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So my character is a rogue arcane trickster who just acquired a Helm of Brilliance and a Flying Rapier. According to the Helm:

As long as the helm has at least one fire opal, you can use an action and speak a command word to cause one weapon you are holding to burst into flames. The flames emit bright light in a 10-foot radius and dim light for an additional 10 feet. The flames are harmless to you and the weapon. When you hit with an attack using the blazing weapon, the target takes an extra 1d6 fire damage. The flames last until you use a bonus action to speak the command word again or until you drop or stow the weapon.

And according to the flying rapier:

You can use a bonus action to toss this magic sword into the air and speak the command word. When you do so, the sword begins to hover, flies up to 30 feet, and attacks one creature of your choice within 5 feet of it. The sword uses your attack roll and ability score modifier to damage rolls.

Can I speak the command word, then have it fly and still remain alit? Does throwing it into the air count as dropping it?

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    \$\begingroup\$ I've added the D&D 5e tag since you quoted from the 5e Helm of Brilliance. \$\endgroup\$ Jun 30 at 19:46

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Tossing the sword into the air counts as dropping it for the purposes of Helm of Brilliance. But I'd allow it anyway.

The relevant part of the Helm of Brilliance description is:

The flames last until you use a bonus action to speak the command word again or until you drop or stow the weapon.

The idea here is that if you are no longer holding the sword, the lights go out. If we allow that tossing the sword up word is materially different than tossing it downward, then that just opens us up to all sorts of semantic arguments to be had. "I didn't drop it, I placed it on the table." "I didn't drop it, a Gronk-spiked it." If you let go of the weapon, you have dropped it, and the light from the Helm of Brilliance effect goes out. Since the Dancing Sword effect requires that you toss it, the effects of these magic items do not work together. This ruling is confirmed by an official ruling in the Sage Advice Compendium:

Can I hand a shadow blade to another PC? It only says the blade dissipates as I throw or drop it.

No. The intent is the blade vanishes when you let go of it (that’s one of the meanings of the word “drop”).

This official ruling plainly states that the intent is that letting go of the shadow blade is covered by the word "drop".

That said, this seems like a case where allowing it to work would be an agreeable ruling, citing rule of cool. I don't think it breaks anything is unbalanced in anyway. There shouldn't be any problems with letting these two items work together in this way.

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