So after 2 shrouds the target grants combat advantage to just the assassin.
And if you have all 4 shrouds on something for the purpose of the attack in which you invoke your shrouds the target is considered helpless
The majority of the Assassins I've seen played just shroud and invoke (if they hit, they deal damage comparable to a vanilla rogue's SA, if they miss, then Meh) and, once per encounter, stack two shrouds with Kiler's Insight and get to deal 1d6 on a miss.
They will also have Targetted for Death (Lvl 1 Daily) so they can start dealing that 1d6 on a miss each round (or 2d6 each round with a hit) one encounter per day.
If you want shroud stacking incentives, take the at-will that lets you deal slightly more damage per shroud as long as you didn't invoke the shrouds.
The Assassin is fine otherwise (though it could make do with a slight bump to hit points, I'm not too concerned about that since a good assassin will not be easy to target and/or hit. 
Although, I wouldn't mind a feat that increased the die size of Assassin's Shroud.
Something like this:
Empowered Shrouds
Benefit: When you invoke your shrouds, the die size for each shroud increases based on the number of shrouds invoked. For one shroud, the die size is 1d10. For two shrouds, the die size is 2d4. For three shrouds, the die size is 1d8. For four shrouds, the die size is unchanged.
And if you have all 4 shrouds on something for the purpose of the attack in which you invoke your shrouds the target is considered helpless
This is just brutal. You realise this means that the Assassin can use Coupe de Grace against enemies in the middle of combat right?
Especially when you add in the "start stacking shrouds before combat begins" so that they can open each combat with a Coupe de Grace. With a Vicious Fullsword...
I don't know much about the Assassin but anything that can give it access to the Helpless state so easily should be very carefully considered.
There are only 3 PCs in this campaign (2 if you take my defender out), and I haven't really adjusted encounters so far. If we have another PC or 2 join the game permanently, then I may reign in the shrouds. So far though, I'm not seeing a problem.
The only necessary changes for Shroud are for it to 1. only dispel on a miss and 2. have Hidden Insight built into its basic features, with the Hidden Insight feat instead making people unaware you're shrouding them at all.
Only dispel on a hit, surely? Since if you do it on a miss you double-penalise the Assassin character for missing . . . or double-benefit them from hitting if you prefer to see it that way . . . but in any case losing the shrouds on a miss but not a hit makes hit/miss more diverse and the impact of the character on combat more random/swingy.
Only dispel on a hit, surely? Since if you do it on a miss you double-penalise the Assassin character for missing . . . or double-benefit them from hitting if you prefer to see it that way . . . but in any case losing the shrouds on a miss but not a hit makes hit/miss more diverse and the impact of the character on combat more random/swingy.
All striker damage mechanics 'double-penalize', as you say, for missing. Sneak attack, hunters quarry etc all do nothing on a miss, don't see why the assassin should be different.
All striker damage mechanics 'double-penalize', as you say, for missing. Sneak attack, hunters quarry etc all do nothing on a miss, don't see why the assassin should be different.
Except Oath of Emnity, of course, which functions to negate misses.
I never said all striker mechanics did damage on a hit, just that apart from the Assassin none of them did anything on a miss. Yes, O of E does function to increase the chances of hitting which in turn increase average damage but it does as little as all the other striker mechanics if you roll snake eyes.
My point was just that adjusting shrouds in the way you suggested brings the assassin striker mechanic more in line with other strikers, not less. (In case I'm not being clear here I like the idea a lot though I do have some questions about how shrouding multiple targets would work, it seems to me like it could get quite confusing remembering what shrouds are where)
So after 2 shrouds the target grants combat advantage to just the assassin.
And if you have all 4 shrouds on something for the purpose of the attack in which you invoke your shrouds the target is considered helpless
For what it's worth, despite the rest of the discussion, I actually like your original idea a lot. I'm not adverse to assassins wielding the Helpless condition every few turns. Instant death may need to be withheld, but that's doable. Instead of treating them as helpless, you could just say that [Edit:] a successful attack is automatically a critical hit when invoking 4 shrouds, or something.
