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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.


1. Would shield bashing, or using the shield as a weapon, meet the requirements of the Pin Shield feat? Yes, you can use a shield as an off hand weapon for purposes of the Pin Shield feat. Like with an ordinary shield bash attack, you lose any AC bonus provided by your shield until your next action. You would also suffer any other penalties for fighting ...


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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