Character Concept: Halfling Rogue/Warlock. Help to refine concept.

[Sir Stig]

I have started playing a Halfling Rogue (premade sample character), criminal background. I have not decided which direction I will follow, but I want to incorporate Warlock into the build, but I don't want to be a standard only EB spellcaster. Since I have not played D&D for 20 years it is likely to be holes in my builds, which I hope you will help me by pointing out, as well as suggestions for improvement. Either way, I want the concept to make sense, and the roleplay aspect are slightly more important than min/max, but I still want to make the optimal character without breaking character. So to speak.

First, a rule question, because it will affect many choices: With Crossbow Expert and a hand crossbow, I get a second attack as a bonus action on the same turn. Will sneak attack damage also apply to this bonus attack?

I will update as I get feedback: Updated Once.

Concept 1: Hit n' Run. Rely on improved criticals, stab with rapier and hand crossbow for sneak attack, then switch to pact weapon and be support sniper:
Scout 13/Hexblade 7
Current abilities: STR 8, DEX 16, CON 12, INT 13, WIS 10, CHA 16

Pact of the blade
Feats: Crossbow Expert (and Sharpshooter?)
Invocations: Burning Hex. Improved Pact Weapon (light crossbow)
Spells: Greenflame blade,

Weapons: Rapier, Hand Crossbow, light crossbow.

Concept 2: Tentacle Assassin that can also play mind games. Based on a sample character for an starting adventure (Phandalin/Glasstaff/Redbrands). I disagreed with some of Glasstaffs methods and I nearly got killed by someone in the Redbrands (which I worked for as a recruiter). Now I want revenge on that person or persons, and Glasstaff.

He didn't almost get killed. He actually died and while in Limbo/Bardo something from another world tainted him. The only thing he knows is that when he came to his senses he was naked in a mortuary/cemetary. His belongings was delivered to his aunt, which was in shock. "They told me you were dead" etc. He is unaware of his warlock bond (still only level 1 rogue). I plan to play out a gradual transition to when I add warlock levels. Like puking slugs and strange/hideous nightmares and visions. True neutral, following his own inner moral compass, no interest in causing suffering or making things worse than they are. I got to swap my playing cards for Tarot cards (which playing cards are based on), and plan to use a tarot deck to spice up the game and improvise (my group does not know I know nothing about Tarot, so I am going to bluff a lot). That's what I've got so far.

It seems like I will go Dex for attacks and defense,

In a party with a Cleric, a Sorcerer and two fighters (one close quarter and one ranged). Still level 1, so I don't know which way they will develop.

Swashbuckler 11/Warlock - GOO, Hexblade or The Undying 6/Battle master 3 (for Riposte (and the bonus damage from superiority dies) and Defense since it specifies +1 bonus and I assume not limit on 20Dex)
Current Abilities: STR 8, DEX 16, CON 12, INT 13, WIS 10, CHA 16
Goal Abilities: STR 8, DEX 20, CON 12, INT 13, WIS 10, CHA 18

Pact of the blade
Cantrips
- (considering EB for this build, If my DM will let me color it as tentacles shooting out).
- (Greenflame blade)
-

Invocations:
- (Claw of Acamar Edit: just noticed it is not a finesse weapon. Do the rogue class give me attack roll with dex?) Can't use this with this build.
- Eldricht Smite (If it stack with Claw of Acamar - do I get this bonus in addition to the bonus CoA when I burn Spell slots?)[S]
- Agonising Blast
- Devils sight

Spells:
- Armor of Agathys

- Mind Spike

[S]- Evald's Black Tentacles

Weapons: Rapier

Got a little messy with all the parantheses. Lots of questions. I think concept 2 is the better visual concept, and as I wrote this I get more sold on that idea. Not sure if it will work, so improvements that fits the concept are most welcome. I would also like suggestions for leveling order.

[Unoriginal]

Sneak attack only applies once per turn. Only way to have two Sneak Attacks in the same round is if you can get an attack with your turn and one out of it (via Commander Strike, for example).

As for your concepts, I'm kinda confused. Can you tell us more abour who those characters are?

If you want mind games, Mastermind or Inquisitive Rogue could work. And a rapier can be a Pact weapon, unless I'm mistaken.

[CTurbo]

I HIGHLY recommend Swashbuckler Rogue to go along with your Warlock. Hexblade with Blade pact could be cool. Chain pact would too with an invisible Imp. Fiend gets you temp hit points per kill.

