Does a Melee attack with a Hand Crossbow allow you to make another Hand Crossbow attack with your bonus action using the Crossbow Expert Feat?

Question

A Human Fighter takes the Crossbow Expert Feat at level 1. In combat, he runs out of ammunition before he runs out of enemies. Could he make a Melee attack with his Hand Crossbow, (using it as an improvised weapon), and then have the option of using his bonus action to do the same thing again?

for reference, here is the Crossbow Expert Feat from the PHB

Thanks to extensive practice with the crossbow, you gain the following benefits: You ignore the loading quality of crossbows with which you are proficient. Being within 5 feet of a hostile creature doesn’t impose disadvantage on your ranged attack rolls. 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.

Answer 1

Yes, Crossbow Expert allows you to pistol whip with a hand crossbow and then do the same thing as a bonus action

The first part of this interaction hinges on whether or not an improvised weapon is considered to be a weapon for the purposes of rules and features that depend on you doing something with a weapon. We already have a great question and answer about that here: Are Improvised Weapons used in melee actually melee weapons?

As NautArch's answer clarifies, improvised weapons don't strictly get to call themselves melee weapons or ranged weapons, since they exist outside that classification, and therefore aren't compatible with rules that refer specifically to melee weapons or ranged weapons - but they are still weapons at the moment you use them to attack, and luckily Crossbow Expert only specifies an attack with a one-handed weapon, not a melee weapon or a ranged weapon.

It seems obvious therefore that an improvised weapon wielded in one hand - lacking as it does the two-handed property - is a one-handed weapon, and so therefore taking the Attack action and making an attack with it satisfies the criteria which allows you to make a bonus action attack with a hand crossbow. That the hand crossbow is itself the improvised weapon you used in the first attack doesn't matter, since it's well established that shooting a hand crossbow also qualifies to let you make a bonus attack with the same hand crossbow.

Having established we get to make the bonus attack, the second question is whether or not the bonus attack could be used to make another melee attack with the hand crossbow as improvised weapon rather than having to shoot the crossbow normally.

Fortunately the language used in the feat doesn't seem to rule this out at all; it doesn't specify that you "shoot" the hand crossbow, or specify that you must use the crossbow to make a ranged attack - it simply allows that you can make an attack with the hand crossbow. The natural understanding of using the crossbow as an improvised club is that you are making an attack with the crossbow, even if it's not the one the crossbow was designed to make, so there is no conflict between the text of the rules and the action you want to undertake here.

TL;DR yes - attacking with a one-handed improvised weapon satisfies the criteria for Crossbow Expert's bonus attack, and the rules text for the bonus attack doesn't exclude using a hand crossbow as an improvised weapon in melee instead of shooting it normally.

Answer 2

Yes, he may use his bonus action to make a Melee attack when he makes a Melee attack with his Hand Crossbow.

The snippet that you cite already contains the relevant information:

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.

Using an improvised Melee attack doesn't change the nature of the action. The feat provides you with multiple bonuses, and the language doesn't indicate that the attack has to be ranged - it would mention it.

Answer 3

By book RAW yes, by RAI / Sage Advice, No

@Carcer answer cover the question when reading the book.

However there's a published sage advice covering this feat, where you can read: (emphasis mine)

To dig deeper into this point, take a look at the following sentence in the definition of the ammunition property: “Drawing the ammunition from a quiver, case, or other container is part of the attack.” The sentence tells us two important things. First, you’re assumed to be drawing—that is, extracting with your hand—the ammunition from a container. Second, the act of drawing the ammunition is included in the attack and therefore doesn’t require its own action and doesn’t use up your free interaction with an object on your turn.

What does that all mean for a hand crossbow? It means Crossbow Expert makes it possible to fire a hand crossbow more than once with a feature like Extra Attack, provided that you have enough ammunition and you have a hand free to load it for each shot.

Does Crossbow Expert let you fire a hand crossbow and then fire it again as a bonus action? It does! Take a look at the feat’s third benefit. It says you can attack with a hand crossbow as a bonus action when you use the Attack action to attack with a one-handed weapon. A hand crossbow is a one-handed weapon, so it can, indeed, be used for both attacks, assuming you have a hand free to load the hand crossbow between the two attacks.

This makes clear that the bonus attack is intended to be the "normal" use of the crossbow, I.E. as a ranged weapon, loading ammunition.