diff --git a/hack/generate-cli-docs.sh b/hack/generate-cli-docs.sh
index d9da8b25b7..a9504fc1bc 100755
--- a/hack/generate-cli-docs.sh
+++ b/hack/generate-cli-docs.sh
@@ -1,6 +1,9 @@
 # Copyright 2024 Daytona Platforms Inc.
 # SPDX-License-Identifier: Apache-2.0
 
+# Clean up existing documentation files
+rm -rf docs hack/docs
+
 # Generate default CLI documentation files in folder "docs"
 go run cmd/daytona/main.go generate-docs