Timberherethere
2019-02-11, 04:57 PM
or "Why Assassin Rogues are usually bad whenever there is at least one allied creature that does not fare too well on stealth checks"
EDIT: This guide does not work for 95% of tables, read at own risk. Your enemies will not be surprised if they detect a threat, they will not be surprised if they do not detect a threat but do detect a threat at the same time.
Below are four steps for a good assassination attempt: (Which were elaborated under the assumption that one hidden creature was able to surprise all of their enemies in combat even when allies of the hidden creature weren't hiding, a ruling that depends on the DM. If you want to be able to pull off an assassination, you will need to be the party's scout, 120 feet of natural Darkvision from the Observant Skulker Deep Gnome mentioned in "Having a friend goes a long way" plus somehow access to the Message cantrip, or Magic Initiate feat choosing Wizard for Find Familiar to make a tiny Spider walk under doors for you, Minor Illusion to hide like mentioned in "Races" and Mage Hand for utility; Expertise in Stealth, Perception, Investigation and Survival. Being a scout is very costly, being an Assassin then becomes double costly and requires the party to let you scout for them, which is not always guaranteed to happen...)
Step one - Concealment: You need to be hidden in order to surprise your enemies when combat begins, so, before rolling your initiative, tactfully inquire the DM if any of your foes is surprised, if any of them can see you or know where you are before you roll your initiative (each enemy's passive wisdom (perception) needs to be higher than your stealth check in order for each of them, individually, to not be surprised when the combat begins). Try being on the far back rank of the party according to the marching order and do your best to stay hidden from whatever might come at whoever is in the front rank. Avoid being near the front rank if you don't have a way to conceal yourself (assassins, unlike arcane tricksters, can't learn the invisibility spell without multiclassing, using a magic item, or some other mean). You can be in the middle rank behind the front if you are adjacent to a wall and are going to turn a corner or something, just make sure you are doing your best to hide from enemies. Allies, by the way, might comment on how you are acting silly and/or cowardly, and you've got to put up with that somehow, because if you talk back, you raise the odds of enemies discovering your current location.
Step two - Timing: Be patient. Rushing an assassination is bad behavior. You are guaranteed to jeopardize not only yourself, but your entire group at some point if you frequently attempt assassinations out of combat and against your team's wishes. Wait for the DM to ask everyone for their initiative, then you might get to do your thing when combat begins.
Step three - Initiative: You must act before your assassination target, so you need to have a good initiative.
Step four - Accuracy: Your attempt will only yield any result at all when you manage to hit your target. Make sure your accuracy is at its peak whenever you attempt an assassination, because you almost never know for sure if your target is a common enemy or a special one with improved armor, health, legendary resistances and whatnot.
That's it. Make sure you are hidden from possible threats and wait for the DM to ask for initiative, then you tactfully and politely ask for surprise before you roll your initiative. Do not engage combat on your own accord. You are in a party, it must be the party's decision to engage combat whenever the party gets to make that decision together.
Races
The Forest Gnome has Darkvision and knows Minor Illusion at level one, which makes them ideal assassins since they have a way to see in darkness and also cast illusions to conceal themselves. Illusions, by the way, only impair the senses of creatures that might truly believe in them, so, since you know you are casting an illusion, you do not truly believe in your own illusion, therefore, you can automatically see through them, as can anyone who notices you casting an illusion, UNLESS the spell description specifically contradicts this, but, usually, lower level illusions tend to end their description with: "If a creature discerns the illusion for what it is, the illusion becomes faint to the creature.". Forest Gnome Assassin Rogues might want to invest in their Intelligence score to raise the credibility of their Minor Illusion.
The High Elf also has Darkvision and the ability to get Minor Illusion right from the start, plus they get additional weapon proficiencies and are medium sized characters, which synergizes well with the out of combat assassin class features. Their "sleep" takes less time as well, they are faster in combat, have innate proficiency in the perception skill (very common skill check) plus other race specifics you might want to look into.
Feats and multiclassing (in order of importance considering the four steps for a good assassination attempt):
Alert: +5 initiative and immunity to surprise from enemy ambushes.
Crossbow Expert: Allows two assassination attempts from 30 feet when you wield a hand crossbow on one hand and your other hand is free to reload it with ammunition.
You might want to delay your ability score increase of 10th Level in favor of multiclassing Fighter so that you pick the Archery fighting style, learn Action Surge and become a Battle Master who knows the Precision Attack maneuver (other picks for maneuvers could be Riposte and Maneuvering Attack, Riposte can be combined in melee with the Sentinel feat to get a sneak attack out of your reaction, because you can sneak attack on different turns in the same round). Multiclassing in Fighter means that you will delay your 17th level Death Strike and also the progression of your sneak attack damage. Certain creatures can choose to automatically succeed on failed saving throws a limited amount of times, therefore it is up to you if you want them to spend one of these as soon as 17th level or later should they even fail it, which they likely won't anyway, so think about that.
