diff --git a/readthedocs/doc_builder/python_environments.py b/readthedocs/doc_builder/python_environments.py
index bfd4916206d..b686fc41766 100644
--- a/readthedocs/doc_builder/python_environments.py
+++ b/readthedocs/doc_builder/python_environments.py
@@ -152,7 +152,7 @@ def install_core_requirements(self):
             self.venv_bin(filename='pip'),
             'install',
             '--use-wheel',
-            '-U',
+            '--upgrade',
             '--cache-dir',
             self.project.pip_cache_path,
         ]
@@ -182,14 +182,21 @@ def install_user_requirements(self):
                         break
 
         if requirements_file_path:
-            self.build_env.run(
+            args = [
                 'python',
                 self.venv_bin(filename='pip'),
                 'install',
+            ]
+            if self.project.has_feature(Feature.PIP_ALWAYS_UPGRADE):
+                args += ['--upgrade']
+            args += [
                 '--exists-action=w',
                 '--cache-dir',
                 self.project.pip_cache_path,
                 '-r{0}'.format(requirements_file_path),
+            ]
+            self.build_env.run(
+                *args,
                 cwd=self.checkout_path,
                 bin_path=self.venv_bin()
             )
diff --git a/readthedocs/projects/models.py b/readthedocs/projects/models.py
index 068c3622675..cac8e1248a7 100644
--- a/readthedocs/projects/models.py
+++ b/readthedocs/projects/models.py
@@ -1003,10 +1003,12 @@ def add_features(sender, **kwargs):
     # may be added by other packages
     USE_SPHINX_LATEST = 'use_sphinx_latest'
     USE_SETUPTOOLS_LATEST = 'use_setuptools_latest'
+    PIP_ALWAYS_UPGRADE = 'pip_always_upgrade'
 
     FEATURES = (
         (USE_SPHINX_LATEST, _('Use latest version of Sphinx')),
         (USE_SETUPTOOLS_LATEST, _('Use latest version of setuptools')),
+        (PIP_ALWAYS_UPGRADE, _('Always run pip install --upgrade')),
     )
 
     projects = models.ManyToManyField(