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I am a 5th level fighter with an extra attack and I have TWF and the Dual Wielder feat.

In theory, could I use my first two attacks with a greatsword and then make a bonus action attack with a longsword on one turn, without being required to use my bonus action to unsheathe my longsword and waiting for a new turn to attack again?

I read that I would only need two hands to use the greatsword, not just to hold it.

So again, in theory, could I attack twice with a greatsword and use a free action to unsheathe my longsword with the Dual Wielder feat, and use my bonus action to attack with the longsword in one turn?

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You need to be holding both weapons when you Attack in order to use Two-Weapon Fighting - and attacking with a greatsword requires both hands.

You have the Dual Wielder feat, so it doesn't matter that neither weapon is light. So far so good, however:

The Two-Weapon Fighting rules state:

When you take the Attack action and attack with a light melee weapon that you’re holding in one hand, you can use a Bonus Action to attack with a different light melee weapon that you’re holding in the other hand.

There are two problems here.

Firstly, and most simply, when you attack with a greatsword you are not 'holding [it] in one hand' - it's true that you can hold a greatsword in one hand - but not while you're actually attacking.

Two-Handed. This weapon requires two hands when you attack with it. This property is relevant only when you attack with the weapon, not when you simply hold it. PHB

Secondly, while it's not completely explicit, TWF is generally understood to require that you must already be holding both weapons, when you take the Attack action with the first weapon, in order to have the option of Bonus Action attacking with the second weapon. For evidence of consensus on this ruling elsewhere, see these other related questions, here and here.

To attack with your greatsword you need to use both of your hands, not one hand, and you can't be holding your longsword in the 'other hand' while doing it. You therefore don't meet the requirements of the two weapon fighting bonus action.

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You cannot.

From the Player's Handbook (Page 195):

When you take the Attack action and attack with a light melee weapon that you’re holding in one hand, you can use a bonus action to attack with a different light melee weapon that you’re holding in the other hand.

Emphasis mine. You cannot wield a two-handed weapon in one hand, therefore you do not meet the prerequisites for two-weapon fighting. Dual wielder removes the requirements for light weapons, but not this one, so you can't take the action you suggest.

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  • \$\begingroup\$ Don't ask questions in comments. Regardless what you say doesn't work for the reason outlined above. \$\endgroup\$ – AgentPaper Jul 15 at 9:43
  • \$\begingroup\$ Seeing that I'm new to this forum I wish I had any idea of what you were getting at, regardless it was a theory I was asking more experienced players if it was a possibility based on that link I posted above \$\endgroup\$ – CreatonsOfMyOwn Jul 15 at 9:47
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    \$\begingroup\$ I'm confused. Do you accept the answer(s) we've given, or are you still wondering if what you are asking is possible? \$\endgroup\$ – AgentPaper Jul 15 at 9:51
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PHB page 195 - Two-Weapon Fighting:

When you take the Attack action and attack with a light melee weapon that you're holding in one hand, you can use a bonus action to attack with a different light melee weapon that you're holding in the other hand.

PHB page 165 - Dual Wielder - Bullet 2:

You can use two-weapon fighting even when the one-handed melee weapons you are wielding aren't light.

Removing a condition only removes that specific condition, not all the conditions.

So, when you have Dual Wielder, TWF becomes this:

When you take the Attack action and attack with a melee weapon that you're holding in one hand, you can use a bonus action to attack with a different melee weapon that you're holding in the other hand.

The only thing that changes is that the two instances of the word "light" are removed. Nothing more!

Also, contractions, I think, introduce needless confusion, "You're" means "you are" (indicating being) and does not mean "your" (indicating possession). I've seen too much confusion about such things, to be convinced that when thinking about rules it helps to avoid contractions.

So, removing the contractions:

TWF (with DW):

When you take the Attack action and attack with a melee weapon that you are holding in one hand, you can use a bonus action to attack with a different melee weapon that you are holding in the other hand.

Emphasis mine. The simultaneity of needing to hold both weapons at the same time seems pretty clear here. For example, the text is definitely not like this:

TWF (with DW):

When you take the Attack action and attack with a melee weapon that you are holding in one hand, before the end of your turn you can use a bonus action to attack with a different melee weapon that you will be holding in the other hand that turn.

Also, you need definitely to attack with the 1st weapon, not merely hold it in one hand. So what you ask is not possible as per RAW (but of course a DM might allow or not allow whatever he wants).

The text could have been made more confusion-proof if it had been written like this:

TWF:

When you take the Attack action and attack with a one-handed light melee weapon that you are holding in one hand while also holding a different one-handed light melee weapon in your other hand, you can use a bonus action to make an attack with the second weapon.

Sure, some might argue that interpreting the rule liberally should be allowed. In that case, why not go all the way, right?

TWF:

When you take the Attack action and attack with a light melee weapon that you're holding in one hand, you can use a bonus action to attack with a different light melee weapon that you're holding in the other hand.

Hey, it is not "your" other hand, it is written "the" other hand! So TWF says that I can attack with a different light weapon that my friend Bob is holding in his other hand! Mmm... most DMs would say a definite no.

We can see that "liberal" interpretation or rules can easily lead to nonsense. So, RAW interpretation of rules should only take into account the strictest possible sense of the several potential meanings, and checking the entire rule as a whole not part by part as if they were somehow separated in time. So, the moment you're attacking with the 1st weapon, and the moment considered for the condition of being able to attack with 2nd weapon, are to be the same moment, because it is the same "global condition" i.e. looking the entire rule as a whole, not as a sequence of separate steps.

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