Melee attack while hiding?

Question

I play a lightfoot halfling rogue. An ally of mine, a fighter, is in melee combat with an orc. According to the rules I can move behind the fighter, use my cunning action to hide, and if my stealth roll is higher than the orcs passive perception I can then use my shortbow to make a ranged attack with advantage. I then lose hiding due to the attack. That way I can get advantage every round on my ranged attack, and not just sneak attack, for which I don't need to hide.

Do I understand it right that this only works for ranged attacks? I can't hide if I am in melee range. And if I move from behind the fighter, I lose the hiding advantage before I can make a melee attack.

Is there any way in this situation to make a melee attack on the orc with the advantage from being hidden?

Answer 1

Unless there are other circumstances to keep you hidden, you will stop being hidden when you leave the cover provided by your fighter ally.

You could maybe use a lance or whip to attack through the fighter's square (these are the only reach weapons that I could find that are not "heavy", and so are usable by small characters without problem)

But...

It sounds like you're trying to Sneak Attack?

In which case, you don't need to be hidden.
And if your fighter ally is in melee with your target, you don't need advantage.

The rules for Sneak Attack say:

Once per turn, you can deal an extra 1d6 damage to one creature you hit with an attack if you have advantage on the attack roll. The attack must use a finesse or a ranged weapon.

You don’t need advantage on the attack roll if another enemy of the target is within 5 feet of it, that enemy isn’t incapacitated, and you don’t have disadvantage on the attack roll.

With the fighter in melee with your target, as long as you don't have disadvantage, you can either melee attack with a finesse weapon, or attack with a ranged weapon. No hiding required.

Answer 2

It's up to your DM: there is no strict prohibition on hiding within melee range

You have advantage on your attack, melee or otherwise, if your enemy can't see you (PHB 195):

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

The Hiding sidebar explicitly states that your DM can decide whether or not you can sneak up on an enemy when it's distracted (PHB 177):

However, under certain circumstances, the Dungeon Master might allow you to stay hidden as you approach a creature that is distracted, allowing you to gain advantage on an attack before you are seen.

Thus, with your DM's blessing, you could sneak up to the orc and make a melee attack from hiding.

Answer 3

You can move into the fighters space and attack from there. It's up to your DM but you have a strong argument that you remain hidden until you attack. You are allowed into an ally's square providing you don't willingly remain there.

Answer 4

Possibly, it depends on your DM for a large portion of it though.

Lightfoot halfling lets you use a medium sized creature to hide with the trait Naturally Stealthy.

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

This implies that you must move behind your ally away from the creature. The hide action let's you attempt to make a Dexterity (stealth) check against a creature's passive perception. Nothing breaking the rules as far as I can tell with this.

However in order for a lightfoot halfling to get this they need to move out of melee range and behind the ally in question that you are talking about. If your intention is to go back into melee to attack and get advantage on your melee attack then it leaves you open to AoO when you are leaving the creature's threat range to hide behind your ally. Unless the creature has 10ft reach then in that case no AoO is triggered.

After seeing this I personally as a DM would grant the creature advantage to see you since in reality you are moving 10 feet to the other side of your ally essentially in an attempt to confuse the creature to gain advantage. To me this seems to not be a traditional hide action of attempting to break line of sight and pop up somewhere else that the creature wouldn't have expected it in a stealthy manner. But with a high enough level rogue the creature's advantage on perception will most likely not be enough to hinder you successfully hiding.

As a DM you could put money down on me taking the reactions to hit your character so you would have to balance the AoO with you attempting to gain advantage.