diff --git a/paper-api/src/main/java/org/bukkit/entity/HumanEntity.java b/paper-api/src/main/java/org/bukkit/entity/HumanEntity.java
index 188c8e27d7..b1d1b759af 100644
--- a/paper-api/src/main/java/org/bukkit/entity/HumanEntity.java
+++ b/paper-api/src/main/java/org/bukkit/entity/HumanEntity.java
@@ -706,6 +706,107 @@ public interface HumanEntity extends LivingEntity, AnimalTamer, InventoryHolder
      */
     public boolean dropItem(boolean dropAll);
 
+    // Paper start - Extend HumanEntity#dropItem API
+    /**
+     * Makes the entity drop an item from their inventory.
+     * <br>
+     * This method calls {@link HumanEntity#dropItem(int slot)}
+     * with the first {@link ItemStack} occurrence in the inventory
+     *
+     * @param itemStack The ItemStack to drop
+     * @return The dropped item, or null if the action was unsuccessful
+     */
+    public @Nullable Item dropItem(final @NotNull ItemStack itemStack);
+
+    /**
+     * Makes the entity drop an item from their inventory.
+     * <br>
+     * This method calls {@link HumanEntity#dropItem(int slot, java.util.UUID thrower)}
+     * with the first {@link ItemStack} occurrence in the inventory
+     *
+     * @param itemStack The ItemStack to drop from their inventory
+     * @param thrower   The {@link java.util.UUID} to set the resulting {@link Item}'s thrower to
+     * @return The dropped item, or null if the action was unsuccessful
+     */
+    public @Nullable Item dropItem(final @NotNull ItemStack itemStack, final @Nullable java.util.UUID thrower);
+
+    /**
+     * Makes the entity drop an item from their inventory based on the specified ItemStack.
+     * <br>
+     * This method calls {@link HumanEntity#dropItem(int slot, java.util.UUID thrower, boolean throwRandomly)}
+     * with the first {@link ItemStack} occurrence in the inventory
+     *
+     * @param itemStack     The ItemStack to drop
+     * @param thrower       The {@link java.util.UUID} to set the resulting {@link Item}'s thrower to
+     * @param throwRandomly Whether the item should disperse randomly.
+     *                      This means that instead of the item being dropped where the player is currently looking,
+     *                      it instead throws it in any direction, similar to how items drop after a player's death.
+     * @return The dropped item, or null if the action was unsuccessful
+     */
+    public @Nullable Item dropItem(final @NotNull ItemStack itemStack, final @Nullable java.util.UUID thrower, final boolean throwRandomly);
+
+    /**
+     * Makes the entity drop an item from their inventory based on the slot.
+     *
+     * @param slot The slot to drop
+     * @return The dropped item, or null if the action was unsuccessful
+     * @throws IndexOutOfBoundsException If the slot is negative or bigger than the player's inventory
+     */
+    public @Nullable Item dropItem(final int slot);
+
+    /**
+     * Makes the entity drop an item from their inventory based on the slot.
+     *
+     * @param slot    The slot to drop
+     * @param thrower The {@link java.util.UUID} to set the resulting {@link Item}'s thrower to
+     * @return The dropped item, or null if the action was unsuccessful
+     * @throws IndexOutOfBoundsException If the slot is negative or bigger than the player's inventory
+     */
+    public @Nullable Item dropItem(final int slot, final @Nullable java.util.UUID thrower);
+
+    /**
+     * Makes the entity drop an item from their inventory based on the slot.
+     *
+     * @param slot          The slot to drop
+     * @param thrower       The {@link java.util.UUID} to set the resulting {@link Item}'s thrower to
+     * @param throwRandomly Whether the item should disperse randomly.
+     *                      This means that instead of the item being dropped where the player is currently looking,
+     *                      it instead throws it in any direction, similar to how items drop after a player's death.
+     * @return The dropped item entity, or null if the action was unsuccessful
+     * @throws IndexOutOfBoundsException If the slot is negative or bigger than the player's inventory
+     */
+    public @Nullable Item dropItem(final int slot, final @Nullable java.util.UUID thrower, final boolean throwRandomly);
+
+    /**
+     * Makes the entity drop an item from their inventory based on the {@link org.bukkit.inventory.EquipmentSlot}
+     *
+     * @param slot The equipment slot to drop
+     * @return The dropped item entity, or null if the action was unsuccessful
+     */
+    public @Nullable Item dropItem(final @NotNull org.bukkit.inventory.EquipmentSlot slot);
+
+    /**
+     * Makes the entity drop an item from their inventory based on the {@link org.bukkit.inventory.EquipmentSlot}
+     *
+     * @param slot    The equipment slot to drop
+     * @param thrower The {@link java.util.UUID} to set the resulting {@link Item}'s thrower to
+     * @return The dropped item entity, or null if the action was unsuccessful
+     */
+    public @Nullable Item dropItem(final @NotNull org.bukkit.inventory.EquipmentSlot slot, final @Nullable java.util.UUID thrower);
+
+    /**
+     * Makes the player drop an item from their inventory based on the equipment slot.
+     *
+     * @param slot          The equipment slot to drop
+     * @param thrower       The {@link java.util.UUID} to set the resulting {@link Item}'s thrower to
+     * @param throwRandomly Whether the item should disperse randomly.
+     *                      This means that instead of the item being dropped where the player is currently looking,
+     *                      it instead throws it in any direction, similar to how items drop after a player's death.
+     * @return The dropped item entity, or null if the action was unsuccessful
+     */
+    public @Nullable Item dropItem(final @NotNull org.bukkit.inventory.EquipmentSlot slot, final @Nullable java.util.UUID thrower, final boolean throwRandomly);
+    // Paper end
+
     /**
      * Gets the players current exhaustion level.
      * <p>
diff --git a/paper-server/src/main/java/org/bukkit/craftbukkit/entity/CraftHumanEntity.java b/paper-server/src/main/java/org/bukkit/craftbukkit/entity/CraftHumanEntity.java
index e345cdbfab..3b225dc19e 100644
--- a/paper-server/src/main/java/org/bukkit/craftbukkit/entity/CraftHumanEntity.java
+++ b/paper-server/src/main/java/org/bukkit/craftbukkit/entity/CraftHumanEntity.java
@@ -66,6 +66,8 @@ import org.bukkit.permissions.Permission;
 import org.bukkit.permissions.PermissionAttachment;
 import org.bukkit.permissions.PermissionAttachmentInfo;
 import org.bukkit.plugin.Plugin;
+import org.jetbrains.annotations.NotNull;  // Paper - Extend HumanEntity#dropItem API
+import org.jetbrains.annotations.Nullable; // Paper - Extend HumanEntity#dropItem API
 
