diff --git a/tasks/designate_install.yml b/tasks/designate_install.yml
index ccbf6c0..ff4440d 100644
--- a/tasks/designate_install.yml
+++ b/tasks/designate_install.yml
@@ -93,7 +93,7 @@
 
 - name: Update virtualenv path
   command: >
-    virtualenv-tools --update-path=auto {{ designate_bin | dirname }}
+    virtualenv-tools --update-path=auto --reinitialize {{ designate_bin | dirname }}
   when:
     - not designate_developer_mode | bool
     - designate_get_venv | changed or designate_venv_dir | changed