diff --git a/python-env/defaults/main.yml b/python-env/defaults/main.yml
index 42388e5d..590f3c10 100644
--- a/python-env/defaults/main.yml
+++ b/python-env/defaults/main.yml
@@ -2,5 +2,14 @@
 py_env_install: False
 py_env_pkgs_state: installed
 py_env_site: False
+py_env_trusty_workaround: True
+py_env_get_pip_url: https://bootstrap.pypa.io/get-pip.py
+
 py_env_basic_pkgs:
   - python-pip
+
+py_env_pip_fix_ssl_warnings:
+  - pyOpenSSL
+  - cryptography
+  - idna
+  - certifi
diff --git a/python-env/files/pip-fixer.sh b/python-env/files/pip-fixer.sh
new file mode 100644
index 00000000..c4ecda36
--- /dev/null
+++ b/python-env/files/pip-fixer.sh
@@ -0,0 +1,7 @@
+#!/bin/bash
+
+GET_PIP=/usr/local/lib/get-pip.py
+
+chmod 755 $GET_PIP
+
+$GET_PIP
diff --git a/python-env/tasks/main.yml b/python-env/tasks/main.yml
index 62b57791..5cf63996 100644
--- a/python-env/tasks/main.yml
+++ b/python-env/tasks/main.yml
@@ -1,6 +1,5 @@
 ---
 - block:
-    
     - name: Install python pip
       apt: name={{ item }} state={{ py_env_pkgs_state }} update_cache=yes cache_valid_time=600
       with_items: '{{ py_env_basic_pkgs | default([]) }}'
@@ -13,8 +12,45 @@
       apt: name={{ item }} state={{ py_env_pkgs_state }}  update_cache=yes cache_valid_time=600
       with_items: '{{ py_pip_deps | default([]) }}'
 
+    - name: Fix the ssl warnings installing some ssl libraries
+      pip: name={{ item }}
+      with_items: '{{ py_env_pip_fix_ssl_warnings | default ([]) }}'
+      when:
+        - not py_env_trusty_workaround
+        - is_trusty
+
+    - name: Install a list of pip packages
+      pip: name={{ item }}
+      with_items: '{{ py_env_pip_pkgs | default ([]) }}'
+      when:
+        - not py_env_trusty_workaround
+        - is_trusty
+
+  when: py_env_install
+  tags: [ "python", "py_env" ]
+
+- block:
+    - name: Install the get-pip.py pip downloader
+      get_url: url={{ py_env_get_pip_url }} dest=/usr/local/lib/get-pip.py
+
+    - name: Install a script that fixes the broken trusty pip package
+      copy: src=pip-fixer.sh dest=/usr/local/bin/python-pip-fixer mode=0755 owner=root group=root
+      register: python_pip_fixer
+
+    - name: Fix the trusty pip installation
+      shell: /usr/local/bin/python-pip-fixer
+      when: ( python_pip_fixer | changed )
+
+    - name: Fix the ssl warnings installing some ssl libraries
+      pip: name={{ item }}
+      with_items: '{{ py_env_pip_fix_ssl_warnings | default ([]) }}'
+
     - name: Install a list of pip packages
       pip: name={{ item }}
       with_items: '{{ py_env_pip_pkgs | default ([]) }}'
 
+  when:
+    - py_env_trusty_workaround
+    - py_env_install
+    - is_trusty
   tags: [ "python", "py_env" ]