epithet
Explorer
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Some questions:
1) If the word "then" was inserted after the comma, would you consider that a timing requirement?
2) If the word "if" was replaced with "after", would you consider that a timing requirement?
3) How does this sentence differ from the 3rd bullet in the feat? It follows the same "If X, Y" format. Does that mean I get to "use your reaction to take no damage if you succeed on the saving throw, interposing your shield between yourself and the source of the effect" as long as at some point on my turn I end up being "subjected to an effect that allows you to make a Dexterity saving throw to take only half damage"?
I searched through the Classes and Combat chapters of the PHB on D&D Beyond, and found exactly zero instances where the word "then" came after the comma in a sentence with the form "If X, Y". If we apply the logic that sentences that take this form have no timing restrictions between X and Y, specifically that Y can happen as long as X eventually happens, the rules start saying some very strange things.
Martial Arts: "if you take the Attack action and attack with a quarterstaff, you can also make an unarmed strike as a bonus action, assuming you haven’t already taken a bonus action this turn". Why can't I do an unarmed strike when I Dash or take some other non-Attack action, because I declare that I'll take the Attack action on some future turn?
Natural Explorer: "If you are traveling alone, you can move stealthily at a normal pace." Why can't I move stealthily at normal pace when I'm traveling with my party, because I declare that I'll travel alone tomorrow?
Ranger's Companion: "If you are incapacitated or absent, the beast acts on its own, focusing on protecting you and itself." Why can't the beast act on its own when I'm conscious, because I declare that I'll knock myself unconscious later tonight?
Stroke of Luck: "if you fail an ability check, you can treat the d20 roll as a 20." Why can't I treat any roll I like as a d20, because I declare that I'll fail an ability check in the future?
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Some answers:
1) Maybe, not necessarily.
2) Yes. "After" establishes a sequence.
3) It doesn't. It means that the triggered condition (take no damage) happens at the same time as the trigger (you are subjected to an effect.) See below.
Your examples are great, thank you. For each of these examples, the "If you ... you can" language is used to refer to a triggered benefit that happens concurrently with the trigger, neither before nor after. Looking at each example in turn shows the consistent concurrence of these circumstances.
Martial Arts: You know that the unarmed strike is concurrent with the Attack Action because the initial statement of the rule uses "when" (When you use the Attack action with an unarmed strike or a monk weapon on your turn,) meaning "at the same time as." Therefore, in the example text "if you take the Attack action and attack with a quarterstaff, you can also make an unarmed strike as a bonus action" it is clearly the case that your bonus action unarmed strike is resolved at the same time as, and therefore as a practical matter as part of, the Attack Action. This makes perfect sense, because we're talking about an attack that does not differ in any way from a regular attack save that it must be an unarmed strike. In other words, your bonus action is consumed to give you an additional Extra Attack.
Natural Explorer: Here is as clear an example as you could ever hope for. "If you are traveling alone, you can move stealthily at a normal pace." The ranger does not complete his travel before he gains the ability to move stealthily at a normal pace, it very obviously must happen at the same time. Trigger and triggered benefit cannot be sequential, they must be concurrent.
Ranger's Companion: This example is different from the others in that it lacks the "you can" language, but it is functionally the same. "If you are incapacitated or absent, your beast companion acts on its own, focusing on protecting you and itself." Clearly, as with the Natural Explorer example, you can't reasonably read this to require that you complete your incapacitation or your period of absence before the companion can act on its own. The companion's independent action must occur during the time that the ranger is incapacitated or gone, not before, not after. Here again, the triggered benefit is concurrent with the trigger.
Stroke of Luck: This rogue benefit must happen in an instant, with the trigger and benefit taking place at exactly the same time for either of the benefits or triggers described in the feature. "If your attack misses a target within range, you can turn the miss into a hit. Alternatively, if you fail an ability check, you can treat the d20 roll as a 20." Notably, though, while the trigger and benefit happen at the same time, the first benefit in particular requires the DM and player to, in essence, go back in time to resolve it. The attack happened, the dice betrayed the rogue, and the result indicated a miss, but the feature allows the rogue to go back and make it a hit, instead.
So, what do these examples tell us about how we should read and adjudicate the "if you ... you can" language of the Shield Master feat? Simply that the shove should be resolved as part of the Attack Action, because the benefit (the extra shove attack) must be resolved at the same time as the trigger (the Attack Action). Like the Martial Arts example, the shove should be treated as another Extra Attack which can only be used for a particular type of attack (in this case, a shove instead of an unarmed strike) which is otherwise exactly like a regular attack made as part of the attack action. The Stroke of Luck feature tells us that for benefits that are resolved concurrently with triggers, we can actually apply the benefit retroactively, so there should be no issue with determining which of the attacks was the "bonus action shove" after the attack itself has already been resolved.
Your excellent examples also demonstrate that Jeremy Crawford is simply incorrect when he suggests that "if you ... you can" always establishes a sequential timing requirement. Clearly no one will be telling the Ranger he needs to do a little hex crawling and finish his trip before he can sneak up behind a foe at a brisk pace. Perhaps the feature could have been called "Walkabout, then Pounce!"
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