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Sharpshooter is considered to be among the most overpowered feats in D&D 5e. Its gross damage boost is even more pronounced when one has a consistent source for Advantage.

Gloom Stalker has the following feature at level 3:

UMBRAL SIGHT (...) While in darkness, you are invisible to any creature that relies on darkvision to see you in that darkness.

Fine in a city or wilderness adventure, where it's only dark occasionally, but in dungeon adventures, darkness is prevalent. And when the campaign is a megadungeon campaign, that is dungeon all the time. Even if there is light somewhere, it is sufficient that the Gloom Stalker shoots out of an area of darkness to gain the benefit of invisibility. It is nearly like having permanent Greater Invisibility going.

Being invisible grants Advantage. So nearly all of the time, these Sharpshooter attacks are made with Advantage. Together with Archery, this effectively negates the -5 penalty to attack rolls from Sharpshooter.

Gloom Stalker at 3rd level also gets Dread Ambusher, which adds his wisdom bonus to Initiative, and gives an additional attack with +d8 damage if he attacks in the first round. As a Ranger, at 5th level he gets yet another Extra Attack.

Our situation

We are playing Dungeon of the Mad Mage, so we are in dark dungeons a lot of the time. Our party has three characters of 12 level (currently), all with darkvision, a plain vanilla Wizard 12, a Paladin 6/Sorcerer 6, and the Gloom Stalker, a Ranger 6/Rogue 5/Cleric 1.

He took a level of War Domain Cleric, for yet another set of Extra Attacks and Bless to further boost his hit rate, and a few levels of Rogue for Sneak Attack damage. We often Haste him, as he has the highest damage output per attack, even higher than our Paladin.

I think we all have competent character builds, but in the face of a typical combat opening to a flurry of 5 attacks with Advantage, each dealing 20 damage or so on average, few opponents live to see the end of their second round. Nevermind if he rolls a critical, which, given the many attacks, is not that rare. I like it, it makes our life easy. But I pity our poor GM who has to put up with this.

Issues this has been causing

  • The brutal effectiveness of the Gloom Stalker invalidates many fun, but less effective tactics. It is just not worth the effort to try something else when he just can mow down everything.
  • Our GM likes to play by rules as written, but has taken to rulings that often feel biased, in an attempt to keep the game challenging and make things more difficult. (We are only 3 PCs, instead of 4, but deal with all the same challenges).
  • For example, originally in the campaign it was very hard for us to detect and pinpoint invisible enemies. When the Gloom Stalker came into swing, invisibility suddenly was reduced to the pure mechanistic minimal effect (after heavily consulting this site as to what that would be :)).
  • The GM has tried other things like Faerie Fire by the drow, but the accessibility of Haste and high mobility of the rogue with Cunning Action make it easy to evade light areas, and even allow for a Hide action every round invisibly. The long range of the longbow allows the Gloom Stalker to make full use of his mobility and shoot into light areas from the dark. It even may harm the opponents, as he can see into the lighted area from further out than his darkvision's reach.
  • The GM regularly coordinates the intelligent monsters to "monster-ball" us with most of the monsters on a level in one combat to overload our kill rate. We had that against the drow twice, and against the nagas and bulliwugs. We still won one of these, and took a tactical retreat after causing severe losses in the other two. When I tally these fights on Kobold Fight Club, they typically end up with 5-10 times the XP worth of what would constitute a "deadly" encounter for four characters of our level.

Is the Gloom Stalker overpowered?

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9 Answers 9

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Umbral sight isn't THAT strong

It's a solid ability that I suspect (without looking through every adventure) gets a few uses per session, on average.

The build is optimized for this example

It seems that the Gloom Stalker (more like DOOM Stalker) in question has a stacked deck and the DM refuses to shuffle it.

A dungeon dive (no sunlight?) ☑ check
Fighting in dark areas? ☑ check
Fighting enemies that have darkvision? ☑ check
The party has darkvision? ☑ check
Build entirely around taking advantage of Umbral Sight? ☑ check
The DM not taking any steps to intercept the ability? ☑ check

What should be done about it?

