diff --git a/roles/bootstrap-os/tasks/bootstrap-ubuntu.yml b/roles/bootstrap-os/tasks/bootstrap-ubuntu.yml
index 738a45c1a81b994091e5e26590865bc1d60302a1..91b2ce1fb1df58c8be7098668cf1e1cb01fa0e58 100644
--- a/roles/bootstrap-os/tasks/bootstrap-ubuntu.yml
+++ b/roles/bootstrap-os/tasks/bootstrap-ubuntu.yml
@@ -2,13 +2,18 @@
 #  raw: cat /etc/issue.net | grep '{{ bootstrap_versions }}'
 
 - name: Bootstrap | Check if bootstrap is needed
-  raw: which python
+  raw: which "{{ item }}"
   register: need_bootstrap
   failed_when: false
+  with_items:
+    - python
+    - pip
   tags: facts
 
 - name: Bootstrap | Install python 2.x
-  raw: apt-get update && DEBIAN_FRONTEND=noninteractive apt-get install -y python-minimal
+  raw: >
+    apt-get update && \
+    DEBIAN_FRONTEND=noninteractive apt-get install -y python-minimal pip
   when: need_bootstrap | failed
 
 - set_fact: