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I have a champion fighter with two scimitars. This fighter took the Two-Weapon Fighting fighting style and often uses both of them for higher damage output. Sometimes in our sessions, I have to make a separate attack roll for both of them, but other times, I just roll one d20 for both.
What is the proper way for making attack rolls with two-weapon fighting?
From the PHB
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.
When you make an attack, your attack roll determines whether the attack hits or misses. To make an attack roll, roll a d20 and add the appropriate modifiers.
Now what it says here is that you make an attack, and use your bonus action to make another attack. So you would roll two attacks one with an action and one with a bonus action. It's a small line of text and it's fairly easy to misinterpret. I hope this helps!
Two-weapon fighting in D&D 5th Edition requires you to
So as a level 1 Fighter, you would make 2 attack rolls, one for the regular Action, one for the Bonus Action. As a level 5 fighter, you'd make 3 attack rolls, 2 for the regular Action, one for the Bonus Action; at level 11, 4 rolls (3 regular, 1 bonus); at level 20, 5 rolls (4 regular, 1 bonus).
Making multiple attack rolls, one for each attack, makes it more likely that at least one of your attacks will connect; consider, for example, a level 4 fighter making 2 attack rolls with this feature. If they've been optimizing for damage output, they'll have a Strength score of 18, making their STR modifier +4. So their +HIT will be a +6, and the damage modifier on their weapon attacks will be +4.
Against an AC16 target, they'll have a 55% chance to hit the target, because they'll be required to roll a 10 or higher on their d20 roll to successfully hit. But because they make two attacks, each attack has its own 55% chance of hitting, and so the chances that at least one roll hits is (1-(1-.55)^2)==0.7975, or a 79.75% chance.
So instead of hitting about half the time in combat, you'll successfully land hits 4/5 times each round when you make individual attack rolls.
Note that this does not affect your average damage; your DPR (Damage Per Round) as a Level 4 Champion Fighter with 18 Strength and two Short Swords against an AC16 target is 8.95DPR, regardless of whether you make two attack rolls, or make one attack roll and use the result for both attacks.
So if your DM were considering adopting a variant rule where you did combine your attack rolls into a single roll for all attacks, I'd advise against it; it doesn't improve your average damage, and makes individual rounds of combat less satisfying.
