diff --git a/roles/bootstrap-os/tasks/bootstrap-ubuntu.yml b/roles/bootstrap-os/tasks/bootstrap-ubuntu.yml
index 91b2ce1fb..64df71bd6 100644
--- a/roles/bootstrap-os/tasks/bootstrap-ubuntu.yml
+++ b/roles/bootstrap-os/tasks/bootstrap-ubuntu.yml
@@ -10,11 +10,12 @@
     - pip
   tags: facts
 
-- name: Bootstrap | Install python 2.x
-  raw: >
+- name: Bootstrap | Install python 2.x and pip
+  raw:
     apt-get update && \
-    DEBIAN_FRONTEND=noninteractive apt-get install -y python-minimal pip
-  when: need_bootstrap | failed
+    DEBIAN_FRONTEND=noninteractive apt-get install -y python-minimal python-pip
+  when:
+    "{{ need_bootstrap.results | map(attribute='rc') | sort | last | bool }}"
 
 - set_fact:
     ansible_python_interpreter: "/usr/bin/python"