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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.


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 ...

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