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Barbarian Reckless Attack is one of them:

When you make your first attack on your turn, you can decide to attack recklessly...

When exactly "you make your first attack"??

  1. When you declare the attack / target.
  2. Before Rolling the Dice.
  3. After rolling the dice, but before knowing hit / miss.
  4. After deciding hit / miss, before rolling for damage.
  5. After damage is dealt.

P.S.: This is about the wording, not about the barbarian ability. It is included only as an example of the wording appearing in official text.

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    \$\begingroup\$ What is the actual problem you are encountering? It's hard to answer a question about this kind of wording in a completely general way without context. The answer may differ depending on what follows. \$\endgroup\$ – Bloodcinder Jun 7 '18 at 12:37
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    \$\begingroup\$ If this question is not about the specific barbarian ability, but about the 'wording', can you provide any other examples of where this wording is used? That might prevent answers focusing exclusively on a ruling that's only appropriate for this barbarian ability, that wouldn't work when this wording is used elsewhere. \$\endgroup\$ – Tiggerous Jun 7 '18 at 12:49
  • \$\begingroup\$ Can you explain in your question how your plain English reading of the text has been interpreted at your table? I have found, when asking questions, that it is often helpful to provide "this is how I think it works" since that gives the answerers an opening to agree or disagree, and then support why they agree or disagree. \$\endgroup\$ – KorvinStarmast Jun 7 '18 at 12:53
  • \$\begingroup\$ I have an answer for the Barbarian ability, but without other examples my best answer is "it depends on the context". \$\endgroup\$ – goodguy5 Jun 7 '18 at 13:00
  • \$\begingroup\$ I'll close the question until i get home and reach the books. \$\endgroup\$ – Mindwin Jun 7 '18 at 14:08
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You apply effects when the effect tells you to. You decide to apply the effect prior to the attack roll.

The most obvious generic example of an effect being applied when you attack is your proficiency bonus. The section on proficiency bonus and attacking reads (emphasis mine):

You add your proficiency bonus to your attack roll when you attack using a weapon with which you have proficiency...

Now let's ask two questions:

When is this effect applied?

The effect is applied after you have selected a target to attack and after you have rolled, but before you have determined if your attack roll hit. We can tell this because the wording add ... to your attack roll requires that there is already an attack roll to which we then apply the proficiency bonus.

When do you decide to apply the effect?

This is really the core of your question. Looking at the proficiency bonus, you decide to apply the bonus when you select to attack using a weapon with which you are proficient. Since target viability is determined in part by weapon range, weapon selection is done prior to target selection. The timing of picking a weapon and a target is largely academic and can just be bundled into the targeting part of making an attack.

We can also consider when you attack in context with other abilities.

When you attack vs. When you hit

Paladin's Divine Smite reads:

...when you hit a creature with a melee weapon Attack...

Since it does not say when you attack and then apply the effect on hit, we can deduce that there is an intended mechanical difference between when you attack and when you hit. Because hitting is not guaranteed on an attack, but is guaranteed on a hit, this means that effects that say when you attack have some uncertainty on whether they will take effect. This uncertainty is provided by the attack roll. The attack roll is the break point between the certainty of a when you hit and the uncertainty of when you attack. You decide to use the when you hit after the result of the attack roll has been determined and is a hit. Since when you attack must be on the other side of the break point, it must be decided before the attack roll is made.

FenrirG has pointed out that there is a period between the attack roll and determining if it is a hit. I don't think this changes my argument. Unless another feat is applied during that time (a la Lucky), nothing changes in the game state, other than player knowledge. Since player knowledge does not affect the outcome, my previous point stands.

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    \$\begingroup\$ There is a small step between when you attack and when you hit that you might want to add somewhere: after you roll the die, but before the outcome is determined. This wording is used in some features, like the Lucky Feat. \$\endgroup\$ – FenrirG Jun 7 '18 at 13:31
  • \$\begingroup\$ @FenrirG I think I've covered it now. \$\endgroup\$ – A Very Large Bear Jun 7 '18 at 13:38
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Depends on the feature's effect.

Since the timing is not specified, you should note the general timing of the individual effects of features.

For your example, Reckless Attack, the instantaneous effect is getting advantage on attack rolls. So you can declare using this feature after choosing your target but before rolling for the attack. This is when advantage and disadvantage for attacking is normally taken into consideration.

An example for using RA at the last second:

Ulgar the Barbarian wants to strike Monk Disciple

DM: The monk has taken the dodge action last turn so Ulgar attacks with disadvantage.*

Ulgar's Player: I want to use Reckless Attacks feature to gain advantage on my attack rolls.*

DM: Okay the advantage & disadvantage take it each out. Roll single die to attack.

*can swap these two sentences' order and it would still be valid.

If there was a specified timing, it would've been noted on the feature. There are two examples for both before and after seeing the roll:

Lucky Feat

[...]after you roll the die, but before the outcome is determined.

Portent Feature

From Divination Wizard.

You must choose to do so before the roll.

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