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The specific scenario:

I have a fighter character with Quick Draw feat and Sidestep Charge feat, and this fighter charges to a enemy wizard with his longsword two-handed to utilize his 1.5 * STR DMG bonus.

And then, after his charge attack, he switches his longsword to one-handed (IDK what action this is) and draws a whip as a free action (Quick Draw) to prevent this wizard from escaping his AoO via a 5-feet-step. (With a reach weapon, now he can threaten 10 feet.) After doing so, he ends his turn.

But later in the same round, an enemy barbarian charges at this fighter. As a reaction to this attack, the fighter instantly triggers his Sidestep Charge feat and gains +4 dodge AC against this attack. After successfully avoiding this charge, based on the feat's effect, he gains a chance to make an AoO against this barbarian.

To utilize his STR DMG bonus again, he chooses to drop his whip (as a free action), switch his longsword back to two-handed (IDK what action this is) and make his AoO.

And right after this AoO, he draws another whip (as a free action), switches his longsword to one-handed again (IDK what action this is), and regains his threat range.

Are these actions possible? Should I count hand-switching as a free action, just like dropping an item?

PS. Another extreme scenario if it is a free action:

As a fighter with Improved Unarmed Attack and Two-Weapon Fighting feat, I can make a full-round attack with my longsword two-handed as my main attack and my left empty hand as my off-hand attack by constantly switching between one-handed and two-handed between every single attack during my full-attack action.

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    \$\begingroup\$ Probably a minor point, but ranged weapons normally don't threaten an area and can't be used to make attacks of opportunity; to the extent that it matters, should answers assume the fighter has a relevant feat tree for the AoO part? \$\endgroup\$
    – minnmass
    Apr 28, 2023 at 21:45
  • \$\begingroup\$ You don't need switching grips to be a free action to address the PS. The fighter could just use the longsword two-handed and and kick or headbutt ("[A]n unarmed strike… may be a punch, kick, head butt, or other type of attack," says Unarmed Strike (PH 121)). \$\endgroup\$ Apr 28, 2023 at 22:28
  • \$\begingroup\$ @minnmass Thanks for noticing. I just switched the dart to whip. \$\endgroup\$ Apr 28, 2023 at 22:31
  • \$\begingroup\$ @HeyICanChan Oh, that's nice. Then the fighter can actually use a greatsword while still doing two-weapon fighting in this case? I heard people can use their armour spike but didn't hear of using the unarmed attack to do that. As an extension, can a monster (let's say Marilith) use this rule to make additional one unarmed attack (let's say by head butt) in its full-attack action with multiweapon fighting feat? \$\endgroup\$ Apr 28, 2023 at 22:33
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    \$\begingroup\$ @TerryWindwalker The fighter (or marilith) would need the Improved Unarmed Strike feat, of course, but, otherwise, sure. Folks tend to use armor spikes because they're already proficient with them, though. \$\endgroup\$ Apr 29, 2023 at 23:45

1 Answer 1

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Some but not all of those actions are possible.

You can switch from two- to one-handed as a free action.

And then, after his charge attack, he switches his longsword to one-handed (IDK what action this is) and draws a whip as a free action (Quick Draw) to prevent this wizard from escaping his AoO via a 5-feet-step. (With a reach weapon, now he can threaten 10 feet.) After doing so, he ends his turn.

There is no explicit RAW answer for this, but in lieu of any explicit rules, people tend to, as you mentioned, use dropping an item as a justification for going from a two- to one-handed grip as a free action. There was a rules article on the WotC website that has since been deleted quoted here that backs this:

Although the rules don't mention it, letting go of a two-handed weapon with one hand or putting a free hand back on the weapon is a free action for you. Drawing the smaller weapon requires an action, but if you have the Quick Draw feat, it's a free action. Note that you can take a free action only during your turn.

You cannot take a free action outside of your turn.

To utilize his STR DMG bonus again, he chooses to drop his whip (as a free action), switch his longsword back to two-handed (IDK what action this is) and make his AoO.

Let's take a look at that last sentence again:

Note that you can take a free action only during your turn.

There's only one free action you can take outside of your turn:

In general, speaking is a free action that you can perform even when it isn’t your turn.

The exception proves the rule here: unless explicitly stated otherwise, a free action must be taken on your turn. You cannot drop a weapon outside of your turn, nor can you change your grip outside of your turn.

You can switch repeatedly on your turn, with limits.

As a fighter with Improved Unarmed Attack and Two-Weapon Fighting feat, I can make a full-round attack with my longsword two-handed as my main attack and my left empty hand as my off-hand attack by constantly switching between one-handed and two-handed between every single attack during my full-attack action.

Free actions are limited entirely by DM fiat:

Free actions consume a very small amount of time and effort. You can perform one or more free actions while taking another action normally. However, there are reasonable limits on what you can really do for free.

You can switch from two-handing to one-handing, and probably back, and maybe back again, and possibly back again again, but the only line drawn RAW is that there are "reasonable limits." Without a hard rule, you'll need to ask your DM how many free actions to change your grip are reasonable within the span of a turn.

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