Either way I'd spam Booming Blade and Green Flame Blade for sure. Shadow Blade would be a great use of your concentration as would Darkness with the Devil's Sight invocation.

I would take more Rogue levels than Warlock though as I feel like you'd get more from the Rogue class.

A few levels of BM Fighter late for Riposte would be good, or you can take the Sentinel feat.

This is actually going to be one of my next characters. A Swashbuckler Warlock that spams Booming Blade, Shadow Blade, and has a reliable reaction attack to utilize sneak attack damage again each round. I just need to be a little tougher than normal in order to hang around in melee better. I may even take Sentinel AND 3-5 levels of BM Fighter for Riposte. Maybe even War Caster too to use Booming Blade with my reaction attacks.

[Keravath]

Which character concept do you prefer? Ranged, melee or a combination of both?

Sneak attack applies once per turn. It applies when you have an ally attacking your target or any time you have advantage on the attack. Looking at ways to generate advantage can guide your choices a bit. Some of the ways to get advantage are:
- help action from a familiar
- bonus action hide (assuming suitable cover) followed by an attack while hidden.
- someone casts faerie fire
- greater invisibility
- darkness + devil's sight ... if your target can't see you but you can see them you get advantage on the to hit roll AND sneak attack damage.

Every two levels of warlock reduces your sneak attack dice by one.

Do you want to take mostly rogue levels early/warlock levels or a mix? How the character builds and levels is more important than where it ends up at level 20.

For a melee focused rogue/warlock ... swashbuckler+hexblade works well. Hexblade lets you use medium armor, martial weapons proficiency, use charisma for attacks with your designated weapon or pact weapon, booming blade or green flame blade. If you choose improved pact weapon you can use charisma as the stat to hit with a ranged weapon (and it is +1 to hit). (Keep in mind that this character won't work for Adventurer's League play because it take spells from SCAG and character options from Xanathar's and breaks the +1 source rule).

Some of the sneak attack damage lost to warlock levels might be compensated for by using the hex spell.

By using hexblade you can also focus on cha and leave dex at 14 wearing medium armor.

If you choose another warlock archetype, you will probably want to focus on dex and use rogue weapons.

Longer term you will want to consider how much warlock you want in the build. Level 5 can get you thirsting blade (which gives you extra attack which is very useful for a rogue since it gives you two opportunities to land a sneak attack).

As a halfling, you may want to consider the Devil's Sight invocation. A halfling doesn't have dark vision .. so without devil's sight or a magic item like Goggles of the Night, you won't be able to operate in dark or dimly lit conditions.

Another point to consider is that a single level of Fighter will give the archery +2 to hit with ranged weapons fighting style that would help with a ranged build.

Two weapon fighting is also a viable option for a melee rogue since the bonus action attack will give you a second opportunity to land a sneak attack. This works particularly for a swashbuckler who has the ability to move away from someone they have attacked without receiving an opportunity attack.

Arcane trickster can also work with warlock since it gives you additional spell casting options and spell slots as well as another route to get a familiar if you decide to go blade pact on the warlock side.

If you are interested in the cross bow expert/sharpshooter type of build then this works better with getting extra attack as quickly as possible. Battlemaster fighter or ranger is probably the better choice for that than warlock due to the archery fighting style and combat maneuvers.

Sharpshooter doesn't really synergize that well with rogue since they only get the one attack typically ... most of the damage comes from the sneak attack dice in many cases. It can certainly be done but you would probably want to aim for extra attack ASAP.

Cross bow expert has the down side that the extra attack uses your bonus action which conflicts with the use of hex and cunning action. However, it does allow for a second ranged attack with a hand crossbow ... unfortunately, improved pact weapon doesn't allow the use of hand crossbows for some reason.

So ... whichever build you go with there are some trade offs. On the other hand, I have a 3 rogue arcane trickster/3 fey warlock blade pact who focuses on dex and ranged attacks that is fun to play but it isn't an optimized build since some of the decisions are made for role play reasons (ie fey vs hexblade).

[MagneticKitty]

A weapon has to specifically say finesse to count.

I would dip Warlock and go mostly rogue swashbuckler.
Attacks of opportunity can be sneak attack. Swashbuckler gives you sneak if you're 1 v 1 a single enemy. Basically one attack per turn means you can sneak attack if you can do an attack on someone else's turn. Such is a reaction or if you're commanded to by the cleric class that does that. Or if you have retaliate from barb.