Sharpshooter/Ritual Caster/Lucky: Good choices, remember to keep your accuracy high on your assassination attempt.
Dexterity: Invest in your Dexterity score as soon as you decide that it is worthwhile considering that it generally improves your stealth, your initiative, your chance to hit, your damage, your armor class, your acrobatics, your sleight of hand, your dexterity saving throw/checks and most of your thieves' tools checks as well.
Having a friend goes a long way
Assassins seem to spend a lot of resources in order to further develop their trade, so they could end up not being as adept at perceiving things around them as they possibly could. A really good match to watch an Assassin's back would be a Deep Gnome (from the Sword Coast Adventurer's Guide or Mordenakinen's Tome of Foes) since they begin with Superior Darkvision (and no Sunlight Sensitivity), therefore the Observant and Skulker feats would together provide +10 Passive Perception for them in natural darkness up to 120 feet (two levels in the Warlock class would give them access to the Devil's Sight invocation, which can replace the Skulker feat. They still benefit quite a bit from having their racial 120 feet of Darkvision though since the invocation does not affect natural dim light at all, only natural and magical darkness). Three levels in the Trickery Domain of the Cleric class would make it possible for them to provide advantage on stealth checks for one character other than themselves (Blessing of the Trickster) while concentrating on Pass Without Trace (+10 stealth) for the entire party.
It's possible to sneak attack on an ally's turn when they effectively use the Commander's Strike maneuver acquired from either the Martial Adept feat or the Battlemaster Fighter class.
Scouting ahead
Arcane Trickster Rogues learn spells and don't need to stress over their initiative like Assassins do, so it's usually better for the party to have an Arcane Trickster scout dangers ahead and then come back with information so that the party can formulate a plan together. There needs to be only one scout in the party if any at all, really, it can be a Monk, a Pact of the Chain Warlock familiar, a tanky character with good scores and skills for scouting, anyone with the ability to perform the task, but Assassins, if they're dedicated to their features and abilities, are usually ill suited to fill the scout role of a party, because they might be seen in the open and then they can't assassinate their enemies since they won't be surprised.
Additional notes
The Gloom Stalker Ranger (from Xanathar's Guide to Everything) receives a bonus to their initiative roll that equals their Wisdom modifier.
Thank you for reading, have a great day and a great game. youtube.com/watch?v=sxjbZ3k1UiI
Edit: Thank you monkey3 for pointing out the High Elf.
EDIT: This guide does not work for 95% of tables, read at own risk. Your enemies will not be surprised if they detect a threat, they will not be surprised if they do not detect a threat but do detect a threat at the same time.
Below are four steps for a good assassination attempt: (Which were elaborated under the assumption that one hidden creature was able to surprise all of their enemies in combat even when allies of the hidden creature weren't hiding, a ruling that depends on the DM. If you want to be able to pull off an assassination, you will need to be the party's scout, 120 feet of natural Darkvision from the Observant Skulker Deep Gnome mentioned in "Having a friend goes a long way" plus somehow access to the Message cantrip, or Magic Initiate feat choosing Wizard for Find Familiar to make a tiny Spider walk under doors for you, Minor Illusion to hide like mentioned in "Races" and Mage Hand for utility; Expertise in Stealth, Perception, Investigation and Survival. Being a scout is very costly, being an Assassin then becomes double costly and requires the party to let you scout for them, which is not always guaranteed to happen...)
Step one - Concealment: You need to be hidden in order to surprise your enemies when combat begins, so, before rolling your initiative, tactfully inquire the DM if any of your foes is surprised, if any of them can see you or know where you are before you roll your initiative (each enemy's passive wisdom (perception) needs to be higher than your stealth check in order for each of them, individually, to not be surprised when the combat begins). Try being on the far back rank of the party according to the marching order and do your best to stay hidden from whatever might come at whoever is in the front rank. Avoid being near the front rank if you don't have a way to conceal yourself (assassins, unlike arcane tricksters, can't learn the invisibility spell without multiclassing, using a magic item, or some other mean). You can be in the middle rank behind the front if you are adjacent to a wall and are going to turn a corner or something, just make sure you are doing your best to hide from enemies. Allies, by the way, might comment on how you are acting silly and/or cowardly, and you've got to put up with that somehow, because if you talk back, you raise the odds of enemies discovering your current location.
Step two - Timing: Be patient. Rushing an assassination is bad behavior. You are guaranteed to jeopardize not only yourself, but your entire group at some point if you frequently attempt assassinations out of combat and against your team's wishes. Wait for the DM to ask everyone for their initiative, then you might get to do your thing when combat begins.
Step three - Initiative: You must act before your assassination target, so you need to have a good initiative.
