diff --git a/src/main/java/com/extendedclip/deluxemenus/config/DeluxeMenusConfig.java b/src/main/java/com/extendedclip/deluxemenus/config/DeluxeMenusConfig.java
index 586d13c..14a5372 100644
--- a/src/main/java/com/extendedclip/deluxemenus/config/DeluxeMenusConfig.java
+++ b/src/main/java/com/extendedclip/deluxemenus/config/DeluxeMenusConfig.java
@@ -28,6 +28,7 @@
 import java.util.regex.Pattern;
 import java.util.stream.Collectors;
 
+import com.google.common.base.Enums;
 import org.bukkit.DyeColor;
 import org.bukkit.Location;
 import org.bukkit.Material;
@@ -133,6 +134,18 @@ public DeluxeMenusConfig(DeluxeMenus plugin) {
         }
     }
 
+    private List<String> getStringListFromConfig(FileConfiguration config, String path) {
+        if (!config.contains(path)) {
+            return Collections.emptyList();
+        }
+
+        if (config.isList(path)) {
+            return config.getStringList(path);
+        } else {
+            return Collections.singletonList(config.getString(path, ""));
+        }
+    }
+
     public static boolean containsPlaceholders(String text) {
         return PLACEHOLDER_PATTERN.matcher(text).find();
     }
@@ -763,23 +776,25 @@ private Map<Integer, TreeMap<Integer, MenuItem>> loadMenuItems(FileConfiguration
 
             // item flags
             if (c.contains(currentPath + "item_flags")) {
-                if (c.isString(currentPath + "item_flags")) {
-                    String flagAsString = c.getString(currentPath + "item_flags");
-                    ItemFlag flag;
-                    try {
-                        flag = ItemFlag.valueOf(flagAsString.toUpperCase());
-                        builder.itemFlags(Collections.singletonList(flag));
-                    } catch (IllegalArgumentException | NullPointerException ignored) {
+                List<ItemFlag> itemFlags = new ArrayList<>();
+
+                for (String flagAsString : getStringListFromConfig(c, currentPath + "item_flags")) {
+                    ItemFlag flag = Enums.getIfPresent(ItemFlag.class, flagAsString.toUpperCase()).orNull();
+
+                    if (flag == null) {
                         DeluxeMenus.debug(
-                                DebugLevel.HIGHEST,
-                                Level.WARNING,
-                                "Item flag: " + flagAsString + " for item: " + key + " in menu: " + name
-                                        + " is not a valid item flag!"
+                            DebugLevel.HIGHEST,
+                            Level.WARNING,
+                            "Item flag: " + flagAsString + " for item: " + key + " in menu: " + name
+                                + " is not a valid item flag!"
                         );
+                        continue;
                     }
-                } else {
-                    List<ItemFlag> flags = new ArrayList<>();
+
+                    itemFlags.add(flag);
                 }
+
+                builder.itemFlags(itemFlags);
             }
 
             if (c.contains(currentPath + "data")) {