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I attack an enemy using a dagger with my right hand, drop it, then grapple the enemy using my right hand (Extra Attack).

Using the Two-Weapon Fighting rule:

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. [...]

because I've attacked with a dagger before, I pull another dagger with my left hand and use it to stab them again.

Will this scenario work?

Note: This is a bit different from Can one attack for damage after having grappled an opponent? because the question is about the off-hand attack.

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No, this won't work exactly the way you describe.

Two-weapon fighting requires two weapons to activate

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.

The rules for Two-Weapon Fighting require you to be holding both weapons at the time you use it. It say you use a weapon that you are holding in the other hand. Not you will be holding. Two-Weapon Fighting requires you to be holding two weapons to use it. It isn't called One-weapon-and-maybe-another-later Fighting for a reason ;).

That means you cannot use Two-Weapon Fighting unless you are holding both daggers at the time of the attack.

This question talks more about this specific issue.

If you start with both daggers in hand it works

If you start with two daggers in hand the order would go like this:

(Which hand you use right/left, doesn't actually matter. 5e does not have the concept of an "offhand". So, you can flip right for left below easily.)

  1. Attack action to do one dagger attack (right hand)
  2. Drop dagger (right hand)
  3. Grapple using Extra Attack (right hand)
  4. Use bonus action to perform TWF attack with other dagger (left hand)

There is no reason you cannot take your bonus action TWF attack after your Extra Attack grapple because the rules say:

You choose when to take a bonus action during your turn, unless the bonus action’s timing is specified...

In fact, this is the default place for the TWF to go. So there's not much to debate here. Regardless, since the TWF attack is a bonus action and the timing is not specified, you can take it any time during your turn.1

Also, since you started with two light melee weapons in your hands you meet the requirements for TWF. It doesn't matter that you drop one subsequently.


1 - It is unclear if you can technically insert the bonus action TWF attack between the 1st and 2nd attacks though according to Jeremy Crawford here. This isn't relevant to this case though. (thanks @V2Blast for pointing this out)

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No, this would not work unless you were holding both daggers to begin with

The issue here is whether you can trigger Two Weapon Fighting if you attack whilst originally only holding one weapon. The accepted answer to this question states that you cannot.

However, if you were to already be holding two weapons, attacked with one and then dropped it to grapple, then you could attack with the other as per TWF, since this would be like having thrown a dagger as the accepted answer referenced above explains, also per this answer to a different question.

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Concerning the question in your title

You definitely can (by RAW)! By raw, there is nothing that prevent a character from attacking with a weapon, grappling an opponent, and attacking the grappled opponent with the TWF-attack. The only restriction being that you need a free hand when you try to grapple.

Although, as a GM, I would personally deny the TWF-attack if you didn't have the weapon in hand at the time of the first attack. But that is just my interpretation of what TWF represents.

Concerning the question in your post

Your scenario is either a GM call or doesn't work as you put it. But not for the reason you think.

The reason I wouldn't allow it is this (from D&DBeyond):

You can also interact with one object or feature of the environment for free, during either your move or your action. For example, you could open a door during your move as you stride toward a foe, or you could draw your weapon as part of the same action you use to attack.

In your case, I would interpret dropping your weapon and drawing a new one as being two separate environmental interaction. This is potentially a GM ruling because there is no rules about specifically dropping a weapon as far as I know.

The reason there might be a GM call is found in these two answers taken from this site. The first asks if dropping a weapon held in hand is free. The accepted answer quotes a tweet from Jeremy Crawford replying that it is not intended as such. The second answer asks about passing a weapon, and the accepted answer makes the point that throwing the weapon takes an interaction and picking it up takes another.

Because those two answers contradict themselves and that the rules as written are unclear. Ask your GM because the rules don't ensure that you can do what you describe.

Or you could have your second dagger in hand at the beginning of your turn and the scenario becomes completely legal by RAW.

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No. Grapple is not "An Attack with a Different Light Weapon"

The provision of TWF is that it allows you to make an attack with a different light weapon in your other hand. Grapple is not an attack with a light weapon. Dropping the weapon before executing the attack aborts the attack with the other light weapon.

TWF does not permit you to make an offhand unarmed attack, cast a cantrip, or other attack like action that is not "an attack with a different light weapon".

If this were the case, it would be stepping on the toes of the Extra Attack class feature.

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    \$\begingroup\$ You've still misunderstood what's going on. Stepping through - the character begins their turn. They take the Attack action, and make one attack with a dagger; as they have Extra Attack, they can also make a second attack in this action, and they choose to drop the dagger and initiate a grapple. They then use a bonus action to make a two-weapon fighting attack using a dagger held in their other hand. \$\endgroup\$ – Carcer Sep 7 '18 at 16:16
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    \$\begingroup\$ First, use action to Attack. First attack will be a right hand dagger attack. Then I drop the dagger on my right hand. My second attack will be a grapple the enemy with right hand. Then I use a bonus action from TWF for my left hand wielding a dagger to stab target. \$\endgroup\$ – Vylix Sep 7 '18 at 16:17

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