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I am playing a shortsword-wielding monk/rogue. I know unarmed strikes do not qualify for Sneak Attack.

My question is: At later levels, can I sub in my monk damage die from Martial Arts (which will eventually be better than the 1d6 on a shortsword) and still be considered to be using the shortsword, and thus take advantage of its Finesse property to also use Sneak Attack?

I do understand that this changes the weapon die and NOT the sneak attack die.

From a roleplaying perspective, I imagine it as being that rather than simply having unarmed strikes that are more effective, I actually enhance my use of the shortsword with my martial arts because it is a monk weapon, and thus improve its intrinsic damage to match my base damage as a skilled monk.

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Yes, this is possible

Sneak attack's requirements state that:

The attack must use a finesse or a ranged weapon.

While the Martial Arts monk features changes the dice of the weapon or unarmed strike used:

You can roll a d4 in place of the normal damage of your unarmed strike or monk weapon.

Furthermore, note that the Martial Arts feature does not change the properties of the used weapon or the weapon itself. Since the shortsword is both a monk weapon and a finesse weapon it qualifies for both abilities.

Do note that the Martial Arts feature changes only the dice of the weapon used so the sneak attack dice would not be affected

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  • \$\begingroup\$ Much appreciated. I know it only amounts to a couple more potential damage but that can make all the difference in my experience. Not to be a munchkin, I just don't want to get my head smashed in by an orc with 1 hp left because I'm playing my character poorly. Thanks again =) \$\endgroup\$ – Fylvius Jun 21 '18 at 15:31
  • \$\begingroup\$ I am guessing that this would work with a dagger as well. Yes? \$\endgroup\$ – KorvinStarmast Jun 21 '18 at 18:51
  • \$\begingroup\$ Yes, this should apply to any weapon which is both a monk weapon and finesse (which looks like just those 2, unless you are a Kensei and can use rapier, scimitar, or whip as well). So dagger might actually be a better choice than a short sword (since they are cheaper and you can choose to throw them). The sword slashes and the dagger pierces. So maybe keep both around/in-hand and use whichever works best. \$\endgroup\$ – Nick Brown Jun 21 '18 at 21:08
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Yes, a shortsword is a both monk weapon and a finesse weapon

The shortsword is called out as being a valid choice as a monk weapon and thus is eligible for using the martial die for the weapon's damage rolls.

From PHB, pg. 78:

Martial Arts

At 1st level, your practice of martial arts give you mastery of combat styles that use unarmed strikes and monk weapons, which are shortswords and [...]

The shortsword is a finesse weapon, therefore is eligible for being used to trigger sneak attacks.

From PHB, pg. 96:

Sneak Attack

The attack must use a finesse [weapon] or a ranged weapon.

Both of these things can co-exist. There's nothing about the shortsword being a monk weapon that prevents it from being used for sneak attacks. The fact that the shortsword might now use a d8 or d10 for damage does not change the rogue requirement for the weapon being a finesse weapon. It's no different from using a +1 shortsword; the finesse property is the key component here.

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  • \$\begingroup\$ So is a dagger, if you want to toss that in, regarding use of monk class damage. Your call. \$\endgroup\$ – KorvinStarmast Dec 10 '18 at 3:35

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