  1. Before I list my examples, I want to remind you that you know your group better than we do. This might be a good chance for the group to have a discussion about the class interactions. "Hey I didn't know this was this strong and it's kind of harshing our ride. Can we work something out." or whatever. Communication is the key to any group, and especially any gaming group with a lot of fiddly moving parts (rules). Or maybe everyone likes "Gloom Stalker makes enemies go dead" and you just carry on.

That said.

  • Dim light ruins the ability, just shuts it right down. A lot of the areas in DotMM either should be or could be dim light, rather than darkness. Most [citation needed] creatures with natural darkvision don't love living in darkness 100% of the time. Not every area and enemy should be fighting from pitch black.
  • The ability only works on enemies using darkvision to see the Gloom Stalker, so other forms of vision work. I'm not actually 100% sure this is relevant, because I'm not going to go through every enemy in the adventure to confirm it, but it's worth noting.
  • Not every area is a 60-foot kill tunnel that the Gloom Stalker has a perfect angle to shoot through. There should be enemies fighting on corners and cover, not just lining up to be turned into an improvised quiver. (shooting through allies would impose half cover if not for Sharpshooter)
  • Enemies aren't mindless suicide machines. They don't have to be tactical geniuses, but if an entire dungeon floor sends a "monster ball" at the human(oid) nail gun and doesn't win, someone is going to certainly tell someone else about it. And they're going to suggest that the next floor do SOMETHING differently.
  • Not every encounter is combat. There should be more going on than "you walk in and have 30 enemies to shoot at" - not saying you guys aren't doing "soft" skills, but just a good reminder.

Oh, and don't forget that the Gloom Stalker can only see out to 60-90 feet.

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    \$\begingroup\$ I think this is a good take. It would be like asking "Is Pikachu overpowered because it always 1-hit KOs Gyarados with Thunder?" Well, no, you just picked an opponent that is maximally weak to Pikachu. \$\endgroup\$ Commented Feb 4, 2022 at 18:46
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    \$\begingroup\$ @goodguy5: Good point about enemies reacting intelligently. The GM is doing this, so far already two settlements of drow packed up and fled Undermountain (the dungeon) for Skullport (a nearby thieves' den) before we could return to finish them off. We found some levels nearly entirely vacated and stipped of treasure... \$\endgroup\$ Commented Feb 4, 2022 at 19:05
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    \$\begingroup\$ This is good (especially the part that not every underground creature likes to live in complete darkness), but ignores the parts of the question talking about the rest of how this specific character is optimised. A standard no feat single class gloomstalker probably needs this setup to even be effective, it just happens in this case to be tagged on to other optimised features. \$\endgroup\$
    – SeriousBri
    Commented Feb 4, 2022 at 19:24
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    \$\begingroup\$ Also worth bringing up is, if the ranger is cranking out attacks like it sounds from Groody's account, they'll run themselves out of arrows quickly, and unless the party is leaving the dungeon to restock frequently or using spells/raw materials and tools to fabricate more arrows, the ranger will run out of arrows. Per the PHB, in the subsection outlining the Ammunition property in the Weapons section of Chapter 5: Equipment, "at the end of battle, you can recover half your expended ammunition by taking a minute to search the battlefield." The rest are presumably lost or irreparably damaged. \$\endgroup\$
    – Remilia
    Commented Feb 5, 2022 at 18:53
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Is it the feature or the character?

I am wondering at how attributes were determined. Ra6/Ro5/Cl1 only gets 2 ASIs whereas a straight Ro12 would get 4. That extra 4 points makes a difference, and it will only become more pronounced. If die-rolling was used, that often results in characters with high attributes compared to point-buy or standard array, and so you then logically get higher-powered characters than otherwise.

Are some rules being mis-applied or overlooked?

How many arrows does the GS have? It's a trivial example, but it's a finite resource. Are you sure everything the GS is doing is correctly applying every other resource use? Sometimes the perception of OP is that the PCs can too easily take a long rest. Some days the PCs need to run out of everything to really get things to balance.

What's everyone else doing?

