fly enters the bonfire space the first time to grapple the enemy. But hey, it's got 19HP it can handle it!)

OR

1. Use Find Familiar to summon a Giant Fly before the battle
2. Use Create Bonfire under an enemy that is large or smaller (takes 1d8 fire damage if it fails the DC)
3. Have the Giant Fly grapple the enemy (DC12), lifting them 25 feet into the air before dropping them onto the fire (5 feet to get there, half movement thereafter)
4. Enemy takes 2d6 damage from the fall and hopefully fails their DC to become prone. They take another 1d8 at the start of their turn, then presumably leave the bonfire
5. Fly is still 25ft in the air, outside of melee range; use it to keep attempting to drop or move the enemy on the fire

All of this works even better if another player is able to assist by creating the bonfire for you, or can otherwise disadvantage the enemy

"Any creature in the bonfire’s space when you cast the spell must succeed on a Dexterity saving throw or take 1d8 fire damage. A creature must also make the saving throw when it moves into the bonfire’s space for the first time on a turn or ends its turn there"

Spell description seems to indicate you apply the damage basically once when you first cast the spell, and then once per target's turn.

It is a common tactic to grapple a target and hold them in an aoe while the person doing the grappling is just outaide, so thats pretty standard

This would work much better with Spike Growth as it doesn't have a once per turn limitation.

A familiar can’t attack. A grapple is initiated with an unarmed strike, which is an attack. So, it can’t grapple anyone, because it can’t attack them. 

Quote from Xalthu >>

A familiar can’t attack. A grapple is initiated with an unarmed strike, which is an attack. So, it can’t grapple anyone, because it can’t attack them. 

 Some warlock familiars could still do this.

Quote from Tana___ >>

Quote from Xalthu >>

A familiar can’t attack. A grapple is initiated with an unarmed strike, which is an attack. So, it can’t grapple anyone, because it can’t attack them. 

 Some warlock familiars could still do this.

 If we’re talking about pact of the chain familiars, the ones with a fly speed are size tiny. You can only grapple creatures up to one size larger than you, so in theory, they could grapple a tiny or small creature. There are very few small enemies, but sure, they could try. 
The problem there is, those familiars have a 6 str, so their attack to make the grapple would be at a +0 to hit (pb+2 then str -2). So in theory, there may be some low AC small creatures out there you could try this on, but there are always going to be better options.

Granted, it would be kind of awesome if it worked. But it’s almost never going to work, and certainly not worth the action economy.

Quote from Xalthu >>

A familiar can’t attack. A grapple is initiated with an unarmed strike, which is an attack. So, it can’t grapple anyone, because it can’t attack them. 

 Ah!! I didn’t realize that grapple was considered an attack. Yeah that pretty much kills my idea 😩

I’ll have to think of some other devious tactics. 

A warlock gets access to cool familiars, but also has access to standard familiars.

Okay! New plan. 

A giant fly has a strength of 14. That means it can carry up to 210lbs of stuff (14x15). So it could pick up a suitably sized boulder, log, chest, etc, fly into the air, and drop the item onto an enemy. 60 feet would cause 6d6 damage if they fail the dex save. Grapple doesn’t apply here since it isn’t acting on an unwilling creature. 

Or use a normal familiar with a bag of holding with 500 pounds of boulders

Quote from SunIsGettingRealLow96589 >>

Or use a normal familiar with a bag of holding with 500 pounds of boulders

 A valid plan! I only have one bag of holding right now and it’s holding a lot of my party’s loot, but absolutely a valid play. Though it may need to be a “replicate magic item” bag of holding created by an artificer. That would allow them to dispel the magic instantly, causing all the boulders to appear in a space at once. Otherwise the GM might force the familiar to remove the boulders from the bag one at a time 🤣

Quote from MongooseGef >>

Okay! New plan. 

A giant fly has a strength of 14. That means it can carry up to 210lbs of stuff (14x15). So it could pick up a suitably sized boulder, log, chest, etc, fly into the air, and drop the item onto an enemy. 60 feet would cause 6d6 damage if they fail the dex save. Grapple doesn’t apply here since it isn’t acting on an unwilling creature. 

 A lot of GMs don't like attempts to bypass the restriction against familiars making attacks with such "not technically attack" effects.