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Simply put, the Shadow Monk gains the ability to cast the Darkness spell, but I'm struggling to see a use for it except as concealment during an escape.

Way of the Shadow monk receives Darkness (among a few other spells) and is able to cast it as a Ki ability using 2 Ki points. The effect of the spell reads:

Magical darkness spreads from a point you choose within range to fill a 15-foot-radius sphere for the duration. The darkness spreads around corners. A creature with darkvision can’t see through this darkness, and nonmagical light can’t illuminate it.

If the point you choose is on an object you are holding or one that isn’t being worn or carried, the darkness emanates from the object and moves with it. Completely covering the source of the darkness with an opaque object, such as a bowl or a helm, blocks the darkness.

If any of this spell’s area overlaps with an area of light created by a spell of 2nd level or lower, the spell that created the light is dispelled.

Now this is useful because at level 6 the Shadow Monk gains the ability to teleport from any spot in darkness (or heavily obscured) to any other space in darkness, but I'm trying to see how this could actually be useful beyond setting up a teleport (since I would be blinded in the darkness).

Preferably I'd like a way to attack without being blinded by the darkness to make use of all the good monk features and even possibly cast it on my weapon to be a roving cloud of Darkness and punches.

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Well, if you don't mind making a pact with some powerful entity, you could get 2 levels of warlock. This will give you access to a few spells, some of which perhaps being interesting (both stats and flavor-wise) for your character. But most of all, this will give you access to 2 invocations.

One of these invocations should be Devil's Sight, which grants you the ability to see through any form of darkness, magical or otherwise, for up to 120 feet. This is more than enough to cover the 15 foot radius of the darkness spell. Cast it on your clothes, and bring terror to your enemies.

While this is a good strategy (generally favored by blade pact warlocks), it has some limitations. While under the effect of the darkness spell, your allies cannot see you. As such, any spell requiring to see the target won’t work. Keep in mind, sight is only one sense. Your location is still 100% known by allies and enemies unless you take the hide action.

These limitations also affect your enemies, however. Any attack from the outside of the sphere should have disadvantage as your enemies, even though they know your position, can't exactly see you to aim properly (blind condition). Enemies inside the darkness should also suffer from disadvantage when attacking you, unless they possess some form of blindsight or a similar ability. When you attack them, you should have advantage on the roll since you are functionally invisible for them (unseen attacker).

If both people are blind (can’t see in the darkness), you roll combat as normal since disadvantages and advantage nullify each other. Only spells and abilities that specifically say target you can see would be affected.

The biggest cost of this strategy is the fact that it requires multi-classing. While the lvl 19 and 20 abilities for monk would not really be missed (realistically, few campaigns will reach these levels), it will still set you back 2 levels in obtaining you other core monk powers. Note that doing this would get you 2 invocations, however, and that some of them can be quite interesting for a ninja-esque character:

  • Armor of Shadows (cast mage armor at will, which might be better than using your wisdom for AC if its under 16),

  • Eldritch Sight (cast detect magic at will),

  • Eyes of the Runekeeper (allows you to read anything, even languages you don't know... useful for spying!),

  • Gaze of Two Minds (share the eyes of a willing target, more spying!),

  • Mask of Many Faces (disguise self at will!), etc...

TL;DR

Sacrifice 2 monk levels and multiclass as a warlock. Gain some minor but potentially useful spellcasting, as well as the ability to see through magical darkness and one more ability of your choice!

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The Darkness spell creates a 30 foot diameter sphere of darkness anywhere within 60 feet that is line of sight of the caster. While not a physical barrier it is a barrier to vision. It provides some of the effects of total cover by blocking line of sight. Anything in the rule that relies on Line of Setting like ranged attacks, etc will be effective.

Now 30 feet means that a person within or on the far edge of the darkness is likely to be able to run through it especially with a dash action in combination with the movement. So it will only confer a advantage for a short amount of time in a moving engagement.

But not all fights are moving engagement many fights revolve around fixed points that need to be control. In which case darkness plays a similar role to smokescreens in modern warfare. A strategically located sphere of darkness that is dropped at the right moment can provide the cover need to for the party to move on a position.

Another use of darkness for a shadow monk is as a destination point. If there a nearby location in shadows the monk can use the darkness to establish a point up to 75 feet away (60 feet plus the 15 foot radius) where he can teleport into with line of sight block. The following round drop concentration and proceed on with the rest of the plan.

I suggest reading this section on Smokescreen tactics as a starting point for ideas.

