diff --git a/paper-server/src/main/java/org/bukkit/craftbukkit/CraftWorld.java b/paper-server/src/main/java/org/bukkit/craftbukkit/CraftWorld.java
index 277c3b3dec..2ca3078d97 100644
--- a/paper-server/src/main/java/org/bukkit/craftbukkit/CraftWorld.java
+++ b/paper-server/src/main/java/org/bukkit/craftbukkit/CraftWorld.java
@@ -1083,7 +1083,11 @@ public class CraftWorld implements World {
         int blockY = block.getY();
         int blockZ = block.getZ();
         // following code is lifted from Explosion.a(boolean), and modified
-        net.minecraft.server.Block.byId[blockId].dropNaturally(this.world, blockX, blockY, blockZ, block.getData(), yield, 0);
+        int data = block.getData();
+        if (blockId == net.minecraft.server.Block.SKULL.id) {
+            data = net.minecraft.server.Block.SKULL.getDropData(this.world, blockX, blockY, blockZ);
+        }
+        net.minecraft.server.Block.byId[blockId].dropNaturally(this.world, blockX, blockY, blockZ, data, yield, 0);
         block.setType(org.bukkit.Material.AIR);
         // not sure what this does, seems to have something to do with the 'base' material of a block.
         // For example, WOODEN_STAIRS does something with WOOD in this method
diff --git a/paper-server/src/main/java/org/bukkit/craftbukkit/block/CraftBlock.java b/paper-server/src/main/java/org/bukkit/craftbukkit/block/CraftBlock.java
index c5c11fddb1..b1eb4fc6ac 100644
--- a/paper-server/src/main/java/org/bukkit/craftbukkit/block/CraftBlock.java
+++ b/paper-server/src/main/java/org/bukkit/craftbukkit/block/CraftBlock.java
@@ -342,15 +342,22 @@ public class CraftBlock implements Block {
     }
 
     public boolean breakNaturally() {
+        // Order matters here, need to drop before setting to air so skulls can get their data
         net.minecraft.server.Block block = net.minecraft.server.Block.byId[this.getTypeId()];
         byte data = getData();
+        boolean result = false;
+
+        if (block != null) {
+            if (block.id == net.minecraft.server.Block.SKULL.id) {
+                data = (byte) block.getDropData(chunk.getHandle().world, x, y, z);
+            }
+
+            block.dropNaturally(chunk.getHandle().world, x, y, z, data, 1.0F, 0);
+            result = true;
+        }
 
         setTypeId(Material.AIR.getId());
-        if (block != null) {
-            block.dropNaturally(chunk.getHandle().world, x, y, z, data, 1.0F, 0);
-            return true;
-        }
-        return false;
+        return result;
     }
 
     public boolean breakNaturally(ItemStack item) {