Not sure why the other characters aren't dealing some damage of their own. A Wizard 11+ with Summon Elemental and Planar Binding gets a pet elemental that will stick around for 10 days without concentration‡ and don't get me started on divine smite, see here. After all, the GS isn't always going to get initiative.

‡ Sure there's some (imo lame) argument that this won't work RAW but pick a different set of wizard attacks if you want. Banish. Lightning bolt. Long list.

What are the monsters doing?

Sure, some monsters are too dumb to know better but plenty of monsters including ones in DoTMM are smart enough to observe any overused tactic and not just counteract it, but use it as a tactical advantage. If the party is relying on the GS for an initial heavy strike a smart monster commander will lure the GS out then disable with control effects or limit with terrain. Then suddenly the other PCs are bargaining to ransom the GS or hauling the GS out to find a raise dead.

TL;DR

I don't think you can determine if a single feature is overpowered by examining a single set of characters in a particular environment, there are just too many other variables.

But wait...

Clearly there's something about the situation that is not sitting well, or you wouldn't have asked the question. If the DM sees an imbalance there are many ways to gently nudge things in a different direction. Example solutions:

  • The monsters get tactical
  • The monsters turn on the lights
  • The wizard gets some more spells
  • The paly finds a better weapon

Or any number of other things to balance things out.

Good luck!

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    \$\begingroup\$ We used standard point buy for the chacter generation. We have a bag of holding, and carry about 500 arrows in it to not run out. We for sure overlook something here and there -- would be amazing if we did not. We take long rests in Tiny Hut typically, or decamp to the surface. \$\endgroup\$ Commented Feb 4, 2022 at 22:29
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    \$\begingroup\$ The rest is also contributing, just at a lower DPS output. Wizard needs his cash for spell writing, no costly planar bindings :), Wall of Force or Disintegrate will have to do (Portent... unless they have legendary ones, you know they'll fail the save). \$\endgroup\$ Commented Feb 4, 2022 at 22:40
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"While in darkness, you are invisible to any creature that relies on darkvision to see you in that darkness."

Typically in all our dungeons, some light sources are prevalent because the DM likes to use a mix of humans and monsters for villains, such as underground thief networks, evil warriors, necromancers, etc.

All those people would require torches, be they normal or green, purple, or blackfire flames. Any of these would make the ability null and void.

Likewise, outside in moonlight, people can see, though dim, it doesn't classify as darkness, so again, the advantage is negated.

In actual darkness where the purpose is to blind people who can't see, those people don't have darkvision, so they can't see anyway, and everything is invisible to them, and again, the power provides no advantage.

In daylight, which by all reasonable accounts should be at least half your combat, and in places like cities lamps, candles, torches, and chandeliers abounding, there's no logical reason to assume you are surrounded by a plethora of Dark Vision targets in Total Darkness.

The conclusion is therefore, only in settings where its both pitch black and everything you want to kill has dark vision, does this grant similar bonuses to improved invisibility.

I cannot deny that some Dungeon Masters may construct worlds where "everything is in darkness, and everything has darkvision" would make this Over Powered, but I run mixed parties and we are constantly having to use Light Spells and Lanterns. So in our worlds, this power would be so Niche we would think it weak. Remember, you are already invisible to humans and several other races in Darkness. This only provides additional racial sets for that list, and all of them negated with a cheap torch or cantrip.

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    \$\begingroup\$ A note: You say "outside in moonlight, people can see, though dim, it doesn't classify as darkness". The actual rules for vision and light say "A particularly brilliant full moon might bathe the land in dim light." implying even a day or two on either side of a full moon, the moonlight is not enough to lift the darkness. Which makes a sort of sense; a lot of our beliefs about weird stuff happening on full moons is due to that being the only time of the month it was lit enough at night for assignations, criminality, or simply being abroad, without bringing your own light. \$\endgroup\$ Commented Jan 8, 2023 at 13:23
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Is the Gloom Stalker overpowered?

Gloom Stalker is arguably one of the best subclasses in the game, certainly for rangers, especially when the party works together to complement their abilities.

