diff --git a/cloud-core/src/main/java/cloud/commandframework/CommandTree.java b/cloud-core/src/main/java/cloud/commandframework/CommandTree.java
index bf9d504fb..398ed2712 100644
--- a/cloud-core/src/main/java/cloud/commandframework/CommandTree.java
+++ b/cloud-core/src/main/java/cloud/commandframework/CommandTree.java
@@ -339,7 +339,8 @@ private CommandTree(final @NonNull CommandManager<C> commandManager) {
                 ));
             }
             if (child.getValue() != null) {
-                if (commandQueue.isEmpty()) {
+                // Flag arguments need to be skipped over, so that further defaults are handled
+                if (commandQueue.isEmpty() && !(child.getValue() instanceof FlagArgument)) {
                     if (child.getValue().hasDefaultValue()) {
                         commandQueue.add(child.getValue().getDefaultValue());
                     } else if (!child.getValue().isRequired()) {