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The features bonus for a fighter leveling up to level 5 state that the character is bestowed with an Extra Attack.

Extra Attack states that:

Beginning at 5th level, you can attack twice, instead of once, whenever you take the Attack action on your turn

Does this mean:

  1. I roll a D20 once, if successful, do a damage roll, roll a D20 again, if successful, do another damage roll?
  2. I roll a D20 once, if unsuccessful, I lose the extra attack and my turn ends?
  3. I roll a D20 once, if unsuccessful, I roll a D20 again, if successful do a damage roll, and if unsuccessful then the turn ends?
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    \$\begingroup\$ Option 1 is ambiguous due to use of incorrect punctuation. Can you fix? \$\endgroup\$ – Harper - Reinstate Monica Mar 2 at 19:13
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Options 1 AND 3 are both correct in terms of how this feature works.

The Extra Attack feature simply gives you an extra attack anytime you take the Attack Action. You can take the second attack regardless of whether you hit or miss with the first attack.

Keep in mind that this feature is only available when you take the Attack Action. If you take any other Action, you do NOT then get to make one attack because of this feature. Converserly, you cannot take the Attack Action, and then take a different Action (like Dash, Disengage, etc) instead of your second attack.

Also, it's important to remember that your turn doesn't necessarily end once you take your second attack. The only thing that ends is the Attack Action portion of your turn...you may still have Bonus Actions or Movement available to you depending on what else has happened during your turn.

Finally, both @Medix2 and @JDM7 have brought up excellent points in the comments below: not only can you choose to move between your multiple attacks, you can basically 'trade' one (or more) of your attacks for the ability to do something other than just a normal weapon attack.

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    \$\begingroup\$ Option 3 is correct only if the first swing misses. If the first swing hits, then option 3 would have you quit the turn. But you get another swing, \$\endgroup\$ – Harper - Reinstate Monica Mar 2 at 0:43
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    \$\begingroup\$ @Harper-ReinstateMonica Exactly why I said both were correct. As the options are written, no single scenario accurately covers the entire use case. \$\endgroup\$ – aaron9eee Mar 2 at 6:54
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    \$\begingroup\$ It could be worth adding that you can use either of the attacks to do a special attack action such as grapple, shove, or any special attack action as pointed out in the PHB as well as Basic rules -> Making an Attack -> Melee Attacks dndbeyond.com/sources/basic-rules/combat#MeleeAttacks Internal question around multiple attempts for reference. rpg.stackexchange.com/questions/97646/… \$\endgroup\$ – JDM7 Mar 2 at 9:26
  • \$\begingroup\$ wow, OP is confusingly written for lack of proper punctuation, but yeah, I see it now. \$\endgroup\$ – Harper - Reinstate Monica Mar 2 at 19:11
  • \$\begingroup\$ @JDM7 Good call! I'll work that into my answer. Thanks for the pointer! \$\endgroup\$ – aaron9eee Mar 3 at 7:03
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None of your scenarios are quite correct. The answer to this is found in Chapter 9: Combat of the Player’s Handbook or the Basic Rules, under “Actions In Combat”:

Attack

The most common action to take in combat is the Attack action, whether you are swinging a sword, firing an arrow from a bow, or brawling with your fists.

With this action, you make one melee or ranged attack. See the "Making an Attack" section for the rules that govern attacks.

Certain features, such as the Extra Attack feature of the fighter, allow you to make more than one attack with this action.

The key here is that “taking the Attack action” is different to “making an attack”.

  • Making an attack, as per Chapter 9, means choosing a target, making an attack roll, and if you hit, making a damage roll and dealing damage. (You can also forgo trying to do damage, and use your attack to attempt to grapple or shove your target, which works a little differently.)
  • Taking the Attack action is an action available to all characters that allows them to make an attack in combat. There are other ways to make an attack - opportunity attacks, specific class features, casting certain spells (e.g. booming blade) etc - but this is the basic, universal one.

Extra Attack modifies the Attack action for Fighters (and other classes that receive the feature) so that they make two attacks - i.e. they “make an attack” twice (or more at later levels).

So the correct description in your style is:

  • You make an attack (choose a target; roll a d20 to see if you hit; roll damage if you hit); then if you wish, make another attack (choose a target; roll a d20 to see if you hit; roll damage if you hit).

I’ll also add that taking the Attack action doesn’t automatically end your turn, regardless of how many attacks you get to make. As is the case with most actions, you can also:

  • take one bonus action if you haven’t already, and have a valid one available (two-weapon fighting and some class features, like Flurry of Blows, even require you to take the Attack action before you can use them);
  • do something that doesn’t count as an action (speak briefly, interact with one object, use certain class features etc); and
  • move, if you have movement left (you can even move in between your multiple attacks).
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The first scenario you listed is correct

You choose a target and make an attack roll. If it hits, you roll for damage. Then you may choose another target (the same target or a different one) and make another attack roll. If it hits, you roll for damage. Additionally, you do not have to do two attacks when using the Attack action, you can choose to do only one if you so wish.

The 'Extra Attack' Feature simply allows you to do two attacks (or more as a Fighter levels up) whenever you spend your action on a turn to attack. This means that you make two completely separate attacks, not a single attack that you can roll again on if you miss (thus the third scenario is incorrect). Additionally, the second attack is not influenced by the result of the first attack, and regardless of whether you hit or miss the first attack, you can do the second attack (thus the second scenario is also incorrect).

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    \$\begingroup\$ It may be worth mentioning that you can even move between the two attacks \$\endgroup\$ – Medix2 Mar 1 at 9:00

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