diff --git a/modules/pip.py b/modules/pip.py
index 34789d1..7ec21df 100644
--- a/modules/pip.py
+++ b/modules/pip.py
@@ -65,6 +65,8 @@ def setup():
             format='\n%(levelname)s: deploy.pip %(message)s',
             level=logging.DEBUG)
 
+    pip_update_latest = "pip install --upgrade pip"
+
     pipinstall_cmd = "pip install -r {requirements}".format(
         requirements=configuration.virtualenv.requirements.filepath)
 
@@ -73,6 +75,7 @@ def setup():
                       pipinstall_cmd)
     else:
         with virtualenv():
+            run(pip_update_latest)
             run(pipinstall_cmd)