diff --git a/tools/deployment-cli-tools/ch_cli_tools/skaffold.py b/tools/deployment-cli-tools/ch_cli_tools/skaffold.py
index 774234b9..c0de5764 100644
--- a/tools/deployment-cli-tools/ch_cli_tools/skaffold.py
+++ b/tools/deployment-cli-tools/ch_cli_tools/skaffold.py
@@ -143,7 +143,8 @@ def process_build_dockerfile(dockerfile_path, root_path, global_context=False, r
             def identify_unicorn_based_main(candidates):
                 import re
                 gunicorn_pattern = re.compile(r"gunicorn")
-                for candidate in candidates:
+                # sort candidates, shortest path first
+                for candidate in sorted(candidates,key=lambda x: len(x.split("/"))):
                     dockerfile_path = f"{candidate}/.."
                     while not exists(f"{dockerfile_path}/Dockerfile") and abspath(dockerfile_path) != abspath(root_path):
                         dockerfile_path += "/.."