How do you handle Rogue (Assassins)?

We played it that Assassin gets "assassinate" shot. One attack only if HE surprises the target. That is if his presence was not known to the target.

It could already be in 2nd or 3rd round if Assassin was succesfully hidden until then and wasn't attacking anybody.

One attack with advatage and autocrit if it hits is hardly game breaking.
 

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Okay, so let me collect my thoughts on this.

So I think that this "Surprise" ability is something that happens very rarely. Normally it requires ALL party members to succeed their stealth roll, plus the rogue rolling higher initiative than the enemy.

So yeah I see that the rogue could be like "Well then, I go ahead and play separate from the others."

Anyway, what I personally do here is the following:

1. I tell my players that they can only hide from something if they know it's there. So during normal gameplay there isn't any reason to split up at all.

2. This is mostly depending on context, but combat could happen in three ways. The group gets surprised by something they haven't been aware. Two opposing groups run directly into each other without being aware of each others presence, so nobody gets a chance to surprise. And finally, the I tell the adventurers about a threat they notice and ask them how they want to proceed. Only in this last case, surprise matters at all.

3. So for the case the adventurers are a aware of a threat: What I personally allow is that my players can opt to stay out of combat the first round. If they opt out, they don't need to do a stealth roll (they basically automatically succeed), but in exchange are also not allowed to do any offensive actions in round 1. At the end of round 1 they can get in position and join battle for round 2.

This allows for a lot of versatility, but the rogue never has to go lone wolf mode. In fact in my group it's usually not only the rogue going alone but depending on situation, others want to try surprise as well. Sometimes only the ones in heavy armor pass. Sometimes they don't even try to be stealthy because it seems more reasonable to have the tank charge in first.
 

The assassin's Assassinate ability is somewhat circumstantial. As with any other circumstantial primary character ability, to get it to work properly a DM should be creating/planning/including opportunities for an assassin to use it. Don't spoonfeed the players or telegraph too much, but make sure the players can use their abilities if they apply themselves. Any DM worth their salt should be doing this ANYWAY for all characters. Some tips for the subclass:

1) Make scouting quick and painless for the other players. Don't involve more than a roll or two to set up. Don't use or allow PCs to get away with extended scouting scenes while the others sit twiddling their thumbs.

2) Not all PCs/foes need to be surprised or unsurprised in any particular combat; this can be employed to keep surprise useful but stop it from ruining entire encounters. In games I run, PCs generally have the option of scouting ahead or staying back. Those who stay back don't need to make stealth checks (or have an easier time concealing themselves) and are rarely vulnerable in the first round of attacks but start out surprised. Some enemy groups might employ more alert sentries (adv. on perception checks and thus +5 to passive perception) or be composed of different creature types with different perceptual abilities, making it trickier to surprise ALL of the enemies. One classic example - group of hostile sentients with a guard dog or other monster.

3) Consider non-stealth uses of the assassinate ability. The occasional social encounter helps break up the monotony of a dungeon. Perhaps some percentage of the foes in a hostile area don't automatically recognize the PCs as intruders (provided they don't look too outlandish). Particularly if proper disguise is involved. Consider allowing characters to use deception, disguise, or sleight of hand to set up surprise in some cases. Again, the most important thing is not to make this too long or painful for players who are not involved.

4) Include the occasional venomous monster or harvestable poisonous plant to allow use of Poisoner's kit proficiency.

5) Infiltration Expertise / Impostor may take a little more consideration (as a DM) to make worthwhile. False identities might potentially be used to scout out particular places and organizations during downtime (to keep from taking too much play time away from non-participants); to facilitate safe scouting in a dungeon or enemy stronghold if created beforehand; or to avoid repercussions and consequences in some cases - members of the watch trying to bring the respective PC to justice for past crimes, thieves trying to steal a particular item the PC is known to possess, bounty hunters / assassins hired to capture or kill the PC.
 
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I'm not thrilled with some of the, "Make scouting quick and easy" ideas being discussed. That's an important part of the game for most parties (aka exploration). Nor do I think the assassin is entitled to an Assassinate unless it's well set up, either. That may not happen all that often.

Depending on the group, this is a bit of a hard nut to crack. My tendency is to keep the rules the same and let the group decide how they want to play it. If they're happy with the rogue ranging out front and setting these things up all the time, that's fine. If they want a change they can discuss it with the assassin.
 

Well, you asked how I'd handle it at my table.

I think you're problem is mostly of your own making. It sounds like you're spending too much focus on the rogues solo actions at a time.
The answer is not keeping all the characters together. It's finding that happy medium where you can switch back & forth between rogue/others and leaving everyone feeling involved. Do that & you won't need to modify any rules.

If my answer to your post came off as dismissive - I apologize. That was not my intent.
 

If you want to introduce more situations where the party surprises the monsters, do it.

Surprise happens whenever the enemy doesn't notice a threat, not based on dice rolls.

