diff --git a/Essentials/src/main/java/com/earth2me/essentials/Kit.java b/Essentials/src/main/java/com/earth2me/essentials/Kit.java
index 2c9753e0428..e32ade33e33 100644
--- a/Essentials/src/main/java/com/earth2me/essentials/Kit.java
+++ b/Essentials/src/main/java/com/earth2me/essentials/Kit.java
@@ -242,10 +242,10 @@ public boolean expandItems(final User user, final List<String> items) throws Exc
 
             for (final ItemStack itemStack : leftover.values()) {
                 int spillAmount = itemStack.getAmount();
-                if (maxStackSize != 0) {
-                    itemStack.setAmount(Math.min(spillAmount, itemStack.getMaxStackSize()));
-                }
                 while (spillAmount > 0) {
+                    if (maxStackSize != 0) {
+                        itemStack.setAmount(Math.min(spillAmount, itemStack.getMaxStackSize()));
+                    }
                     user.getWorld().dropItemNaturally(user.getLocation(), itemStack);
                     spillAmount -= itemStack.getAmount();
                 }
diff --git a/Essentials/src/main/java/com/earth2me/essentials/Trade.java b/Essentials/src/main/java/com/earth2me/essentials/Trade.java
index d0dceb11114..5168e2d76ca 100644
--- a/Essentials/src/main/java/com/earth2me/essentials/Trade.java
+++ b/Essentials/src/main/java/com/earth2me/essentials/Trade.java
@@ -242,8 +242,8 @@ public Map<Integer, ItemStack> pay(final IUser user, final OverflowType type) th
                 } else {
                     for (final ItemStack itemStack : leftover.values()) {
                         int spillAmount = itemStack.getAmount();
-                        itemStack.setAmount(Math.min(spillAmount, itemStack.getMaxStackSize()));
                         while (spillAmount > 0) {
+                            itemStack.setAmount(Math.min(spillAmount, itemStack.getMaxStackSize()));
                             user.getBase().getWorld().dropItemNaturally(user.getBase().getLocation(), itemStack);
                             spillAmount -= itemStack.getAmount();
                         }