diff --git a/src/main/java/com/sk89q/worldedit/bukkit/BukkitUtil.java b/src/main/java/com/sk89q/worldedit/bukkit/BukkitUtil.java
index 800ee10ec..75074019c 100644
--- a/src/main/java/com/sk89q/worldedit/bukkit/BukkitUtil.java
+++ b/src/main/java/com/sk89q/worldedit/bukkit/BukkitUtil.java
@@ -150,9 +150,9 @@ public class BukkitUtil {
         switch (e.getType()) {
             case EXPERIENCE_ORB:
                 return new BukkitExpOrb(toLocation(e.getLocation()), e.getUniqueId(), ((ExperienceOrb)e).getExperience());
-            /*case PAINTING: // TODO: Figure out what celticminstrel broke
+            case PAINTING:
                 Painting paint = (Painting) e;
-                return new BukkitPainting(toLocation(e.getLocation()), paint.getArt(), paint.getFacing(), e.getUniqueId());*/
+                return new BukkitPainting(toLocation(e.getLocation()), paint.getArt(), paint.getFacing(), e.getUniqueId());
             case DROPPED_ITEM:
                 return new BukkitItem(toLocation(e.getLocation()), ((Item)e).getItemStack(), e.getUniqueId());
             default:
diff --git a/src/main/java/com/sk89q/worldedit/bukkit/entity/BukkitEntity.java b/src/main/java/com/sk89q/worldedit/bukkit/entity/BukkitEntity.java
index 432db68ff..c25354796 100644
--- a/src/main/java/com/sk89q/worldedit/bukkit/entity/BukkitEntity.java
+++ b/src/main/java/com/sk89q/worldedit/bukkit/entity/BukkitEntity.java
@@ -45,6 +45,6 @@ public class BukkitEntity extends LocalEntity {
     @Override
     public boolean spawn(Location weLoc) {
         org.bukkit.Location loc = BukkitUtil.toLocation(weLoc);
-        return loc.getWorld().spawnCreature(loc, type) != null;
+        return loc.getWorld().spawn(loc, type.getEntityClass()) != null;
     }
 }
diff --git a/src/main/java/com/sk89q/worldedit/bukkit/entity/BukkitPainting.java b/src/main/java/com/sk89q/worldedit/bukkit/entity/BukkitPainting.java
index f3e5921c9..a15058f06 100644
--- a/src/main/java/com/sk89q/worldedit/bukkit/entity/BukkitPainting.java
+++ b/src/main/java/com/sk89q/worldedit/bukkit/entity/BukkitPainting.java
@@ -21,16 +21,51 @@ package com.sk89q.worldedit.bukkit.entity;
 import com.sk89q.worldedit.Location;
 import com.sk89q.worldedit.bukkit.BukkitUtil;
 import org.bukkit.Art;
+import org.bukkit.Bukkit;
 import org.bukkit.block.BlockFace;
 import org.bukkit.entity.EntityType;
 import org.bukkit.entity.Painting;
 
+import java.util.ArrayDeque;
+import java.util.Deque;
 import java.util.UUID;
 
 /**
  * @author zml2008
  */
 public class BukkitPainting extends BukkitEntity {
+    private static int spawnTask = -1;
+    private static final Deque<QueuedPaintingSpawn> spawnQueue = new ArrayDeque<QueuedPaintingSpawn>();
+
+    private class QueuedPaintingSpawn {
+        private final Location weLoc;
+
+        public QueuedPaintingSpawn(Location weLoc) {
+            this.weLoc = weLoc;
+        }
+
+        public void spawn() {
+            spawnRaw(weLoc);
+        }
+    }
+    private static class PaintingSpawnRunnable implements Runnable {
+        @Override
+        public void run() {
+            synchronized (spawnQueue) {
+                QueuedPaintingSpawn spawn;
+                while ((spawn = spawnQueue.poll()) != null) {
+                    try {
+                        spawn.spawn();
+                    } catch (Throwable t) {
+                        t.printStackTrace();
+                        continue;
+                    }
+                }
+                spawnTask = -1;
+            }
+        }
+    }
+
     private final Art art;
     private final BlockFace facingDirection;
     public BukkitPainting(Location loc, Art art, BlockFace facingDirection, UUID entityId) {
@@ -39,12 +74,29 @@ public class BukkitPainting extends BukkitEntity {
         this.facingDirection = facingDirection;
     }
 
+    /**
+     * Queue the painting to be spawned at the specified location.
+     * This operation is delayed so that the block changes that may be applied can be applied before the painting spawn is attempted.
+     *
+     * @param weLoc The WorldEdit location
+     * @return Whether the spawn as successful
+     */
     public boolean spawn(Location weLoc) {
+        synchronized (spawnQueue) {
+            spawnQueue.add(new QueuedPaintingSpawn(weLoc));
+            if (spawnTask == -1) {
+                spawnTask = Bukkit.getServer().getScheduler().scheduleSyncDelayedTask(Bukkit.getServer().getPluginManager().getPlugin("WorldEdit"), new PaintingSpawnRunnable(), 1L);
+            }
+        }
+        return true;
+    }
+
+    public boolean spawnRaw(Location weLoc) {
         org.bukkit.Location loc = BukkitUtil.toLocation(weLoc);
         Painting paint = loc.getWorld().spawn(loc, Painting.class);
         if (paint != null) {
-            paint.setFacingDirection(facingDirection);
-            paint.setArt(art);
+            paint.setFacingDirection(facingDirection, true);
+            paint.setArt(art, true);
             return true;
         }
         return false;