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If my rogue attacks while hidden and dual-wielding shortswords, do I have advantage on both of my attacks (from Two-Weapon Fighting) or only on the first attack?

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    \$\begingroup\$ While I have a reasonably good idea what you're asking (and it's not about makeup [rouge vs. rogue]), your question is full of non-standard terminology - "stealthed" (do you mean Hidden?), "surprise attack" is a Bugbear ability (the rogue ability is Sneak Attack), etc. Making your question as accurate as possible is important to make sure you get the answers to what you're actually asking. \$\endgroup\$
    – T.J.L.
    Sep 7, 2018 at 18:15
  • \$\begingroup\$ What do you mean by "stealthed"? It's not a word in standard English, as it would be a past participle of stealth, which is not a verb, and therefore has no past participle. \$\endgroup\$ Sep 7, 2018 at 18:28
  • \$\begingroup\$ What do you mean by "attacks while hidden"? If you attack in melee, you approach your target, so you are no longer hidden. Do you mean attack being invisible? \$\endgroup\$
    – enkryptor
    Sep 7, 2018 at 18:46
  • \$\begingroup\$ @DerekStucki It's English. If you can word it, you can verb it. \$\endgroup\$
    – Mark Wells
    Sep 7, 2018 at 18:59

2 Answers 2

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This is similar to When attacking while invisible, when exactly does invisibility break?, and to this Sage Advice. There's also an informative Sage Advice podcast segment about stealth and attacks.

The answer is no; you reveal yourself on your first attack, unless you have a special effect that says otherwise.

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Once you have made an attack, hit or miss, the character is no longer hidden. The only exception is characters with the Skulker Feat, which both greatly increases the places a character can hide (Light Obscurement is enough) and allows the character to remain hidden after missing with a ranged attack.

That said...

In combat, most creatures stay alert for signs of danger all around, so if you come out of hiding and approach a creature, it usually sees you.

Without some extenuating circumstances, you cease to be hidden before you make a melee attack. If you're able to make the attack, then you didn't have cover from the target enough to Hide in the first place.

For a rogue in melee combat, you're more likely to get Sneak Attack from an adjacent ally than being hidden. The ally doesn't grant advantage, but it is enough to allow Sneak Attack.

Other effects can grant the Rogue Advantage - darkness when the Rogue has darkvision, other forms of obscurement when the Rogue has blindsense (which they all get at L14), and so on. If the target doesn't have similar capabilities, the Rogue may get Sneak Attack. Being hidden doesn't matter in these case.

Either way, just in case it was unclear, a Rogue only gets Sneak Attack on one attack per turn, no matter how many they take. Of course, there are ways to attack on other people's turns, which could grant Sneak Attack more than once in a round.

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  • \$\begingroup\$ I think the question here is whether the two attacks happen sequentially or at the same time. TWF requires you to make the bonus-action attack when, not "after", you take the Attack action. \$\endgroup\$
    – Mark Wells
    Sep 7, 2018 at 19:03
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    \$\begingroup\$ @MarkWells All attacks in 5E are sequential, and by use of the phrase "first attack", the question seems to be aware of this fact. \$\endgroup\$
    – T.J.L.
    Sep 7, 2018 at 19:37

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