You can't shroud more than one target. Never have been able to and that wouldn't change here. The fact that you lose shrouds if your target dies from someone else's attack (usually cited as one of their core issues) is already addressed by the fact that you aren't punished for invoking immediately. That's why I settled on my fix idea out of a decent set of options, it addresses all their typical combat problems in one simple point. (Change 2 is just for thematic reasons.)
The OP's "targets under X shrouds grant CA" idea isn't a bad one, incidentally, but it's a nice feat idea, it doesn't address the core problem with the feature.
Oh, that makes a lot more sense then, I thought you meant that shrouds stay on any target you place them on until you miss that target. In that case I think you're spot on.
The one thing that always bugged me about the shroud mechanic was that the damage on a miss part works to increase average damage output over a long period of time which doesn't seem to fit with the assassin thematically, I would have personally thought they should be king of nova damage. When I first read the shroud fluff I thought it would be appropriate to have the shrouds increased on a target anytime they hit or miss you as a class feature, the idea being the more they fight you the better you get at killing them. Or you could have shrouds automatically do max damage to bloodied targets or auto slay targets below 10 hp if you invoke your shrouds on them or a feat to increase shroud dmg die to D8 or a combination of these and many other ideas. I guess the point is that we all think there are improvements that could be made. The question for me is will Wizards make any?
Adding a shroud whenever the target misses you is actually a really interesting idea. Assassins currently have all these ways to get concealment and stealth, but it doesn't really do all that much for them. If they got to add shrouds when they were missed by attacks, it would encourage them to stealth it up right in their enemies' faces.
I think the wording would be something like this: "Whenever an enemy subjected to at least one of your shrouds misses you with an attack you may add an additional shroud as a free action."
I like shroud persisting unless you miss the target. I would take it a step further so on a miss the assasin can choose to use the throuds to do damage and lose all shrouds on target or choose to swimply miss and keep the shrouds on target. In my game the only person who plays a assasin loves daggers so uses only them wich realy means she does not keep up in damage so this would help a lot dps wise. Would change the tactic curently she shouds 1 target while killing the other then moves to the target with 4 shrouds and starts shrouding a difrent one. if shrouds stayed on a hit then she could actualy effectivly shroud the target she wants to kill
If we're going to be all precise about it, I think I'd add "once per round" to that so the combos don't get out of hand.
I'm not really familiar with what combos might be possible but as far as I can see the most powerful situation would be that you put 1 shroud on a target then somehow the target misses you 3 times in one turn to add 3 more. You can't use the power to start shrouding a new target and you can't shroud more than one target at a time so for me it feels like once per round would be an unnecessary complication. Am I missing some devastatingly overpowered exploit?
so other night I let the assasins only lose there shrouds when they missed (they have option of declaring before the attack that there not using there shrouds so they can safely build them up) worked out great the assasin was finaly doing damage comparable to the other striker, lol and the defender for that matter. before the assasin was doing the same damage as the controler much less reliably to. So this option worked great and has found a perminent place in my games.
Free action-at will- once per round
Place a shroud on a target you can see.
Hit: when you hit a target with shrouds on it you do 1d6 extra damage per shroud on the target.
Miss: when you use your shrouds and miss the target you lose all shrouds on target and do 1d6 per shroud on the target after the first one. EX 3 shrouds is 2d6 1 shroud is 0d6
Special: If you are hidden when you place a shroud on the target, the target is unaware of the shroud.
Special: You may choose not to use your shrouds fo ra attack. if doing so it must be announced before the attack roll is made.
Well m sure it could be worded better but thats the basics of how we are using it.
Level 1: 1d6 per shroud.
Level 2: 2d6 per shroud.
Level 3: 3d6 per shroud.
