How do you load a crossbow?

Question

I know how you load a crossbow IRL but in the game you need a free hand to load them, and crossbows are two handed weapons (except the hand crossbow, but even that is sort of a two handed weapon because you need a free hand to load it so you sort of need to treat it like one).

So if you’re using two hands to hold it, then how do you load it?

Answer 1

You don't actually need a free hand to load a light or heavy crossbow.

You only need a free hand to load a one-handed weapon, not a two-handed weapon. This is clarified in newer printings of the Player's Handbook.

Both light and heavy crossbows have the Ammunition, Loading and Two-Handed properties:

• Two-handed means the weapon "requires two hands when you attack with it". This is an errata of the original, which said "requires two hands to use."
• Ammunition means you need ammunition, and drawing the ammunition is an automatic part of the attack. "You need a free hand to load a one-handed weapon", but the crossbow is two-handed. That line was added in an errata.
• Loading means you can't fire multiple times per action.

You need a free hand to load a hand crossbow, as that's a one-handed weapon.

Answer 2

From the rules:

Two-handed. This weapon requires two hands when you attack with it

(emphasis mine).

So you only need two hands when you actually make an attack with it.

I think it is safe to assume that when loading you are temporarily holding it in one hand (perhaps propped against your body or the ground) while you use the other hand to load the bolt.

Answer 3

If you look at the item description for most Crossbow-type weapons, they usually have a property called Loading, which is described like this in the Player's Handbook:

Loading. Because of the time required to load this weapon, you can fire only one piece of ammunition from it when you use an action, bonus action, or reaction to fire it, regardless of the number of attacks you can normally make.

The consequence of this is that the time and effort required to load a crossbow—the action you're looking for clarification on—is normally abstracted as simply being part of the process of firing the weapon, the consequence being that it prevents using the crossbow more than once per attack-action.

The Crossbow Expert feat eliminates the time needed to load a crossbow

Among its other features, the Crossbow Expert feat permits a user to gain the normal benefits of their Extra Attacks feature when using a Crossbow:

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.

So if you take this feat, you can ignore the cost of loading a crossbow altogether.