diff --git a/modules/deploy.py b/modules/deploy.py
index ec1515c..609c45b 100644
--- a/modules/deploy.py
+++ b/modules/deploy.py
@@ -9,6 +9,7 @@ from utils import print_console
 
 from pip import setup_virtualenv
 from pip import setup as pip_requirements
+from pip import upgrade as pip_upgrade
 
 import os
 
@@ -79,6 +80,7 @@ def bootstrap():
 
     setup_virtualenv()
 
+    pip_upgrade()  # upgrade pip to latest version in the virtualenv
     pip_requirements()
 
     #
diff --git a/modules/pip.py b/modules/pip.py
index 7ec21df..e4b8f69 100644
--- a/modules/pip.py
+++ b/modules/pip.py
@@ -53,6 +53,29 @@ def setup_virtualenv():
             run(mkvirtualenv_cmd)
 
 
+@task
+def upgrade():
+    """
+    upgrade pip to latest version
+    """
+
+    # configuration = env.config
+
+    if env.debug:
+        logging.basicConfig(
+            format='\n%(levelname)s: deploy.pip %(message)s',
+            level=logging.DEBUG)
+
+    pipinstall_cmd = "pip install --upgrade pip"
+
+    if env.debug:
+        logging.debug("with virtualenv(): run(\"\n\t%s\n\t\")" %
+                      pipinstall_cmd)
+    else:
+        with virtualenv():
+            run(pipinstall_cmd)
+
+
 @task
 def setup():
     """
@@ -65,8 +88,6 @@ 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)
 
@@ -75,7 +96,6 @@ def setup():
                       pipinstall_cmd)
     else:
         with virtualenv():
-            run(pip_update_latest)
             run(pipinstall_cmd)