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All halflings have the Halfling Nimbleness feature:

You can move through the space of any creature that is of a size larger than yours.

Lightfoot Halflings have the Naturally Stealthy ability:

You can attempt to hide even when you are obscured only by a creature that is at least one size larger than you.

Halflings are sized small, while Dragonborn, for instance, are medium.

A rogue has a Cunning Action:

You can take a bonus action on each of your turns in combat. This action can be used only to take the Dash, Disengage, or Hide action.

And our group has been playing with a Barbarian Dragonborn and the Lightfoot Halfling Rogue. In combat, let's say, facing a single boss, the rogue usually hits and hides behind the Dragonborn (moving through him). A stealth check is rolled against the boss's perception, and if the boss wins, he can go around the barbarian and hit the rogue. He does not trigger attacks of opportunity because he is not leaving the barbarian's melee range.

However, for the rogue to go behind the dragonborn, he should trigger an opportunity attack from the boss, right? Or can the hide action include this 5 feet move to hide behind the dragonborn? Or does the nimbleness feature prevent attacks of opportunity, since the rogue can simply stand in the dragonborn's space, only behind him? Does standing in the same space as a bigger creature prevent attacks against you because the creature shields you?

In terms of RP and realism, we've been describing this as such: the halfling is hiding in the back of the barbarian, pops out to strike, and hides back there. The idea here is to have the rogue safely out of harm's way (dumb enemies won't understand where he is, others will attack with disadvantage, and others will actually have to move to him him (unless they're grappled).

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  • \$\begingroup\$ "Does standing in the same space as a bigger creature prevent attacks against you because the creature shields you?" The DM may allow you to gain cover (+2 AC), similar to when a creature is between you and the attacker. \$\endgroup\$ – Doval Dec 23 '16 at 23:12
  • \$\begingroup\$ I don't understand 'proc an opportunity attack'. Please edit to either reword or explain what proc means. \$\endgroup\$ – Clearly Toughpick Dec 24 '16 at 9:12
  • \$\begingroup\$ @ClearlyToughpick Fixed \$\endgroup\$ – BlueMoon93 Dec 24 '16 at 14:06
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It seems the problem you're trying to solve, is how to get consistent Advantage on attacks, without provoking opportunity attacks. This depends on a number of things.

What is the boss's reach? If the boss's reach is longer than 5 ft, then you will not provoke an opportunity attack to move behind your Dragonborn friend, if he is within 5 ft of the boss.

Must you use melee attacks? Using ranged weapons in a different location would be much safer, keeping you farther from the Boss, protecting you from Area of Effect spells or abilities, and giving you Advantage consistently without having to worry about disengaging.

You're also making a few assumptions:

  1. Hiding means you are completely undetectable. This is false. He can't currently see you, and you have advantage to hit the boss, but for an intelligent creature, it's pretty obvious you're behind the Dragonborn somewhere, and he can still move around your friend to spot you. Additionally, barring the Skulker feat, attacking will reveal you. Also, simply stepping out from behind the Dragonborn will reveal you if the Boss is looking in your direction. (Also note there are no facing rules in fifth edition by default, so this is subject to GM rulings) Note this makes hiding in melee rather impractical without specialized abilities.
  2. Nimbleness means you can stand in another creature's space. You may pass through another creature's space, but you may never end your turn in another creature's space, unless they are multiple size categories larger than you.

As it stands, the Rogue does not have enough actions to Disengage, Hide, AND Attack in one turn, so he would either provoke an opportunity attack, or not be able to attack. The alternative that would allow Advantage attacks every turn, is to use a ranged weapon, and hide at a distance.

Note, if all you're concerned with is getting your sneak attack bonus, all that is required is either having advantage or an allied creature is within 5 ft of your target. Keep in mind that applies to ranged or melee attacks: so as long as the Dragonborn is next to the boss, the Rogue will still get sneak attack against it.

Unseen Attackers and Targets (Fifth Edition SRD)

Combatants often try to escape their foes’ notice by hiding, casting the invisibility spell, or lurking in darkness.

When you attack a target that you can’t see, you have disadvantage on the attack roll. This is true whether you’re guessing the target’s location or you’re targeting a creature you can hear but not see. If the target isn’t in the location you targeted, you automatically miss, but the GM typically just says that the attack missed, not whether you guessed the target’s location correctly.

When a creature can’t see you, you have advantage on attack rolls against it. If you are hidden—both unseen and unheard—when you make an attack, you give away your location when the attack hits or misses.

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  • \$\begingroup\$ Comments are not for extended discussion; this conversation has been moved to chat. \$\endgroup\$ – SevenSidedDie Dec 23 '16 at 20:38
  • \$\begingroup\$ simply stepping out from behind the Dragonborn will reveal you if the Boss is looking in your direction. He could attack from the Dragonborn's space as long as he moves out of that space afterwards; the rules say "Whether a creature is a friend or an enemy, you can't willingly end your move in its space." So if the DM rules that he counts as obscured while he's in the Dragonborn's space and the Dragonborn is next to the enemy, he could: start the turn hidden behind his friend -> move into his friend's space -> attack -> hide -> move back behind his friend. \$\endgroup\$ – Doval Dec 23 '16 at 23:10
  • \$\begingroup\$ @Doval Sage Advice disagrees with that assessment, and even if it was true, he would still provoke opportunity attacks. Whether he becomes unhidden or not in that situation is entirely up to DM judgement. \$\endgroup\$ – Randomorph Dec 24 '16 at 0:36
  • \$\begingroup\$ @Randomorph he would still provoke opportunity attacks he wouldn't provoke if he succeeds on the hide check (creatures you can't see don't provoke opportunity attacks). But I didn't account for Crawford's tweet on the subject of attacking from another creature's square, so my suggestion doesn't work regardless. Good catch. \$\endgroup\$ – Doval Dec 24 '16 at 1:53
  • \$\begingroup\$ @Doval you cannot hide from a creature that can see you, so you would have to move out of view first, before hiding. \$\endgroup\$ – Randomorph Dec 24 '16 at 1:55

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