Full debug:
hashtags have actions
lp verbose - on
ess debug - on

https://gist.githubusercontent.com/andrewkm/33487d74d04c19bb9edb8e415ee45ffd/raw/ce758158205115538e3a7c9413bb7944c1926761/gistfile1.txt

TL;DR
A user with essentials.fly set to true crossing into a world with essentials.fly set to false will keep their essentials.fly true permission allowing them to fly. Perhaps doesn't change to false fast enough. If the user tries /fly again however, essentials.fly is correctly showing as false.

@lucko perhaps you can shed some light here for us :)

Tested with other world change methods as well to confirm it's not a portal/stargate issue. (Such as force teleporting the user to the essentials.fly false world with multiverse).

Already responded in the Discord, but essentials.fly doesn't control the user's fly toggle itself - it controls whether they can use /fly to toggle flying.

This is essentially a feature request for disabling fly mode when a user teleports to a different world where they don't have the essentials.fly permission, which could be a config option.

Edit: Essentials already does this, but there's some permissions issue with your setup that interferes with this.

Awesome :) would love it if you guys can implement this.

This has fixed the issue @md678685
LuckPerms/LuckPerms@6baa472

If there is still something specific you would like shared from our startup log let me know (I cannot share the full log unfortunately.)

@md678685

Here are the startup logs from when it was broken as it pertains to Essentials and LuckPerms
https://pastebin.com/raw/hBaxqrAR

Do you have a server startup log for this? It seems like EssentialsX isn't properly detecting and using LuckPerms as it should.