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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.

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.

##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 roll20):

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.

##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.

##Concerning the question in your title##

You definately 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 roll20):

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.

##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 roll20):

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.