diff --git a/rattail_fabric/python.py b/rattail_fabric/python.py
index 3192d0f..aeeb43a 100644
--- a/rattail_fabric/python.py
+++ b/rattail_fabric/python.py
@@ -50,21 +50,26 @@ def install_pip(use_apt=False):
             apt.install('python-pkg-resources', 'python-setuptools')
             sudo('easy_install pip')
             sudo('apt-get --assume-yes purge python-setuptools')
-        pip('setuptools')
-        pip('pip', 'wheel', 'ndg-httpsclient')
+            pip('setuptools')
+        pip('pip', upgrade=True)
+        pip('setuptools', 'wheel', 'ndg-httpsclient', upgrade=True, upgrade_strategiy='eager')
 
 
 def pip(*packages, **kwargs):
     """
     Install one or more packages via ``pip install``.
     """
+    upgrade = kwargs.pop('upgrade', False)
+    upgrade = '--upgrade' if upgrade else ''
     upgrade_strategy = kwargs.pop('upgrade_strategy', None)
-    if upgrade_strategy:
+    if upgrade and upgrade_strategy:
         upgrade_strategy = '--upgrade-strategy {}'.format(upgrade_strategy)
+    else:
+        upgrade_strategy = ''
     if kwargs:
         abort("Unknown kwargs for pip(): {}".format(kwargs))
     packages = ["'{}'".format(p) for p in packages]
-    sudo('pip install --upgrade {} {}'.format(upgrade_strategy or '', ' '.join(packages)))
+    sudo('pip install {} {} {}'.format(upgrade, upgrade_strategy, ' '.join(packages)))
 
 
 def install_virtualenvwrapper(workon_home=None, user='root', use_apt=False):
@@ -77,7 +82,7 @@ def install_virtualenvwrapper(workon_home=None, user='root', use_apt=False):
     if use_apt:
         apt.install('virtualenvwrapper')
     else:
-        pip('virtualenvwrapper')
+        pip('virtualenvwrapper', upgrade=True)
         configure_virtualenvwrapper('root', workon_home)
         if user != 'root':
             configure_virtualenvwrapper(user, workon_home)
@@ -117,10 +122,10 @@ def mkvirtualenv(name, python=None, user=None, workon_home=None,
         else:
             pip_req = 'pip'
         with workon(name):
-            pip('six')
-            pip(pip_req)
+            pip('six', upgrade=True)
+            pip(pip_req, upgrade=True)
             if upgrade_setuptools:
-                pip('setuptools', 'wheel', 'ndg-httpsclient', upgrade_strategy=upgrade_strategy)
+                pip('setuptools', 'wheel', 'ndg-httpsclient', upgrade=True, upgrade_strategy=upgrade_strategy)
     if user:
         with cdvirtualenv(name, workon_home=workon_home):
             mkdir('app/log', owner='{0}:{0}'.format(user))