In this evaluation of the Assassin's Shroud power, I will demonstrate how, through the wording of the power, damage is produced in possibly unexpected ways. I will also explore issued in timing with shroud invocation and vanishing.
The Mechanic of Assassin's Shroud
Before you make an attack roll against the target, you choose to invoke either all your shrouds on it or none of them. If you invoke your shrouds, the attack deals 1d6 damage per shroud, minus one shroud if the attack misses, and all your shrouds then vanish from the target. This damage roll never benefits from bonuses to damage rolls, and is in addition to the attack’s damage, if any.
Without any beating around the bush, I would like to re-articulate the power in the following manner: each time you make an attack roll, you may invoke your shrouds, which deal full damage as long as you do not miss (and deal partial damage if you do). Your shrouds vanish after damage is dealt.
Attack Rolls, Attacks, and "Then"
Now, of course, we have a classic issue of what an "attack" is, since the damage must be applied to "the attack." But since I cannot resolve that meaningfully, I will defer to convention here. "The attack" will refer to the resulting hit or miss of the corresponding attack roll, or rather the process thereof.
Since shrouds "then vanish" only after "the attack deals ... damage," let us note any situation in which you make multiple attack rolls before the "attack deals ... damage." Let us assume, for simplicity, two rolls are made.
For any given attack using two rolls, shrouds may be invoked twice. The process for damage is a little less clear:
Since they deal the damage and then vanish, we may have the following situations:
- Shrouds deal damage, shrouds deal damage, shrouds vanish; shrouds vanish or attempt to vanish but have already vanished.
- Shrouds deal damage, vanish; shrouds deal damage and vanish or attempt to vanish but have already vanished.
- Shrouds deal damage, vanish; shrouds attempt to deal damage but cannot because they have vanished, attempt to vanish but have already vanished.
- For this interpretation, it is worthwhile perhaps to debate what it means for shrouds to vanish. The power itself never specifies what vanishing truly entails or specifies that a shroud that has vanished cannot have its damage applied. Moreover, since "the attack deals" the damage (as per the power's description) as a consequence of invoking the shrouds, and since the vanishing is a subsequent event, and at least given our order of causality, the damage cannot be dependent on the vanishing occurring. One could argue it is at least dependent on the vanishing not occurring by saying it is dependent on the presence of the shrouds, but this is not written explicitly anywhere (the case against it being, as I have laid out, that the consequence is from the invocation). Still, as it is less vague, we may suppose the whole circumstance fizzles here.
But as stopping here leaves the other path unexplored, I will explore it at least for thoroughness if not for application:
Multiple Invocations, How Many Attacks?
As at least seems reasonable, above I have stated that "the attack" (which deals the damage) should be the one corresponding to the attack roll.
So, let us consider a power with multiple attacks: Twin Strike. If the attack rolls are made simultaneously, any of the possibilities outlined above might occur. If they are made sequentially, it is inarguable that the shrouds have vanished before they can be invoked again. This, at least, seems to be a sensible interpretation: even if the attack can deal damage on a shroud invoked and since vanished, you cannot invoke what is not there. Thus, for any power with secondary or tertiary attacks, or which uses "then" to indicate sequence, or which uses an Effect that occurs after the Hit or Miss of an attack roll (such as Hurricane of Blades, post-errata), shrouds cannot apply their damage (or be invoked, for it to be possible) multiple times. The only minor exception is for any character who can cause shrouds not to vanish. In such a case, damage might be applied on each attack roll; but it still stands to reason, with rare exception*, that the damage applies at most once per roll.
*A debatable exception, and one which I will treat thoroughly later, is for Oath of Enmity or similar multiple-roll mechanics.
One Attack, Many Rolls
There are some powers which exist, at least four from memory, three I recall by name, level, and class of origin, which use multiple attack rolls which "resolve" as a single hit: Shadow Darts, Flurry of Talons, and Shadow Fire.
Since the resolution of these powers is explicitly a simultaneous occurrence, the shroud damage must follow the first possibility outlined above. Thus, for each of these powers, shrouds can be invoked three times. As an example, a single shroud might be invoked three times to deal 3d6 extra damage at level 1 with Shadow Darts.
One Attack, Many Hits
While three applications of a shroud is nice, especially on three different encounter powers, there is at least one circumstance in which powers with multiple hits are already superior: there is a power that hits four times. (There are also several Wizard powers, such as Orbmaster's Prismatic Sphere and Prismatic Wall, that hit three times, against Fortitude, Reflex, and Will, and a few powers scattered throughout other classes and paragon paths which hit two or three defenses.) Since the same attack is applied against multiple defenses and may hit multiple times, and since there does not seem to be sense in saying that there is a set sequence to which defenses to check first (which might cause the shrouds to vanish and thus forgo their damage in some interpretations), shrouds can deal their damage on four hits.
However, from a practical standpoint, this one power applying them four times is not itself convincing. It is a daily power (Every Trick in the Book), for instance; and there is only one of it. (Even most of the 3-defense powers are dailies.) But these multiple-hit powers offer another advantage: multiple damage rolls. Since the three powers given above use a single hit and single damage roll, other modifiers to damage can only be applied once. While Assassin's Shroud can be made to be powerful on its own (particularly at four shrouds), other modifiers are not to be underestimated. But it is good to see that the shroud mechanic combines favorably with these powers as a complement.