None of that 1d6+3/6 crap. And then use your feat to up those d6s to d8s. I think that's part of the reason that the assassin falls behind once they hit paragon, because of the RETARDED scaling of the shroud damage. This leaves the shrouds comparable to Hunter's Quarry or Warlock's Curse. If you think 12d6 per 4 rounds at epic is overpowered, let me remind you that the Quarry and Curse give exactly that many dice, let alone the bloody Rogue's Sneak Attack, throwing around 20d6 in that time.
This alone, however, gives no incentive to actually stack the shrouds, which is why the OP's idea seems good, maybe not helpless or auto-crit, but maybe increased crit range. As far as I know, no class actually gains an increased crit range at heroic, so that seems like an interesting striker feature to me. The assassin seems like the kind of class that likes to save up for one huge burst of damage, so I think that would fit in rather well.
And if anyone brings up the "1d6+3/6 is only missing out on 0.5 average damage per tier" argument, obviously doesn't get the fact that it's average damage. What happens when you crit? Max damage on an epic shroud would be 12 damage the old way, whereas this way you get max 18 damage. I know it doesn't seem like a lot, but 6 extra damage per shroud, even more if you take the "d8 on a shroud" feat, (which you should) adds up. Does the rogue get a piddly 21 max damage on a crit with sneak attack? No! He gets a freaking 30, even more with backstabber, and it should be so for the assassin too.
Anyways, to end my rant, I'm going to come up with a couple of fixes to the assassin, namely the shroud fix I've proposed here and a few new guild training option, which I will post in its own thread at a later date.
Round 1: 1 shroud = 1d6 extra damage.
Round 2: 2 shrouds = 2d6 extra damage.
Round 3: 3 shrouds = 3d6 extra damage.
Round 4: 4 shrouds = 4d6 extra damage.
Round 5: 4 shrouds = 4d6 extra damage.
Etc.
That right there would make the ranger cry, at least at heroic. We're looking to fix the assassin, not turn it into the unholy lovechild of Artemis Entreri and Drizzt Do'Urden.
EDIT: On second thought, I take that back. In my mind, the most damaging class SHOULD be the assassin (come on, the name implies it), or at least it should rival the Ranger. Unfortunately, the ranger has many, many, many, MANY multi-attack powers. As such, it allows rangers to take advantage of things like Permafrost and other such combos to maximize damage. But that's ok, multi-attacks are the ranger's schtick. Just ask Drizzt Do'Urden. Of course, that might be a bad example, because Artemis Entreri fights with almost the exact same style as Drizzt. Hmm.
The archetypical assassin, on the other hand, should have the ability to pick a guy and say, "You're dead." As such, the assassin should have an unrivaled spike damage. Once again, however, the ranger has stolen that spotlight with his multi-attacks. And since WotC don't seem to want instakills in 4e, there seems to be no good way to do this. That leaves us with some sort of crit mechanic, on top of the shroud mechanic. Or maybe keying off of the shroud mechanic. Essentially something that says, "You're dead." without becoming overtly ranger-like, or, in other words, broken.
In other news, I'm sad to see even my Executioner is behind the party Rogue. Then again, we play with a DM that lets anyone make an extra MBA at the cost of a -5 penalty to both attacks, unless they have the Two Weapon Fighting feat. And he's rolling d8s with kukris somehow (not oversized, he's a halfling), the DM gives him an increased crit range with the kukris, and on top of that, now he's a daggermaster, which means he crits on 17 - 20. He also gets an extra +2 to hit with kukri's instead of the rogue's normal +1, and he has free proficiency with the kukris. He claims that the DM gave it to him. I think he may have misread the part that says shurikens get a damage die increase and thought that it applied to daggers too, and, consequently, kukris. And he also claims that he got the free proficiency with kukris because he's proficient with daggers. I don't think he really understands it, he's just looking for free damage boosts.
I apologize for that last part, it was kind of off topic. I guess I just needed to vent.