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Simply put, the Shadow Monk gains the ability to cast Darkness, 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 w orn 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 feet 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 line of sight that they would like to cast on you simply cannot work. Healing you might be problematic, as it requires your allies to be able to touch you. They might know that you are smack in the middle of that sphere of pure black darkness but, once they get inside, it's suddenly not so easy to find you anymore.

These limitations also affect your enemies, however. Any attack from the outside of the sphere should have disadvantage as your enemies, even if they can approximate your position, can't exactly see you to aim properly. 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.

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\$ – Kyle Willey Nov 25 '14 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 '14 at 23:13
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    \$\begingroup\$ @Lilienthal Not per RAW, but I sure as heck would require it in my game. \$\endgroup\$ – Will Rhodes Aug 10 '16 at 16:28
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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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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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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\$ – Joshua Aslan Smith Sep 22 '16 at 20:06
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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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Well darkness allows only you to see through it, if you cast it in their area you could destroy them without endangering your self, unless it's a shadow elemental, bad idea in that case.

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  • \$\begingroup\$ Destroy and endanger are inexact terms. An example of an ideal scenario (you have already presented a case against your argument) would be appreciated. For example: "a party of ___ PCs level ___ is in a combat encounter with ____, if the party had a shadow monk who could cast darkness then beneficial result ___ would happen." \$\endgroup\$ – name moniker May 7 '16 at 20:21
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    \$\begingroup\$ Darkness doesn't allow you to see through it - that's the whole point of this question. \$\endgroup\$ – Miniman May 7 '16 at 23:02

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