diff --git a/playbooks/roles/pip3/tasks/default.yaml b/playbooks/roles/pip3/tasks/default.yaml
new file mode 100644
index 0000000000..e58d05ae4e
--- /dev/null
+++ b/playbooks/roles/pip3/tasks/default.yaml
@@ -0,0 +1,5 @@
+- name: Download get-pip.py
+  command: wget https://bootstrap.pypa.io/get-pip.py
+  args:
+    chdir: /var/lib
+    creates: /var/lib/get-pip.py
diff --git a/playbooks/roles/pip3/tasks/main.yaml b/playbooks/roles/pip3/tasks/main.yaml
index 2ad311161a..091e3e60fa 100644
--- a/playbooks/roles/pip3/tasks/main.yaml
+++ b/playbooks/roles/pip3/tasks/main.yaml
@@ -16,11 +16,15 @@
     state: present
   when: ansible_distribution_release != 'xenial'
 
-- name: Download get-pip.py
-  command: wget https://bootstrap.pypa.io/get-pip.py
-  args:
-    chdir: /var/lib
-    creates: /var/lib/get-pip.py
+- name: Download OS/Python specific get-pip.py
+  include_tasks: "{{ get_pip_os }}"
+  with_first_found:
+    - "{{ ansible_distribution_release }}.yaml"
+    - "{{ ansible_distribution }}.yaml"
+    - "{{ ansible_os_family }}.yaml"
+    - "default.yaml"
+  loop_control:
+    loop_var: get_pip_os
 
 - name: Install pip
   command: python3 /var/lib/get-pip.py
diff --git a/playbooks/roles/pip3/tasks/xenial.yaml b/playbooks/roles/pip3/tasks/xenial.yaml
new file mode 100644
index 0000000000..734fa5d6d1
--- /dev/null
+++ b/playbooks/roles/pip3/tasks/xenial.yaml
@@ -0,0 +1,6 @@
+# https://github.com/pypa/get-pip/issues/83
+- name: Download get-pip.py
+  command: wget https://bootstrap.pypa.io/3.5/get-pip.py
+  args:
+    chdir: /var/lib
+    creates: /var/lib/get-pip.py