But, the wizard, sorcerer and paladin have great base classes and excellent subclasses. You didn't mention their subclasses, but wizard is arguably the most powerful base class in the game.

Given that, let's do a little math. Your gloom stalker chose the longbow (wise choice as the usual crossbow expert/ bonus action additional attack doesn't synergize well with Hunter's Mark and costs two feats before you have adequate range). Given the party is in darkness, the enemy has no way to counter that and the target has an AC of 16.

Note: I'm using the DMG monster creation tables for guidance, but they do not reflect published monsters. You can read more about the discrepancy and some guidelines based off of published creatures at blog of holdings, "5e monster manual on a business card".

The ranger has an 18 Dexterity, Extra Attack and Sharpshooter and advantage from not being seen. Assume they use their bonus action to cast Hunter's Mark. Also has +1 longbow and +2 for Archery

To hit: proficiency +4, Dex +4, +2 Archery, +1 longbow, Sharpshooter -5 = +6 Hit chance = (20 - (16 - 6))/20 or 50%. Sharpshooter hurts us here, but generally, on average would still outpace not using it. But, we have advantage. To get this calculation accurately, we need to square the miss chance. 1 - 0.5^2 = 0.75

Now let's look at the first attack's damage. Longbow is 1d8, so 4.5 on average, plus Dex 4 plus 10 for sharpshooter plus 3.5 for Hunter's Mark. Because you can add sneak attack to any attack that hits, we'll calculate that separately. Whether you can use Dread Ambusher on the first attack is questionable, so we'll use it on attack 2.

First and third attack (4.5 + 1 + 4 + 10 + 3.5) 23 * 0.75 = 17.25 + Crit 8 (longbow and hunter's mark) * 0.10 = 18

Second attack (DA) (4.5 + 4.5 + 1 + 4 + 10 + 3.5) * 0.75 = 20.6 + Crit 12.5 (LB HM DA) * 0.10 = 21.9

Sneak Attack. What's the chance we hit at least once? 1 - 0.25^3 = 0.98 (1 - 0.25^2 = 0.94 on subsequent rounds) 3d6 = 10.5 * 0.98 = 10.3 + Crit 1 = 11.3 (~10.8 on subsequent rounds)

First round total = 69.2

Subsequent rounds = 46.8

Average (assuming 4 rounds per combat) = 52.4

If this was a single enemy with 240 hp (about average for CR12, according to the DMG), the ranger alone could defeat the enemy in five rounds, if he survives that long. If the party is defeating the enemies in 3-4 rounds, that's about average.

At this level, the warlock baseline (nova) is 26.81, so about two and a half times the baseline, so pretty good build.

If we consider a 12th level basic rules fighter champion, all ASIs to Strength (no feats) wielding a maul with Great Weapon Fighting, their nova is 74 (using Action Surge) and their average (including AS three times over 24 rounds of combat), 41.63. Whether this says perhaps the fighter champion is underrated or the gloom stalker is overrated is up to the reader. These are just numbers and the defensive buffs from mobility are hard to calculate but fantastic. Being able to do this from range is very potent.

Remember, this is considering you always have advantage, which isn't going to be the case 100% of the time. I also included Hunter's Mark on every attack, which is what you want, but won't be the case if you drop more than one opponent per round or any other reason you need to re-target.

It's very good, but no, it is not overpowered

Are you having fun?

This is the most important question, and it looks like you've had some pretty challenging fights given that you've had to retreat a couple of times.

DM Style

After reading some of the comments, it looks like you have a great DM and excellent party tactics.

The Order of Combat

How combat starts when a party uses Stealth is a little tricky. In 99% of cases, it's when the party encounters one or more enemies, but what happens when only one side is aware? I have often allowed parties to do stuff outside of combat and then choose when to start the first round. Likely, there are DMs that run it where as soon as either one of the party or one of the enemy is aware immediately determine who is surprised and roll initiative. The latter is probably a more accurate reading of the Order of Combat. As the gloom stalker likely will have the highest initiative, it makes haste unlikely in round one and if they wait until round two to commence with hostilities, then the gloom stalker will lose Dread Ambusher and more importantly, you will lose the benefit of surprise. You might still retain being unseen, but negative impact on the enemy of surprise will be over.