 public class CraftHumanEntity extends CraftLivingEntity implements HumanEntity {
     private CraftInventoryPlayer inventory;
@@ -801,6 +803,86 @@ public class CraftHumanEntity extends CraftLivingEntity implements HumanEntity {
         // Paper end - Fix HumanEntity#drop not updating the client inv
     }
 
+    // Paper start - Extend HumanEntity#dropItem API
+    @Override
+    public @Nullable org.bukkit.entity.Item dropItem(final @NotNull ItemStack itemStack) {
+        return this.dropItem(itemStack, null, false);
+    }
+
+    @Override
+    public @Nullable org.bukkit.entity.Item dropItem(final @NotNull ItemStack itemStack, final @Nullable java.util.UUID thrower) {
+        return this.dropItem(itemStack, thrower, false);
+    }
+
+    @Override
+    public @Nullable org.bukkit.entity.Item dropItem(final @NotNull ItemStack itemStack, final @Nullable java.util.UUID thrower, final boolean throwRandomly) {
+        final int slot = this.inventory.first(itemStack);
+        if (slot == -1) {
+            return null;
+        }
+
+        return this.dropItem(slot, thrower, throwRandomly);
+    }
+
+    @Override
+    public @Nullable org.bukkit.entity.Item dropItem(final int slot) {
+        return this.dropItem(slot, null, false);
+    }
+
+    @Override
+    public @Nullable org.bukkit.entity.Item dropItem(final int slot, final @Nullable java.util.UUID thrower) {
+        return this.dropItem(slot, thrower, false);
+    }
+
+    @Override
+    public @Nullable org.bukkit.entity.Item dropItem(final int slot, final @Nullable java.util.UUID thrower, final boolean throwRandomly) {
+        // Make sure the slot is in bounds
+        if (slot < 0 || this.inventory.getSize() <= slot) {
+            throw new IndexOutOfBoundsException("Slot " + slot + " out of range for inventory of size " + this.inventory.getSize());
+        }
+
+        final ItemStack stack = this.inventory.getItem(slot);
+        final org.bukkit.entity.Item itemEntity = dropItemRaw(stack, thrower, throwRandomly);
+
+        this.inventory.setItem(slot, null);
+        return itemEntity;
+    }
+
+    @Override
+    public @Nullable org.bukkit.entity.Item dropItem(final @NotNull org.bukkit.inventory.EquipmentSlot slot) {
+        return dropItem(slot, null, false);
+    }
+
+    @Override
+    public @Nullable org.bukkit.entity.Item dropItem(final @NotNull org.bukkit.inventory.EquipmentSlot slot, final @Nullable java.util.UUID thrower) {
+        return dropItem(slot, thrower, false);
+    }
+
+    @Override
+    public @Nullable org.bukkit.entity.Item dropItem(final @NotNull org.bukkit.inventory.EquipmentSlot slot, final @Nullable java.util.UUID thrower, final boolean throwRandomly) {
+        final ItemStack stack = this.inventory.getItem(slot);
+        final org.bukkit.entity.Item itemEntity = dropItemRaw(stack, thrower, throwRandomly);
+
+        this.inventory.setItem(slot, null);
+        return itemEntity;
+    }
+
+    private org.bukkit.entity.Item dropItemRaw(final ItemStack is, final @Nullable java.util.UUID thrower, final boolean throwRandomly) {
+        if (is == null || is.getType() == Material.AIR) {
+            return null;
+        }
+
+        final net.minecraft.world.entity.item.ItemEntity droppedEntity = this.getHandle().drop(CraftItemStack.asNMSCopy(is), throwRandomly);
+        if (droppedEntity == null) {
+            return null;
+        }
+
+        droppedEntity.thrower = thrower;
+        return (org.bukkit.entity.Item) droppedEntity.getBukkitEntity();
+    }
+    // Paper end
+
+
     @Override
     public float getExhaustion() {
         return this.getHandle().getFoodData().exhaustionLevel;