You can sneak attack with strength if the weapon is finesse.

I would do Warlock blade pact / fiend or hexblaxe would be the optimizer way of doing it. Hexblade is a little less needed since you can't do a SAD cha build when rogue requires dex for stuff.

If you're inclines to do more than 3 of warlock, I'm partial to raven queen patron (turn into a bird at lv 6 which fly and scouting as a raven is great for someone as sneaky as a rogue). At level 10 you get more defenses good for a melee character. Also you can play a race with no darkvision since the raven can give it to you.

[Sir Stig]

1 Sneak attack only applies once per turn. Only way to have two Sneak Attacks in the same round is if you can get an attack with your turn and one out of it (via Commander Strike, for example).

2 As for your concepts, I'm kinda confused. Can you tell us more abour who those characters are?

3 If you want mind games, Mastermind or Inquisitive Rogue could work. And a rapier can be a Pact weapon, unless I'm mistaken.
1: Ahah, that clarifies it. So I need to find the best way to get reaction attacks.
2: Both are based on a sample character for an starting adventure (Phandalin/Glasstaff/Redbrands). I disagreed with some of Glasstaffs methods and I nearly got killed by someone in the Redbrands (which I worked for as a recruiter). Now I want revenge on that person or persons, and Glasstaff.

Concept 1 is just a tactical idea, not given much thought to the personality. The above applies and maybe I can adapt the story below, should I choose to go this route.

Concept 2 I imagine that he didn't almost get killed. He actually died and while in Limbo/Bardo something from another world tainted him. The only thing he knows is that when he came to his senses he was naked in a mortuary/cemetary. His belongings was delivered to his aunt, which was in shock. "They told me you were dead" etc. He is unaware of his warlock bond (still only level 1 rogue). I plan to play out a gradual transition to when I add warlock levels. Like puking slugs and strange/hideous nightmares and visions. True neutral, following his own inner moral compass, no interest in causing suffering or making things worse than they are. I got to swap my playing cards for Tarot cards (which playing cards are based on), and plan to use a tarot deck to spice up the game and improvise (my group does not know I know nothing about Tarot, so I am going to bluff a lot). That's what I've got so far.

3: Yes, rapier can be a pact weapon, but I wanted to have the Claw of Acamar (GOO+blade pact). But if I can't use my Dex or Cha to attack with it, I am better of with just the standard rapier. Maybe I will consider a whip, even with 4 reduced potential damage :/.

I HIGHLY recommend Swashbuckler Rogue to go along with your Warlock. Hexblade with Blade pact could be cool. Chain pact would too with an invisible Imp. Fiend gets you temp hit points per kill.

Either way I'd spam Booming Blade and Green Flame Blade for sure. Shadow Blade would be a great use of your concentration as would Darkness with the Devil's Sight invocation.

I would take more Rogue levels than Warlock though as I feel like you'd get more from the Rogue class.

A few levels of BM Fighter late for Riposte would be good, or you can take the Sentinel feat.

This is actually going to be one of my next characters. A Swashbuckler Warlock that spams Booming Blade, Shadow Blade, and has a reliable reaction attack to utilize sneak attack damage again each round. I just need to be a little tougher than normal in order to hang around in melee better. I may even take Sentinel AND 3-5 levels of BM Fighter for Riposte. Maybe even War Caster too to use Booming Blade with my reaction attacks.
Booming blade is so noisy, sure to alert every enemy around, but Riposte is nice as is the ekstra buff from fighter. I might dip into it, but I would prefer if I can hide or roll out of the way.


Which character concept do you prefer? Ranged, melee or a combination of both?

Sneak attack applies once per turn. It applies when you have an ally attacking your target or any time you have advantage on the attack. Looking at ways to generate advantage can guide your choices a bit. Some of the ways to get advantage are:
- help action from a familiar
- bonus action hide (assuming suitable cover) followed by an attack while hidden.
- someone casts faerie fire
- greater invisibility
- darkness + devil's sight ... if your target can't see you but you can see them you get advantage on the to hit roll AND sneak attack damage.

Every two levels of warlock reduces your sneak attack dice by one.

Some of the sneak attack damage lost to warlock levels might be compensated for by using the hex spell.