DM's secret

Some DMs are adversarial, and that's not a lot of fun. There are tells, especially like the DM speaking in first person, "I won initiative." That's usually a sign for me that this group is not for me.

I really like the mention of your DM having intelligent enemies use better tactics. As DM, they have all the information, so could easily metagame tactics the enemy should not have to try and "even the odds". This DM's a keeper. A good DM is on your side.

Keeping it challenging

On the other hand, the DM should be trying to keep things challenging, which can be very difficult running an optimized party through a commercial adventure, especially if there are a lot of solo enemy encounters. You can't simply increase the numbers, as that would likely make it too difficult. Adding one or two enemies of 2 to 3 lower CR helps, but then again, you run into the issue that CR is very unreliable. Lately, I've been using Trekios' battlesim. I don't put the actual party in there, rather I put in a stock party of the same size and level and add monsters until there are one or two dead players at the end. Even minor tactics or surprise is often enough to turn the tide to the players. It really helps as CR is so unreliable. Commercial adventures have some crazy and imbalanced encounters and a tool like battlesim will move the surprise from your game to your planning.

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  • \$\begingroup\$ Thanks for the answer! He does have a magical bow (not unreasonable at this level) for +1 to hit & dmg, and Fighting Style: Archery, from Ranger 2; as variant human by level 8 had two ASI on top of Sharpshooter, so Dex 20 for +5, making his attack total +5 +4 +2 +1 = +12 before the effects of Sharpshooter (-5) and Advantage (depends on AC, but up to +5 to negate it). So I think the hit chance must be at least +4 to hit higher. Dex adds +1 to damage too. He'd typically use his bonus action round 1 not for hunters mark but an attack from War Cleric. \$\endgroup\$ Commented Jul 12, 2023 at 19:05
  • \$\begingroup\$ The wizard is a divination school wizard -- arguably one of the strongest subclasses from what I've heard (we only played with an Abjuration, Evocation and Divination one so far; Portent is very strong) \$\endgroup\$ Commented Jul 12, 2023 at 19:07
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    \$\begingroup\$ Portent is so fun! \$\endgroup\$
    – Wyrmwood
    Commented Jul 12, 2023 at 19:08
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    \$\begingroup\$ Might be also useful to note that the published monsters of CR 12 have an average of about 146 hp (the guidance in the DMG is a fair bit higher than the content of the MM and other sources on actual monsters), but have a slightly better AC closer to 17. \$\endgroup\$ Commented Jul 13, 2023 at 15:13
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    \$\begingroup\$ @Wyrmwood It was "loose" to "lose" that caused me to edit this. I think "lose" is what you really meant, but if I'm wrong of course feel free to reverse. This is a really good answer that didn't get the credit it deserved (as often happens to late answers), glad it got the bounty. \$\endgroup\$
    – Jack
    Commented Jun 19 at 14:56
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A bit late to the party, but I noticed there is one side to umbral sight which has not been discussed here in your scenario. Umbral sight says:

While in darkness, you are invisible to any creature that relies on darkvision to see you in that darkness.

and it seems no ability you can easily turn off. So that being said any creature in your case would include your own party. So if you are in darkness and the enemies cannot see the gloomstalker, your paladin and mage, who rely heavily on darkvision also cannot see the gloomstalker and he/she is invisible to them. Which will, depending on if your DM/groups like this, add some flavor to aspects of healing or buffing him at least.

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    \$\begingroup\$ It is a good point - how funny would it be if the gloomstalker went down to friendly fire because the mage didn't see that they were in the AoE, and then they couldn't be saved by healing word because the cleric couldn't see them! \$\endgroup\$
    – Kirt
    Commented Dec 10, 2023 at 18:40
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It is all in how the dm runs it, in your case.

It is worth noting that in the lore the drow are well trained to fight in pure darkness using their innate darkness ability and elven hearing. If I were running it I would give them some sort of buff to limit it out a bit and/or have them using darkness more.

