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The Crossbow Expert feat (PHB, pg. 165) says:

When you use the Attack action and attack with a one-handed weapon, you can use a bonus action to attack with a hand crossbow you are holding.

The description of the Versatile property (PHB, pg. 147) says:

Versatile. This weapon can be used with one or two hands. A damage value in parentheses appears with the property — the damage when the weapon is used with two hands to make a melee attack.

If I have a level 4 Ranger (and hence does not have Extra Attack) with the Crossbow Expert feat, and he only has a longsword in his hand at the start of his turn, can he take the Attack action and use it Versatile (i.e. with two hands), then let go of the longsword with one hand (sword still held in his other hand), use his free object interaction to draw a loaded hand crossbow (with his now-free hand) and fire it with his bonus action due to the above quote?

Note that this is not a hypothetical situation; I did this last night (although only once) during the game of an inexperienced DM, and I want to know if I'm gaining an unfair not-RAW advantage by doing this, and if so, stop doing it and let them know that I shouldn't be able to do this.

So there are two questions here, but I believe that they are inseparable*:

  • The longsword is a one-handed weapon, but does using it Versatile mean that it is considered a two-handed weapon for that attack and thus disallow the above sequence of events?
  • Given that I don't have the hand crossbow in my hand when I make the original attack with the longsword, does that disallow the above sequence because the feat specifies "a hand crossbow you are holding", even though I am holding it after the attack but before my bonus action?

* The reason I think these questions are inseparable is that, if I were to ask the "versatile" question on it's own, the "you are holding" part might be the only reason it doesn't work, but to ask that bit on its own has the obvious answer "why don't you just draw it before you make your attack?" and the answer is that I'm trying to use the sword Versatile first. Hence, these questions don't make sense separately, and I suspect they can both be answered at the same time with one concise answer.

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You need to be holding the Hand Crossbow when you take the Attack action

The wording on the Crossbow Expert feat that you already quote:

When you use the Attack action and attack with a one-handed weapon, you can use a bonus action to attack with a hand crossbow you are holding.

This is very similar to the wording on the Two-weapon fighting rules:

When you take the Attack action and attack with a light melee weapon that you’re holding in one hand, you can use a Bonus Action to attack with a different light melee weapon that you’re holding in the other hand.

The requirements on holding the weapon are generally understood to mean that you have to already be holding the second weapon when making the Attack action. (See this related answer for details). While this is about two weapon fighting the wording is close enough that we can assume that you are also supposed to be holding the hand crossbow for the Crossbow Expert feat.

Using a Versatile weapon with two hands is not a problem by itself

Using a weapon with the Versatile property is not the same thing as using a two-handed weapon. A Versatile weapon is still considered a one-handed weapon.

See this tweet from Jeremy Crawford which explains that Versatile is different from being a two-handed weapon:

Pedro Coelho @rockhollyrabbit · 13 Feb 2017
@JeremyECrawford for the Hexblade pact's Hex Warrior does the 2handed thing include versatile weapons wielded 2 handed or just pure 2handed?

Jeremy Crawford @JeremyECrawford · 13 Feb 2017
Two-handed and versatile are two different weapon properties (PH, 146–7). A reference to one is not a reference to the other: A ≠ B.

What this means is that if you somehow found a way to attack with the longsword with both hands while still holding the hand crossbow in another hand (I am not seeing a way to do this barring something strange like having 3 hands), you would theoretically qualify for the Crossbow Expert feat as normal.

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  • \$\begingroup\$ The typical fantasy trope is arm brace mounted light crossbow. Though I do not know if this construction would be legal under the rules outside of GM fiat. \$\endgroup\$ – Winterborne Oct 4 '18 at 16:45
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    \$\begingroup\$ @Winterborne That may be a solution but I am unaware of any rules for such a setup in dnd-5e \$\endgroup\$ – Sdjz Oct 4 '18 at 16:46
  • \$\begingroup\$ Also might not count as "holding". \$\endgroup\$ – Ben Barden Oct 5 '18 at 14:13
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No, this would not work

Look at the wording on the Crossbow Expert feat:

When you use the Attack action and attack with a one-handed weapon, you can use a bonus action to attack with a hand crossbow you are holding.

The feat states that the crossbow you have must be held beforehand. Hence why it says "You are holding" and not just "attack with a hand crossbow" period.

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    \$\begingroup\$ using a weapon with one hand or using a weapon with the one handed propery are differant, as seen in this question (even though it is about 2 handed but same apllies) \$\endgroup\$ – darnok Oct 4 '18 at 10:34
  • \$\begingroup\$ This would be a better answer without the uncertainty. \$\endgroup\$ – T.J.L. Oct 4 '18 at 15:33
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    \$\begingroup\$ @Ghiojo I would say "the feat states that the..." It is not implicit but explicit \$\endgroup\$ – David Coffron Oct 4 '18 at 15:46
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You can do this if you have a 3rd arm

The bonus action you use has to be in direct succession to the other attack so you don't have the option to drop and draw before you take the bonus action mentioned. However if you have a third arm (you didn't say which race you were, you might have a lot of arms), you can draw your crossbow with your third arm before attacking with your sword. That way when you attack with the sword, you will also be holding a crossbow and you can take your bonus action as you described.

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  • \$\begingroup\$ With the new Loxodon race this might be possible (elephant people with a trunk that acts as an arm) but I believe it specifically says the trunk can't use weapons. Apart from that, if you're playing a homebrew race with 3+ arms that are fully functional then I agree. I'd still double check with the DM of course. \$\endgroup\$ – Captain Man Oct 4 '18 at 15:05
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    \$\begingroup\$ There are no official races with 3 arms. The Loxodon is Unearthed Arcana and it also doesn't state that the trunk can be to wield a weapon (just that it can lift and carry and can do some undefined delicate manipulation.) \$\endgroup\$ – NautArch Oct 4 '18 at 15:14
  • \$\begingroup\$ Not an RPG player myself, but the rule only says that you have to be holding a crossbow. It doesn't say that the bonus attack has to be done with the same "arm" that is holding it. Would it be allowed to switch the crossbow from your trunk to your hand for the bonus attack? \$\endgroup\$ – walen Oct 5 '18 at 8:28

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