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Specifically, I want to attack 4 times with Eldritch Blast as a 17th level Warlock. What is the easiest and cheapest way to gain advantage on all 4 attacks?

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    \$\begingroup\$ Incidentally, I'm pretty sure Enhance Ability doesn't grant advantage on attacks - attacks are not ability checks. \$\endgroup\$ – Miniman Sep 19 '14 at 4:29
  • \$\begingroup\$ I am confuse. How on earth are you supposed to get four attacks as a Warlock? Did they have Extra Attacks in the playtest? \$\endgroup\$ – trekkieyk Sep 26 '15 at 2:51
  • \$\begingroup\$ I was totally looking at the class, and forgot to look at the spell description. \$\endgroup\$ – trekkieyk Sep 26 '15 at 17:45
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    \$\begingroup\$ You aren't using Eldritch Blast 4 times at Level 17. A single cast of Eldritch Blast produces 4 beams, each with a separate attack roll. \$\endgroup\$ – Drunk Cynic Jun 12 '16 at 16:06
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TL;DR
Play a drow warlock, and take the eldritch invocation Devil's Sight. Faerie Fire grants advantage against any creature illuminated by it. Devil's Sight allows you to see in magical darkness, and the Darkness spell grants advantage.


Other ways of gaining advantage:

Being Unseen
From PH 194:

When a creature can't see you, you have advantage on attack rolls against it

Conditions
If any of these apply to your target then you will have advantage:

  • Blinded
  • Paralyzed
  • Petrified
  • Prone (and attacker within 5')
  • Restrained
  • Stunned
  • Unconscious

Class Abilities

  • Cleric with Trickery domain. At level 2 they can use Channel Divinity to create an illusionary double. If both you and your double are within 5' of the creature then you have advantage.
  • Paladin with Oath of Vengance. At level 3 they can use Channel Divinity for the Vow of Enmity that gives them advantage on attack rolls against 1 creature
  • Rogue with Assassin archetype. At level 3 they gain the Assassinate ability and have advantage on any attack rolls against creatures that haven't taken a turn in the combat yet

Spells
Any spell that inflicts one of the earlier conditions or causes you to become unseen (eg - Blindness/Deafness, Greater Invisiblitiy) will give you advantage. These spells specifically grant advantage:

  • Faerie Fire
  • Foresight
  • Otto's Irresistable Dance
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  • \$\begingroup\$ I think you are missing one more. Under class abilities of Monk under Monastic Traditions under Way of the Shadow at 6th level you get Shadow step and that gives you advantage if you use shadow step and use a melee attack on the same turn after the teleport. \$\endgroup\$ – Progredi Jul 24 '15 at 23:39
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    \$\begingroup\$ Nice list, but one problem- Eldritch Blast is a ranged attack, so if you do it from 5' away the disadvantage will cancel out the advantage from Duplicity. \$\endgroup\$ – SirTechSpec Jun 12 '16 at 13:26
  • \$\begingroup\$ You can't cast Faerie Fire and Darkness at the same time; both take Concentration. \$\endgroup\$ – Drunk Cynic Jun 12 '16 at 16:10
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    \$\begingroup\$ @Progredi You can't have 6 levels of Monk and 17 levels of Warlock, and Eldritch Blast isn't a melee attack. \$\endgroup\$ – T.J.L. Jun 13 '16 at 12:41
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    \$\begingroup\$ @briddums Yes; suggest you edit the opening paragraph to firmly state that it is "Faerie Fire and Pact with Archefey" or "Darkness and Devil's Sight." \$\endgroup\$ – Drunk Cynic Jun 15 '16 at 2:41
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The best way to do this - Have an ally cast Greater Invisibility on you. An Invisible attacker has advantage automatically, and with Greater Invisibility you can attack without losing the Invisibility. This will grant you advantage for as long as the spell persists.

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  • \$\begingroup\$ Is that assuming your target does not have blind sight or tremor sense? \$\endgroup\$ – Premier Bromanov Jun 20 '16 at 14:09
  • \$\begingroup\$ By a strict RAW reading of the Invisible condition, it doesn't actually matter whether the target can see through Invisibility or not. I can't guarantee your DM won't throw a book at your head if you tell him this, though. \$\endgroup\$ – Miniman Jun 20 '16 at 14:13
  • \$\begingroup\$ @Miniman How? By a strict reading, the invisible condition is negated by a "special sense," such as tremorsense, blindsight, or truesight. \$\endgroup\$ – Drunk Cynic Jun 20 '16 at 14:55
  • \$\begingroup\$ "An invisible creature is impossible to see without the aid of magic or a special sense." Then, in an entirely separate dot point, with no connection drawn between the two: "Attack rolls against the creature have disadvantage, and the creature's attack rolls have advantage." \$\endgroup\$ – Miniman Jun 20 '16 at 15:03
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    \$\begingroup\$ @Miniman I'm sorry but I don't see how it makes logical sense to be able to negate invisibility but not its effects. \$\endgroup\$ – Premier Bromanov Jun 20 '16 at 17:38
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Ways to get advantage

  • Use inspiration
  • Have stealth
  • DM rules you have it because of something situational
  • target is suffering from a condition that grants advantage

Only reliable option: On a previous turn (yours or a party member's) someone will have needed to inflict a status like restrained on the target.

The only reliable way to have advantage for that many attacks is to be making them against a target that is restrained or paralyzed.

I find it highly unlikely that even if 4 members of the party had inspiration that they would give it up to you for the nova round you are trying to build. Stealth + your own point of inspiration is still only 2 attacks. DM fiat is too situational to rely on and even still would probably only net you 1 use of advantage.

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  • \$\begingroup\$ Flanking exists in 5e right? not sure the exact rules on it as I dont have my book near by. but if the enemy was flanked by the allies wouldnt all the attacks have advantage? \$\endgroup\$ – MC_Hambone Sep 18 '14 at 19:21
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    \$\begingroup\$ Flanking doesn't really exist anymore. It's been reduced to "a rogue can sneak attack if an ally is beside the creature" \$\endgroup\$ – briddums Sep 18 '14 at 19:54
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The cheapest method is to take the Devils Sight Invocation combined with a darkness creating spell, like Darkness or Hunger of Hadar.

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If this is all you want your high level warlock to do is get advantage on eb - take 13 levels rogue(archane trickster) and use free action to slap your target with your mage hand to give you 4 eb's with advantage.

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  • \$\begingroup\$ How exactly are you supposed to have 13 levels of rogue when you're a 17th-level warlock? \$\endgroup\$ – Dan Henderson Jun 13 '16 at 20:56
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    \$\begingroup\$ @DanHenderson If you're a 13/4 Rogue/Warlock, you're character level is 17, giving you 4 beams for Eldritch Blast. \$\endgroup\$ – Drunk Cynic Jun 14 '16 at 0:56
  • \$\begingroup\$ @DrunkCynic ah, you're right, I missed that attribute of cantrips. \$\endgroup\$ – Dan Henderson Jun 14 '16 at 14:42
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A familiar can 'Help' you granting advantage on your first attack roll. The Owl seems the best at this.

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    \$\begingroup\$ The Help action only gives advantage for the first attack. \$\endgroup\$ – András Sep 21 '14 at 18:31
  • \$\begingroup\$ Yeah, I double checked before reading your comment but after you posted. \$\endgroup\$ – Eric Sep 21 '14 at 18:38

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