As others have said, use more dim light environments, even creatures with dark vision don't like total darkness as darkvision just reduces it to dim for them so they have perception penalties plus it has limited range.

Spellcasters may have faerie fire traps and wards, burning oil etc.

Ultimately in the right context these specific abilities are very strong and I think the intent is for planning to be improved to take advantage of these abilities i.e the party can plan to snuff out all the lights in a room before going in to make use of the ability and this is where the spellcasters may shine.

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    \$\begingroup\$ An example of a dim light dark environment can be found in Sunless Citadel (and others) where the walls and floor have a variety of glowing fungus ... \$\endgroup\$ Commented Feb 6, 2022 at 14:17
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Your problem isn't his advantage, your problem is stacking Extra attacks. Your gloom stalker does not have 5 attacks, which is a core of your issues.

The rules for stacking Extra Attack as they relate to non-fighters and fighters are in the Multiclassing section of the Player's Handbook, pg. 164:

If you gain the Extra Attack class feature from more than one class, the features don't add together. You can't make more than two attacks with this feature unless it says you do (as the fighter's version of Extra Attack does). Similarly, the warlock's eldritch invocation Thirsting Blade doesn't give you additional attacks if you also have Extra Attack.

The only class that can expand the ability of Extra Attack to make more than 2 attacks per Attack action is the Fighter. The Fighter's Extra Attack feature says (PHB, pg. 72):

Beginning at 5th level, you can attack twice, instead of once, whenever you take the Attack action on your turn.

The number of attacks increases to three when you reach 11th level in this class and to four when you reach 20th level in this class.

Actually following RAW in this case would make gloom stalker still strong (in this campaign that seems tailored to his strengths), but not completely broken character.

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    \$\begingroup\$ This is the main issue for me, yes the gloom stalker is strong but if you give any class two or three more attacks per turn than they could have RAW then of course they're going to be over powered. \$\endgroup\$ Commented Apr 14, 2023 at 9:31
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    \$\begingroup\$ I think the Gloom Stalkers additional attack is not an Extra Attack in the RAW sense , I will adjust the text to avoid confusion. The Dread Ambusher feature states "If you take the Attack action on that turn, you can make one additional weapon attack as part of that action.", it does not say you get an extra attack. The War priests is neither, it is a bonus action: "When you use the Attack action, you can make one weapon attack as a bonus action." \$\endgroup\$ Commented Apr 14, 2023 at 12:26
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Well, I will keep it brief and to the point: no Gloom Stalker isn't OP unless you built your character to stack damage on the first round of attacks.

If you build is all about quick kills from the shadows, there is very little any group of enemies can do if they are surrounded with darkness.

Your party compounds this effect by casting Haste on this player, which allows it to make an extra attack, so 4 (2 basic, 1 because Dread Ambusher and 1 from Haste) ranged attacks with advantage, combined with Sharpshooter, Sneak Attack and Dread Ambusher for bonus damage. Which means this character deals about 50 DMG in the first round, right?

This seems like the very definition of a "one-trick-pony".

Any battle that is in confined spaces, lot's of blocking terrain and/or enough light sources, can break this combination. I you make combat about melee (by setting up a trap or just the good old bottleneck), this party will struggle is there is more than one front, because the Paladin is the one who can stand his ground.)

In my humble opinion, this is the result of 'gaming the system': optimizing a build of a character to have a DPR as high as possible. This warps all combat around this one build. So the DM can try to pick enemies that counter this trick: maybe look for enemies that are not as susceptible to Piercing damage, like skeletons or more exotic creatures.

My personal approach as a DM would be is to talk about this issue with the party. Is this the playstyle that they like: rarely any combat encounter that is challenging in darkness? I would get bored quite quickly with this kind of gameplay. This is more the gameplay I would build for in a video game. This game is about story telling, which can be done with such a killy character, yet IMHO it typically get's in the way of creating memorable moments, when your characters are on the backfoot and still manage to save the day by some clever interactions with the foes, their environment or by combining their actions together to come out on top/survive.

