diff --git a/awx/__init__.py b/awx/__init__.py
index 2c4a64f58e..08837cdfd5 100644
--- a/awx/__init__.py
+++ b/awx/__init__.py
@@ -41,9 +41,14 @@ def prepare_env():
     local_site_packages = os.path.join(os.path.dirname(__file__), 'lib',
                                        'site-packages')
     site.addsitedir(local_site_packages)
-    # Work around https://bugs.python.org/issue7744
-    # by moving  local_site_packages to the front of sys.path
-    sys.path.insert(0, sys.path.pop())
+    try:
+        index = sys.path.index(local_site_packages)
+        sys.path.pop(index)
+        # Work around https://bugs.python.org/issue7744
+        # by moving  local_site_packages to the front of sys.path
+        sys.path.insert(0, local_site_packages)
+    except ValueError:
+        pass
     # Hide DeprecationWarnings when running in production.  Need to first load
     # settings to apply our filter after Django's own warnings filter.
     from django.conf import settings