diff --git a/core/src/main/java/com/nisovin/magicspells/spells/MenuSpell.java b/core/src/main/java/com/nisovin/magicspells/spells/MenuSpell.java
index d2683161e..0a7ccaaec 100644
--- a/core/src/main/java/com/nisovin/magicspells/spells/MenuSpell.java
+++ b/core/src/main/java/com/nisovin/magicspells/spells/MenuSpell.java
@@ -133,6 +133,14 @@ public MenuSpell(MagicConfig config, String spellName) {
 			option.power = getConfigFloat(path + "power", 1);
 			option.modifierList = getConfigStringList(path + "modifiers", null);
 			option.stayOpen = getConfigBoolean(path + "stay-open", false);
+
+			String modeString = getConfigString(path + "sort-mode", "none");
+			option.sortMode = Util.enumValueSafe(SortMode.class, modeString);
+			if (option.sortMode == null) {
+				MagicSpells.error("MenuSpell '" + internalName + "' has an invalid 'sort-mode' defined for '" + optionName + "': '" + modeString + "'. Falling back to 'none'.");
+				option.sortMode = SortMode.NONE;
+			}
+
 			options.put(optionName, option);
 		}
 		size = (int) Math.ceil((maxSlot + 1) / 9.0) * 9;
@@ -293,9 +301,28 @@ private void applyOptionsToInventory(Player opener, MenuInventory menu) {
 			} else quantity = (int) Math.round(variable.getValue(opener));
 			item.setAmount(quantity);
 
-			// Set item for all defined slots.
-			for (int slot : option.slots) {
-				if (inv.getItem(slot) == null) inv.setItem(slot, item);
+			// Set item for the defined slots based on the configured fill behavior.
+			switch (option.sortMode) {
+				case FIRST -> {
+					for (int slot : option.slots) {
+						if (inv.getItem(slot) != null) continue;
+						inv.setItem(slot, item);
+						break;
+					}
+				}
+				case LAST -> {
+					for (int index = option.slots.size() - 1; index >= 0; index--) {
+						int slot = option.slots.get(index);
+						if (inv.getItem(slot) != null) continue;
+						inv.setItem(slot, item);
+						break;
+					}
+				}
+				case NONE -> {
+					for (int slot : option.slots) {
+						if (inv.getItem(slot) == null) inv.setItem(slot, item);
+					}
+				}
 			}
 		}
 		// Fill inventory.
@@ -434,6 +461,12 @@ private enum PostClickState {
 		IGNORE
 	}
 
+	private enum SortMode {
+		NONE,
+		FIRST,
+		LAST
+	}
+
 	private static class MenuOption {
 
 		private String menuOptionName;
@@ -456,6 +489,7 @@ private static class MenuOption {
 		private float power;
 		private List<String> modifierList;
 		private ModifierSet menuOptionModifiers;
+		private SortMode sortMode;
 		private boolean stayOpen;
 
 	}
diff --git a/core/src/main/java/com/nisovin/magicspells/spells/targeted/MobGoalEditSpell.java b/core/src/main/java/com/nisovin/magicspells/spells/targeted/MobGoalEditSpell.java
index 2e93a36d6..7c1b6007c 100644
--- a/core/src/main/java/com/nisovin/magicspells/spells/targeted/MobGoalEditSpell.java
+++ b/core/src/main/java/com/nisovin/magicspells/spells/targeted/MobGoalEditSpell.java
@@ -38,7 +38,7 @@ public MobGoalEditSpell(MagicConfig config, String spellName) {
 		List<String> removeTypeStrings = getConfigStringList("remove-types", null);
 		if (removeTypeStrings != null) {
 			for (String string : removeTypeStrings) {
-				GoalType type = Util.enumValueSafe(GoalType.class, string.toUpperCase());
+				GoalType type = Util.enumValueSafe(GoalType.class, string);
 				if (type == null) {
 					MagicSpells.error("MobGoalEditSpell '" + internalName + "' lists an invalid value in 'remove-types': " + string);
 					continue;
diff --git a/core/src/main/java/com/nisovin/magicspells/util/Util.java b/core/src/main/java/com/nisovin/magicspells/util/Util.java
index ae07fe927..ba3bdfbb4 100644
--- a/core/src/main/java/com/nisovin/magicspells/util/Util.java
+++ b/core/src/main/java/com/nisovin/magicspells/util/Util.java
@@ -576,7 +576,7 @@ public static <C extends Collection<Material>> C getMaterialList(List<String> st
 
 	public static <E extends Enum<E>> E enumValueSafe(Class<E> clazz, String name) {
 		try {
-			return Enum.valueOf(clazz, name);
+			return Enum.valueOf(clazz, name.toUpperCase());
 		} catch (Exception e) {
 			return null;
 		}
diff --git a/core/src/main/java/com/nisovin/magicspells/util/recipes/CustomRecipes.java b/core/src/main/java/com/nisovin/magicspells/util/recipes/CustomRecipes.java
index 7b678fad8..43358d08c 100644
--- a/core/src/main/java/com/nisovin/magicspells/util/recipes/CustomRecipes.java
+++ b/core/src/main/java/com/nisovin/magicspells/util/recipes/CustomRecipes.java
@@ -26,7 +26,7 @@ public static void load(ConfigurationSection recipesSection) {
 			}
 
 			String typeName = config.getString("type", "none");
-			RecipeType type = Util.enumValueSafe(RecipeType.class, typeName.toUpperCase());
+			RecipeType type = Util.enumValueSafe(RecipeType.class, typeName);
 			if (type == null) {
 				MagicSpells.error("Recipe '%s' has an invalid 'type' defined: %s".formatted(recipeKey, typeName));
 				continue;
diff --git a/core/src/main/java/com/nisovin/magicspells/util/recipes/types/RecipeFactory.java b/core/src/main/java/com/nisovin/magicspells/util/recipes/types/RecipeFactory.java
index 273b81513..06e0af95a 100644
--- a/core/src/main/java/com/nisovin/magicspells/util/recipes/types/RecipeFactory.java
+++ b/core/src/main/java/com/nisovin/magicspells/util/recipes/types/RecipeFactory.java
@@ -158,7 +158,7 @@ protected final <E extends Enum<E>> E resolveEnum(ConfigurationSection config, S
 		String received = config.getString(path);
 		if (received == null) return null;
 
-		E value = Util.enumValueSafe(enumClass, received.toUpperCase());
+		E value = Util.enumValueSafe(enumClass, received);
 		if (value != null) return value;
 
 		MagicSpells.error("Invalid %s '%s' for option '%s' on custom recipe '%s'.".formatted(enumClass.getSimpleName(), received, path, config.getName()));