Also it is not required to have a grid to be able to use darkness as a form of cover. All you need to know is whether the combat is a moving engagement or involve defending a fixed location. If it is a moving engagement then darkness will provide at best one or two rounds of cover until the combat moves away from the area in which the darkness was cast. If combat involves defending a fixed point by either side. It can be used as cover for the duration of spell shielding the defended location on one or more sides. The only position the PCs and referee has to do is decide which side are the attacks coming from.

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    \$\begingroup\$ Also, consider ttp3.dslyecxi.com/8_tactics.php, which has a whole section on using smoke for concealment. Darkness in D&D can be used for most of these purposes. \$\endgroup\$ Nov 25, 2014 at 22:19
  • \$\begingroup\$ "is likely to be able to run through it" I assume this would require the 5E equivalent of a balance check on anything other than even terrain? \$\endgroup\$
    – Lilienthal
    Nov 25, 2014 at 23:13
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    \$\begingroup\$ @Lilienthal Not per RAW, but I sure as heck would require it in my game. \$\endgroup\$ Aug 10, 2016 at 16:28
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Get the Blind Fighting fighting style

The Blind Fighting fighting style introduced in Tasha's Cauldron of Everything gives your character 10 ft. of Blindsight, allowing them to ignore the penalties they would normally incur by fighting within their Darkness spell. There are several ways of obtaining this fighting style:

  • Take the Fighting Initiate feat, also from Tasha's Cauldron of Everything
  • Take 1 level of Fighter
  • Take 2 levels of Ranger or Paladin

I would say that for most purposes Blind Fighting is weaker than the Devil's Sight invocation, mainly due to its very short range, but getting it as a feat could avoid delaying your Monk progression, or a single level of Fighter would delay the progression less than two levels of Warlock. Ranger or Paladin wouldn't delay Monk progression any less than Warlock, but could fit into your character's concept or the setting better, or their other features might be preferred.

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  • \$\begingroup\$ This is the best option for a Monk, with his high mobility, circumventing Darkness, and following the Blink Monk role-play troupe! +1 \$\endgroup\$
    – BlueMoon93
    Jul 5, 2021 at 12:24
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    \$\begingroup\$ Most importantly, this also avoids the Charisma requirement for multiclassing into Warlock, which strains an already MAD monk. \$\endgroup\$
    – qorinthian
    Apr 19, 2022 at 5:30
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With Tasha's Cauldron of Everything, you can now make a 1-level multiclass dip in a few classes, and take a feat

A new feat from TCE is useful here:

Eldritch Adept

Prerequisite: Spellcasting or Pact Magic feature

Studying occult lore, you have unlocked eldritch power within yourself: you learn one Eldritch Invocation option of your choice from the warlock class. If the invocation has a prerequisite of any kind, you can choose that invocation only if you're a warlock who meets the prerequisite.

The Devil's Sight invocation is exactly what you want, and has no prerequesites.

Devil's Sight

You can see normally in darkness, both magical and nonmagical, to a distance of 120 feet.

However, the feat itself requires you to have either Spellcasting or Pact Magic. The Shadow Monk, unfortunately, has none. So you can make a 1-level dip into Artificer, Bard, Cleric, Druid, Sorcerer, Warlock, or Wizard.

The accepted answer requires a 2-level dip in Warlock. This option requires a single-level dip and a feat. Might be useful in many cases, and you could even invest more in the other class if you think it would be useful for you (Shadow Monk and Moon Druid? who knows...)

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  • \$\begingroup\$ Brilliant! I'm playing alongside a Shadow Sorcerer who can see through their Darkness spell. I was trying to decide whether to dip into Warlock but yours is a much better solution. \$\endgroup\$
    – crantok
    Dec 3, 2022 at 21:44
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A monk with Devil's site thru 2 levels of Warlock is pretty formidable. As noted above in the OP, the darkness is NOT fixed (unlike a Silence spell, which you can also cast with Ki and is quite handy against a mage with limited movement options). You can cast it on a dagger or an arrow and throw it. You can cast it on a necklace and move about the battlefield, messing with opponents' (and of course, allies') vision. You can tuck that necklace away under your clothes and poof, no more darkness (Interacting with an item), and just as easily pull it out again to bring the globe back. You can drop said necklace to the floor, step 10 feet away, and sucker punch anyone that thinks you are standing in the middle of the globe, while watching ranged attacks come nowhere near you.

Now, take 3 levels of Warlock and you have 2 spell slots at 2nd level and the ability (should you choose the spell - and with this build you'd be a fool not to) to cast Darkness as well. Saves on the Ki point cost in the long run, but you have to balance that with the slowed Ki point progression. slots refresh on a short rest as well, so you get a couple more uses of Darkness. Personally I think that delay is worth it. You would also gain the Pact feature (personally I like Pact of the Tome for this build - gives access to some handy cantrips like Thornwhip (lets you pull some poor unsuspecting soul into your darkness from a distance) - YMMV).