As a halfling, you may want to consider the Devil's Sight invocation. A halfling doesn't have dark vision .. so without devil's sight or a magic item like Goggles of the Night, you won't be able to operate in dark or dimly lit conditions.
Whoa, that was a thorough reply. I split and rearranged your quote a bit to answer different points. I think Melee is the way I want to pursue, focusing on getting advantage and reflex opportunities, hiding behind teammates and popping in and out of action. I am looking to boost my sneak attack through the warlock invocations, cantrips and spells, and maybe add some poison to top it off. Even if I lose a few sneak attack d6's, I can get 2-3 d8's from different warlock stuff, in addition to Cha bonus on top. And a little more personality flair. I suspect I am at the point where I mostly see opportunities, and not the limitations though...


Do you want to take mostly rogue levels early/warlock levels or a mix? How the character builds and levels is more important than where it ends up at level 20.

For a melee focused rogue/warlock ... swashbuckler+hexblade works well. Hexblade lets you use medium armor, martial weapons proficiency, use charisma for attacks with your designated weapon or pact weapon, booming blade or green flame blade. If you choose improved pact weapon you can use charisma as the stat to hit with a ranged weapon (and it is +1 to hit). (Keep in mind that this character won't work for Adventurer's League play because it take spells from SCAG and character options from Xanathar's and breaks the +1 source rule).

By using hexblade you can also focus on cha and leave dex at 14 wearing medium armor.

If you choose another warlock archetype, you will probably want to focus on dex and use rogue weapons.

Longer term you will want to consider how much warlock you want in the build. Level 5 can get you thirsting blade (which gives you extra attack which is very useful for a rogue since it gives you two opportunities to land a sneak attack).

How the character levels:
-Maybe go Rogue1/warlock3 to get access to invocations, pact, and get to play around with cantrips and spells (Arms of Hadar for everytime I get caught, Mind spike for damage and location of target).
-Then maybe 1 level fighter(defense, dueling or two weapon fighting)
-before I take rogue up to 5
-2 more lvls fighter.
-Warlock to 5 for extra attack
- then continue as Rogue to 9.
-Warlock to 7
-Rogue x

This gets harder and harder the more I think about it, hehe.

I don't know what the adventurers league is. I play with 5 friends, and think we will stick to that for quite a while.



Two weapon fighting is also a viable option for a melee rogue since the bonus action attack will give you a second opportunity to land a sneak attack. This works particularly for a swashbuckler who has the ability to move away from someone they have attacked without receiving an opportunity attack.

Arcane trickster can also work with warlock since it gives you additional spell casting options and spell slots as well as another route to get a familiar if you decide to go blade pact on the warlock side.
Do you think these fit for my character concept/personality/background? (see above)



Another point to consider is that a single level of Fighter will give the archery +2 to hit with ranged weapons fighting style that would help with a ranged build.

If you are interested in the cross bow expert/sharpshooter type of build then this works better with getting extra attack as quickly as possible. Battlemaster fighter or ranger is probably the better choice for that than warlock due to the archery fighting style and combat maneuvers.

Sharpshooter doesn't really synergize that well with rogue since they only get the one attack typically ... most of the damage comes from the sneak attack dice in many cases. It can certainly be done but you would probably want to aim for extra attack ASAP.

Cross bow expert has the down side that the extra attack uses your bonus action which conflicts with the use of hex and cunning action. However, it does allow for a second ranged attack with a hand crossbow ... unfortunately, improved pact weapon doesn't allow the use of hand crossbows for some reason.
I think I will abandon the ranged weapon idea. Or even mid-range, since there is no way I can use the Claw of Acamar with my low strength. Must be if my DM let me swap STR and I get to dump INT. But then I still don't get to use Dex or Cha for attack. Bye bye, Claw of Acamar, you sounded awesome, but could not fit into any of my development plans.

[CTurbo]

Booming Blade is too good to pass up on a Swashbuckler. At level 5, You walk up and attack an enemy(with advantage) with a Rapier for 2d8+Dex+3d6 damage and then simply walk away from it. If that enemy follows you on it's turn, it takes an extra 2d8 damage. Add an extra 2d8 to the attack if you were concentrating on Shadow Blade. At level 11, your one attack with Booming Blade would be doing 3d8+Dex+6d6 and the enemy would take an extra 3d8 if they move. By this point, Shadow Blade would add an extra 3d8 to the attack. You can repeat this damage every turn with any opportunity attack you can make from Riposte or Sentinel.

Be careful with character levels though, if you go Rogue 3/Warlock 3/Fighter 3, it'd be level 10 before you even got your first ASI/feat.