The party's just talking when suddenly the rogue attacked? They didn't notice they were a threat until combat started, Surprised!

The party kicks down the door to a room without being detected before that? Surprised!

Edit: Here, I'll go over it in detail.

The GM determines who might be surprised. If neither side tries to be stealthy, they automatically notice each other. Otherwise, the GM compares the Dexterity (Stealth) checks of anyone Hiding with the passive Wisdom (Perception) score of each creature on the opposing side.
This? This here determines whether entities notice each other. Nothing more.
Any character or monster that doesn’t notice a threat is surprised at the start of the encounter.
This bit here, however, requires that the noticed entity be identified as a threat.
 
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But that makes the Assassin one of the worst subclasses in the entire PHB, maybe the entire game.

If Assassinate can never happen because it is too hard, too cumbersome to pull off or too risky for the Rogue to even try, then its a useless ability. Infiltration Expertise and Impostor are some of the most Fluff, campaign/DM dependent material in all of 5e. And the Level 17 feature, Death Strike, requires the exact same impossible conditions as Assassinate does.

Two features that will never work and two features that are pretty useless means you may as well take no Rogue subclass over taking Assassin. Which, to me, says Assassin needs the fix, not the game's rules.

I like to compare it directly to the same feature of the other subclass. I've played a Rogue who took Thief as their subclass and I haven't used their feature even once. I suspect both features are meant to be extremely specialized skills for very specific situations.

Both of them HAVE a use, but they may only work every once in a while. If your entire party happens to roll well, you get a really awesome ability.

Besides, I didn't suggest any game rules changes. That's the way they are currently worded.
 

But that makes the Assassin one of the worst subclasses in the entire PHB, maybe the entire game.

If Assassinate can never happen because it is too hard, too cumbersome to pull off or too risky for the Rogue to even try, then its a useless ability. Infiltration Expertise and Impostor are some of the most Fluff, campaign/DM dependent material in all of 5e. And the Level 17 feature, Death Strike, requires the exact same impossible conditions as Assassinate does.

Two features that will never work and two features that are pretty useless means you may as well take no Rogue subclass over taking Assassin. Which, to me, says Assassin needs the fix, not the game's rules.
Did... did you miss the part where you get advantage on outspeed enemies regardless of surprise?
 

This bit here, however, requires that the noticed entity be identified as a threat.

No it doesn't. It requires the person BE a threat and be noticed.

I've said in the past, the spirit of the rule appears to be that you see something dangerous at least half a second before it hits you. If so, you aren't surprised as there's time to dodge out of the way.

If you are talking to someone and they suddenly pull out a weapon, you have the time required to pull out the weapon, get into a fighting stance, close the distance to you and attack in order to react. You aren't surprised. Even if they have the weapon in their hand, you still have the time required to get into a fighting stance and swing the weapon.

From my view of the rules, this is the difference between surprised and not surprised:

Surprised - I'm walking through the market buying apples. Suddenly there is a pain in my side. I look down and there is a crossbow bolt sticking out of me. I look up and I see a guy in a cloak hiding behind a nearby stall holding a crossbow and pointing it at me.

Not Surprised - I'm walking through the market buying apples when I notice someone hiding behind a stall pointing a crossbow at me, his finger on the trigger ready to fire. I still have half a second to react. If I react quick enough I can still get over to him and attack before he presses the trigger. Now we determine who reacts faster by rolling initiative.

The key is that if you are able to see the person when he starts the attack, you have time to react to it before it finishes. Which is why, in some rare circumstances, I will allow people who have already been seen get surprise against someone by leaving their sight before attacking.

For instance: I'm have having a negotiation with 2 diplomats, we are discussing trade agreements between our two countries. One of them gets up and says he is going to get more tea. I believe him. Then the other one starts telling me what terms they would like in the trade deal and I'm so distracted, I forget to look behind me. I feel the dagger buried in my back without even realizing that the other one snuck up on me.

But I adjudicate this situation the same way I do all other Surprise situations. The person sneaking up needs to make a Stealth check vs PP and they need to be unseen to start hiding. But, as per the rules, the DM can determine that a creature is so distracted by something that you can sneak up on them even without cover to hide behind.

However, it should be noted that even in this situation, Surprise is still determined the same way: Stealth vs PP and if the target is unaware of any threat then they are surprised.

If the situation was instead that the two diplomats, in the middle of negotiations started casting spells or pulled out weapons and attack, that isn't surprise. I see you pull out weapons or start casting a spell and I have the ability to react before you finish.
 

I'm not thrilled with some of the, "Make scouting quick and easy" ideas being discussed. That's an important part of the game for most parties (aka exploration).

I agree, but I think the handling time is relative. There's probably room for a lot of groups to shave off some time here and there with succinct descriptions, fast declaration of actions, quick resolution, and keeping things moving forward as compared to whatever they're doing now. It still won't be super-fast or leave off any of the fun bits of exploration challenges, but might be much improved in getting to the action.
 

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