Step four - Accuracy: Your attempt will only yield any result at all when you manage to hit your target. Make sure your accuracy is at its peak whenever you attempt an assassination, because you almost never know for sure if your target is a common enemy or a special one with improved armor, health, legendary resistances and whatnot.
That's it. Make sure you are hidden from possible threats and wait for the DM to ask for initiative, then you tactfully and politely ask for surprise before you roll your initiative. Do not engage combat on your own accord. You are in a party, it must be the party's decision to engage combat whenever the party gets to make that decision together.
Races
The Forest Gnome has Darkvision and knows Minor Illusion at level one, which makes them ideal assassins since they have a way to see in darkness and also cast illusions to conceal themselves. Illusions, by the way, only impair the senses of creatures that might truly believe in them, so, since you know you are casting an illusion, you do not truly believe in your own illusion, therefore, you can automatically see through them, as can anyone who notices you casting an illusion, UNLESS the spell description specifically contradicts this, but, usually, lower level illusions tend to end their description with: "If a creature discerns the illusion for what it is, the illusion becomes faint to the creature.". Forest Gnome Assassin Rogues might want to invest in their Intelligence score to raise the credibility of their Minor Illusion.
The High Elf also has Darkvision and the ability to get Minor Illusion right from the start, plus they get additional weapon proficiencies and are medium sized characters, which synergizes well with the out of combat assassin class features. Their "sleep" takes less time as well, they are faster in combat, have innate proficiency in the perception skill (very common skill check) plus other race specifics you might want to look into.
Feats and multiclassing (in order of importance considering the four steps for a good assassination attempt):
Alert: +5 initiative and immunity to surprise from enemy ambushes.
Crossbow Expert: Allows two assassination attempts from 30 feet when you wield a hand crossbow on one hand and your other hand is free to reload it with ammunition.
You might want to delay your ability score increase of 10th Level in favor of multiclassing Fighter so that you pick the Archery fighting style, learn Action Surge and become a Battle Master who knows the Precision Attack maneuver (other picks for maneuvers could be Riposte and Maneuvering Attack, Riposte can be combined in melee with the Sentinel feat to get a sneak attack out of your reaction, because you can sneak attack on different turns in the same round). Multiclassing in Fighter means that you will delay your 17th level Death Strike and also the progression of your sneak attack damage. Certain creatures can choose to automatically succeed on failed saving throws a limited amount of times, therefore it is up to you if you want them to spend one of these as soon as 17th level or later should they even fail it, which they likely won't anyway, so think about that.
Sharpshooter/Ritual Caster/Lucky: Good choices, remember to keep your accuracy high on your assassination attempt.
Dexterity: Invest in your Dexterity score as soon as you decide that it is worthwhile considering that it generally improves your stealth, your initiative, your chance to hit, your damage, your armor class, your acrobatics, your sleight of hand, your dexterity saving throw/checks and most of your thieves' tools checks as well.
Having a friend goes a long way
Assassins seem to spend a lot of resources in order to further develop their trade, so they could end up not being as adept at perceiving things around them as they possibly could. A really good match to watch an Assassin's back would be a Deep Gnome (from the Sword Coast Adventurer's Guide or Mordenakinen's Tome of Foes) since they begin with Superior Darkvision (and no Sunlight Sensitivity), therefore the Observant and Skulker feats would together provide +10 Passive Perception for them in natural darkness up to 120 feet (two levels in the Warlock class would give them access to the Devil's Sight invocation, which can replace the Skulker feat. They still benefit quite a bit from having their racial 120 feet of Darkvision though since the invocation does not affect natural dim light at all, only natural and magical darkness). Three levels in the Trickery Domain of the Cleric class would make it possible for them to provide advantage on stealth checks for one character other than themselves (Blessing of the Trickster) while concentrating on Pass Without Trace (+10 stealth) for the entire party.
It's possible to sneak attack on an ally's turn when they effectively use the Commander's Strike maneuver acquired from either the Martial Adept feat or the Battlemaster Fighter class.
Scouting ahead
Arcane Trickster Rogues learn spells and don't need to stress over their initiative like Assassins do, so it's usually better for the party to have an Arcane Trickster scout dangers ahead and then come back with information so that the party can formulate a plan together. There needs to be only one scout in the party if any at all, really, it can be a Monk, a Pact of the Chain Warlock familiar, a tanky character with good scores and skills for scouting, anyone with the ability to perform the task, but Assassins, if they're dedicated to their features and abilities, are usually ill suited to fill the scout role of a party, because they might be seen in the open and then they can't assassinate their enemies since they won't be surprised.
Additional notes
The Gloom Stalker Ranger (from Xanathar's Guide to Everything) receives a bonus to their initiative roll that equals their Wisdom modifier.
Thank you for reading, have a great day and a great game. youtube.com/watch?v=sxjbZ3k1UiI
Edit: Thank you monkey3 for pointing out the High Elf.