diff --git a/src/dev/w1zzrd/invtweaks/listener/StackReplaceListener.java b/src/dev/w1zzrd/invtweaks/listener/StackReplaceListener.java
index 59dea5d..0fef489 100644
--- a/src/dev/w1zzrd/invtweaks/listener/StackReplaceListener.java
+++ b/src/dev/w1zzrd/invtweaks/listener/StackReplaceListener.java
@@ -5,6 +5,8 @@ import org.bukkit.Material;
 import org.bukkit.event.EventHandler;
 import org.bukkit.event.Listener;
 import org.bukkit.event.block.BlockPlaceEvent;
+import org.bukkit.event.player.PlayerItemBreakEvent;
+import org.bukkit.inventory.EquipmentSlot;
 import org.bukkit.inventory.ItemStack;
 import org.bukkit.inventory.PlayerInventory;
 
@@ -24,21 +26,75 @@ public class StackReplaceListener implements Listener {
 
     @EventHandler
     public void onBlockPlacedEvent(final BlockPlaceEvent event) {
-        final ItemStack usedItemStack = event.getItemInHand();
+        if (findAndMoveSimilarStack(event.getItemInHand(), event.getHand(), event.getPlayer().getInventory(), CompareFunc.defaultFunc()))
+            logger.fine(LOG_PLUGIN_NAME + " Moved stack into empty hand for player " + event.getPlayer().getName());
+    }
+
+    @EventHandler
+    public void onPlayerItemBreakEvent(final PlayerItemBreakEvent event) {
+        final PlayerInventory inv = event.getPlayer().getInventory();
+        final ItemStack used = event.getBrokenItem();
+
+        final EquipmentSlot slot;
+        if (used.equals(inv.getBoots())) slot = EquipmentSlot.FEET;
+        else if (used.equals(inv.getLeggings())) slot = EquipmentSlot.LEGS;
+        else if (used.equals(inv.getChestplate())) slot = EquipmentSlot.CHEST;
+        else if (used.equals(inv.getHelmet())) slot = EquipmentSlot.HEAD;
+        else if (used.equals(inv.getItemInOffHand())) slot = EquipmentSlot.OFF_HAND;
+        else if (used.equals(inv.getItemInMainHand())) slot = EquipmentSlot.HAND;
+        else return; // No clue what broke
+
+        if (findAndMoveSimilarStack(used, slot, inv, CompareFunc.toolFunc()))
+            logger.fine(LOG_PLUGIN_NAME + " Moved tool into empty hand for player " + event.getPlayer().getName());
+    }
+
+    private boolean findAndMoveSimilarStack(
+            final ItemStack usedItemStack,
+            final EquipmentSlot target,
+            final PlayerInventory inventory,
+            final CompareFunc compareFunc) {
         if (usedItemStack.getAmount() == 1) {
-            final PlayerInventory inv = event.getPlayer().getInventory();
-            for (int i = Math.min(inv.getSize() - 1, MAX_MAIN_INV); i >= 0 ; --i) {
-                final ItemStack checkStack = inv.getItem(i);
-                if (i != inv.getHeldItemSlot() && usedItemStack.isSimilar(checkStack)) {
+            for (int i = Math.min(inventory.getSize() - 1, MAX_MAIN_INV); i >= 0 ; --i) {
+                final ItemStack checkStack = inventory.getItem(i);
+                if (i != inventory.getHeldItemSlot() && compareFunc.isSimilar(usedItemStack, checkStack)) {
                     // To prevent race-condition dupes, remove item before putting it in players hand
-                    inv.setItem(i, new ItemStack(Material.AIR, 0));
-                    inv.setItem(event.getHand(), checkStack);
+                    inventory.setItem(i, new ItemStack(Material.AIR, 0));
+                    inventory.setItem(target, checkStack);
 
-                    logger.fine(LOG_PLUGIN_NAME + " Moved stack into empty hand for player " + event.getPlayer().getName());
-
-                    break;
+                    return true;
                 }
             }
         }
+        return false;
+    }
+
+
+    /**
+     * Functional interface for determining when two item stacks are equivalent
+     *
+     * Note: The comparison should represent an equivalence relation (especially, it should be symmetric)
+     */
+    private interface CompareFunc {
+        boolean isSimilar(final ItemStack i1, final ItemStack i2);
+
+        static CompareFunc defaultFunc() { return ItemStack::isSimilar; }
+        static CompareFunc toolFunc() {
+            return (i1, i2) -> {
+                final boolean isNull1 = i1 == null;
+                final boolean isNull2 = i2 == null;
+
+                if (isNull1 || isNull2)
+                    return isNull1 == isNull2; // This should really never return true
+
+                final Material m1 = i1.getType();
+                final Material m2 = i2.getType();
+
+                // If the material name has an underscore, it probably has material type alternatives
+                if (m1.name().contains("_"))
+                    return m2.name().endsWith(m1.name().substring(i1.getType().name().lastIndexOf('_')));
+                else
+                    return m2.equals(m1);
+            };
+        }
     }
 }