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  • \$\begingroup\$ I don't see how optimisation gets in the way of storytelling. On the opposite, it seems logical to me that an adventurer in a party would want to focus on doing their one thing well, and leave other roles to party members more fit for it. Could you clarify what part of optimisation causes issues with storytelling? \$\endgroup\$
    – Matthieu
    Commented Jul 17, 2023 at 9:45
  • \$\begingroup\$ Its actually 5 attacks with haste,a s they get a bonus action attack from War Domain cleric 1st, too. \$\endgroup\$ Commented Jul 17, 2023 at 15:03
  • \$\begingroup\$ By my calc they get to 86 expected damage round 1 without haste, and about 50 each round after. The character is not fully optimized for damage here, the player opted to not go down Assassin with his rogue, which would have had a chance to auto-crit on hits. So they can do some other useful stuff, like find secret doors, and disarm traps (and have very high perception in general). You are right on, we'll struggle in multi-front fights, as we are just 3, and I am a squishy wiz (not that squishy thanks to Shield Guardian) \$\endgroup\$ Commented Jul 17, 2023 at 15:33
  • \$\begingroup\$ @Matthieu I can't speak for the author but if you asked me, I'd question for example how they became a cleric, have they always been religious or have they suddenly "found their faith" when it became rather convenient for them in terms of game mechanics. Especially as clerics tend to be deeply religious people in much the same way most rogues tend not to. \$\endgroup\$
    – biziclop
    Commented Jul 17, 2023 at 21:42
  • \$\begingroup\$ In general I feel that in (correctly) trying to fix the rigidity and unfair disadvantage imposed on multiclassing of the early editions, 5e has gone too far the other way, basically you just announce that you want to multiclass to something and if you've got the pre-requisite ability, off you go. But that is altogether a matter of personal preference and it's easy to fix in stories you run. \$\endgroup\$
    – biziclop
    Commented Jul 17, 2023 at 22:09
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It's powerful but too circumstantial.

There is only one - and precisely one - circumstance where Umbral Sight excels which is when you're in total darkness and the enemy has darkvision. It does not help in:

  • dim light where darkvision allows creatures to see without disadvantage
  • blending into foliage with camouflage in dim or bright light
  • Obscured by only mist, smoke or heavy precipitation
  • Peeking out from around total cover without darkness.

Plus, you can already hide from a creature in dim-light as long as there's any other circumstances that contribute to concealment which could be camouflage, range, distraction, etc. If you are in total darkness and a creature is within range of darkvision then you are considered to be in dim-light which is lightly obscured.

The only way it helps is to make you categorically invisible but you still have to make a Dexterity (stealth) check to avoid being noticed just from noise and footprints, etc.

There's not much mechanical difference from just getting the Stalker feat, which categorically allows you to hide when lightly obscured and you are lightly obscured from a creature with darkvision who is viewing you in darkness. Eldritch Knight may be overall far more useful for stealth at night as you can learn Control Flames to extinguish sources of illumination such as torches or lanterns and Minor Illusion or Mage-Hand to create distractions.

The 'Additional attack' is good but only puts the Gloom Stalker on-par with the number of attacks a fighter gets with Action Surge. By level 5 the fighter can use action surge to make a total of 4 attacks in a round while Gloom Stalker has potentially 3 attacks.

While one of these hits deals an additional 1d8 the limit of the additional-attack only being on the first turn in combat limits the effectiveness as the first turn in combat you may not have a chance to use the additional-attack. Action Surge has the flexibility to be used whenever needed. If you eliminate the only target in view within two shots then you don't need to use action surge and Gloom Stalker's additional attack is wasted.

Conclusion

The circumstantial limitations of Gloom Stalker limit the class too much, you need a very specific type of stealth to benefit from Umbral Sight, you also need combat to begin in a very typical formulaic way where your first turn after initiative you reliably have an opportunity to nova-strike. It also puts too much pressure on which turn is the "first turn" of combat.

A DM is liable to throw anything at a player, unlike a video game that has to follow set programming made years in advance the DM can intelligently adapt to the the player's capability, so a build that has a greater breadth of capability is better than one that's strong in only one particular area. That is why Gloom Stalker is not a particularly good option.

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