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As far as D&D 5E is concerned The errata'd rules prohibit it. You need a free hand to load a crossbow. In real life (yes, I know :-) It is possible to reload a hand crossbow with a shield. I've done it. It was in response to exactly this question when playing 1st edition AD&D - yes, this question is that old. The type of shield we had one with a ...


The errata added (you need a free hand to load a one-handed weapon) to the Ammunition weapon property (phb s. 146). Thus, you wont be able to carry a shield and load your weapon. As a DM myself, I would allow you to load your weapon if you posses the "war caster" feature [phb s. 170] [..] You can perform the somatic components of spells even when you have ...


No, you can't load a hand crossbow while holding a shield. The errata added a new condition to the Ammunition property: Loading a one handed weapon requires a free hand. A hand holding a shield is not a free hand, so you can't load your hand crossbow while using a shield. And since you can't load your hand crossbow, you can't make multiple attacks.


Rapid Reload feat says: If you have selected this feat for hand crossbow or light crossbow, you may fire that weapon as many times in a full attack action as you could attack if you were using a bow. Rapid Shot feat says: You can get one extra attack per round with a ranged weapon. [...] You must use the full attack action to use this feat. ...


Bows fire arrows, crossbows fire bolts. You can't use manyshot with a crossbow, though rapid shot works just fine.

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