One more minor point. With Devil's Sight in place, once you reach 6th level Monk and gain Shadow Step, as I read the rules there is absolutely nothing keeping you from teleporting around your darkness globe at will like a bouncing ball for the duration of the spell. That would really mess with an enemy's ability to locate you, even if it was fixed, and it isn't... Note - might want to deal with the fireball flinging mage first though...

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    \$\begingroup\$ great point about the cantrips \$\endgroup\$ Sep 22, 2016 at 20:06
  • \$\begingroup\$ +1 for suggesting extra level in Warlock to cast Darkness - makes total sense. Btw you wrote Devil's site and thru.. \$\endgroup\$
    – Thank-Glob
    Aug 4, 2023 at 7:13
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Beyond two levels in Warlock and a custom magic item, there isn't a good way to get past the limitations of Darkness. Admittedly, from a conservative roleplay perspective, I see trouble in the multiclass combination of Warlock and Monk. Putting that aside, there is a use for the spell that I haven't seen covered yet.

Beyond a sphere of advantage and evasion, or an escape technique, you can use the sphere of darkness to delay or channel enemies attacking from range. In a larger battle, you can cut off a portion of the enemies from being able to attack your party, allowing the group to focus fire on fewer targets. Through strategic division, complicated fights can be made more manageable.

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Area of effect attacks may or may not be affected. There are also forms of "vision" that this spell doesn't stop (Blindsight, etc) so if a character could get that, they could attack within the darkness without suffering the disadvantage of being "blinded".

I'm not sure a roving cloud of darkness would work, especially if the monk can't see out of it somehow (or isn't being navigated by someone else via telepathy or whatnot). I think the intent of darkness for the monk is to allow him to be able to evade if necessary or continue to attack with the hope that he can turn the "blinded" condition to his favor somehow.

As for teleporting to another area of darkness with Shadow Step, it says "you can teleport to up to 60 feet to an unoccupied space YOU CAN SEE that is also in dim light or darkness" [emphasis mine]. So by RAW a monk that casts darkness on/near himself probably can't see out of it, and thus couldn't teleport out of it either using Shadow Step. However I would probably home rule that a monk could locate his destination BEFORE casting darkness, and then could shadow step to it so long as he doesn't move.

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Instead of just dipping 2 levels into Warlock to get Devil's Sight, talk to your DM about creating magic items you might need. I understand that no DM is going to tailor-make treasure but if you give them an idea for something new and creative (for instance, a ring or amulet of Devil's Sight) they may be open to it.

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Darkness is a great tool for making the battlefield more even. If you cast Darkness on a point that you and an enemy are within the spell's radius, by Rules as Written, you will both be forced to roll straight rolls. Neither you nor your enemy can have advantage or disadvantage. You gain advantage because your enemy cannot see you, but you also gain disadvantage because you cannot see your enemy. These cancel each other out and makes it so that there is no advantage or disadvantage. This applies to your enemy as well. They have both advantage and disadvantage, which cancels each other out again.

Unfortunately there seems to be only one way of ever seeing through magical darkness, and that's by putting two levels into warlock so that you can get the Devil's Sight invocation. This, however, makes it so that you always have advantage on attacks, and that enemies always have disadvantage on attacks against you. Your enemy still can't see you, thus giving you advantage, but this time you can see your enemy, making it so that you don't have disadvantage. Your enemy still can't see you, but now you can still see him, giving him disadvantage. Enemies and allies are still rolling straight rolls against each other so long as an attacker and/or defender are in the darkness.

The reason you can do this is because of the "Heavily Obscured" property. The Heavily Obscured property states that "A creature effectively suffers from the Blinded condition when trying to see something in that area." in reference to "darkness, opaque fog, or dense foliage." The Blinded condition states that "Attack rolls against the creature have advantage, and the creatures attack rolls have disadvantage."

A helpful, and hand-made flow chart that may help with figuring out if you have advantage or disadvantage.

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    – V2Blast
    Sep 12, 2019 at 8:10
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PHB page 230 Darkness:

If the point you choose is on an object you are holding or one that isn't being worn or carried, the darkness emanates from the object and moves with it. Completely covering the source of the darkness with an opaque object, such as a bowl or a helm, blocks the darkness.

So casting it onto an object, then covering it when Darkness is not required, one can block an entryway then move with the combat and uncover the object as and when required. Lasts 10 minutes.

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