Other Circumstances, Many Rolls
Perhaps the whole reason this idea seemed to me not just entertaining, but mind-blowingly powerful was a recent addition to the rules: the alternative reward, Five Stars, Five Strikes
But there are still a few hurdles we must cross before looking at Five Stars, Five Strikes.
Oath of Enmity demonstrates a way to gain additional attack rolls. As I assert in my examination
of Oath of Enmity's mechanics, Oath of Enmity is additive. However, additive or not, it provides us an interesting glimpse into the Assassin's Shroud power:
First, the shrouds may be invoked twice (once for each roll afforded by Oath of Enmity). Whether taken additively or in a multiplicative fashion, the roll for Oath of Enmity that is "use[d]" will determine whether the shrouds deal full or partial damage as the "use" of the roll is in its application against the defense, in evaluating a hit or miss. Thus, Oath of Enmity contributes extra invocations of assassin's shroud.
Five Stars, Five Strikes is worth more consideration, however, as, while it does hit or miss (four simultaneous times), it is separate from the other attack rolls of the power it is used to complement. Because of this, I cannot say with total certainty how it combines with Assassin's Shroud, only offer my best conjecture and hope that whoever may be reading this considers that helpful.
The power consumes a Move Action and establishing a condition which acts as a No Action that may occur in the future. To wit:
If your next melee attack this turn hits, roll four extra attack rolls (using the same modifier as the initial attack roll) and deal 1d8 extra damage to the creature you hit for each of the extra attack rolls that hits.
Since FSFS (for space and ease of repetition) causes another attack to deal extra damage, it itself does not deal damage. However, Assassin's Shroud notes that is is "in addition to the attack’s damage, if any." While some will argue that "if any" here means that for any attack that does not deal damage, the shrouds do not add damage (since the "if" condition is not met); I will assert, as I believe is more logical given English syntax, that "if any" is not creating an if-and-only-if condition, and is rather stating that the damage is not "in addition" but rather on its own in cases without "any" damage onto which to be added.
Since this condition does not require an action - though this may seem silly and is worth its own discussion - you can use multiple FSFSs. (The discussion would concern itself with the item-like nature of alternative rewards and the distinct lack of a note that a character cannot have the same alternative reward twice at once, at odds with the flavor and thus possibly the intention of such rewards, specifically grandmaster training in contrast to boons.) I will not belabor this point, but I will draw some brief conclusions later from the premise of multiple FSFSs.
So, with FSFS, we can add four additional rolls, thus invoking shrouds four additional times and so dealing their damage that many more times.
In addition to the point of debate that is "if any," there is perhaps a larger point of debate: how this extra damage operates. I will note, and subsequently explain, that whichever way it works of the two I will present momentarily, that FSFS does work with Assassin's Shroud, but one route is open to much greater potential.
Namely, these two possibilities are that the extra damage is simultaneous with the complemented attack's damage; and that it is not, that it is an after-effect. While it is "extra damage," and that might naturally incline us to believe it is simultaneous - and while that would be a more favorable interpretation for potential - there is precedence for the opposing possibility.
Swift Bite, a paragon feat from Dragon 367 allows for an "extra 1d6 + Strength modifier damage" "[w]hen you bloody a foe." Since you cannot simultaneously bloody a foe with damage already dealt and add to that damage before it is dealt, this is evidence of "extra ... damage" being dealt separately.
Thus, if it is dealt separately, while all FSFS triggers should occur simultaneously (and thus not compete for damage timing in some interpretations of Assassin's Shroud), it will still occur separately from the complemented power. As a consequence of this, for maximization of Assassin's Shroud, it is better to invoke shrouds on FSFS(s) than it is on any power, as no power allows for more than 4 simultaneous attack rolls against the target of your Assassin's Shroud, with minor exception: Flurry of Talons or Shadow Fire with Oath of Enmity (five or six rolls, depending on your interpretation).
Combining Rolls and Hits
In conclusion, in addition to dealing shroud damage multiple times from multiple roll mechanics and from multiple hit powers, these effects can be multiplied by combining them: for instance, using FSFS on Prismatic Strike (each is or uses, conveniently, an encounter power), to invoke shrouds (at least) four times, and to apply them three times per invocation.
To demonstrate, let us assume Epic tier, the Lethal Shroud feat and four shrouds. A single invocation accounts for 4d8+40 damage. Four invocations produce 16d8+160 damage, and applying them all three times gives us 48d8+480 damage. With additional FSFSs or the use of the 4-hit Every Trick in the Book, and especially if assuming simultaneous resolution with the complemented power, damage can easily reach several thousand if done properly (synergistic Epic Destiny, item selection, and such). Additionally, if the damage is not simultaneous, then it must be separate from the power's damage (rather than a lump sum), which closes off some potential (invoking shrouds on the power itself), yet opens others: vulnerability. While the shroud and FSFS damage is untyped, vulnerability to all damage would still apply.