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If an enemy is knocked prone and then grappled by an aarakocra or a PC with the fly spell effect, does the prone effect of the target continue into the flight?

I can't think of a way that the condition would remain, but I really want it to. I appreciate answers based on the 5e rules as written or logic derived from them.

For more context:

I'm trying to make an unorthodox wizard build in 5e. I'm going to make a utility caster that has a low int because no utility or buff spell I know scales with Int. I'm trying to find ways to use a high Strength and buffs to make the build have near-unavoidable damage. The easiest way to do this in 5e is to trigger fall damage; few things can make saves against it, and there is no roll except to avoid or escape the grapple. With enlarge/reduce, I could get advantage on my roll or impose disadvantage on their roll then deal damage. I know that this is ineffective and may not scale well but I still want to try.

Knocking an enemy prone and flying would give disadvantage on their attack roll, which would help me keep concentration and keep my advantage or their disadvantage from enlarge/reduce. Hence why I might use an aarakocra.

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  • \$\begingroup\$ I've edited your clarifications from your comments about the context into your post. \$\endgroup\$ – V2Blast Jul 24 at 6:03
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Yes, they remain prone

RAW

The prone condition ends when the creature spends half its movement to end it. Moving the grappled creature (using any form of movement) doesn't do that.

Prone doesn't necessarily mean prone as in prostrate

Think of the prone condition as being off-balance, disorientated, tangled up or otherwise unable to move normally until you spend some time to recover rather than necessarily lying down.

For a grappled creature, they have no movement so cannot recover. Think of that as the grappler having them in a hold that restricts them physically or would make movement too painful or whatever fits with your visualization of the situation.

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