diff --git a/Tools/scripts/checkpip.py b/Tools/scripts/checkpip.py
new file mode 100644
index 0000000..1b6049d
--- /dev/null
+++ b/Tools/scripts/checkpip.py
@@ -0,0 +1,31 @@
+#!/usr/bin/env python2
+"""
+Checks that the version of the projects bundled in ensurepip are the latest
+versions available.
+"""
+import ensurepip
+import json
+import urllib2
+import sys
+
+
+def main():
+    outofdate = False
+
+    for project, version in ensurepip._PROJECTS:
+        data = json.loads(urllib2.urlopen(
+            "https://pypi.python.org/pypi/{}/json".format(project),
+        ).read().decode("utf8"))
+        upstream_version = data["info"]["version"]
+
+        if version != upstream_version:
+            outofdate = True
+            print("The latest version of {} on PyPI is {}, but ensurepip "
+                  "has {}".format(project, upstream_version, version))
+
+    if outofdate:
+        sys.exit(1)
+
+
+if __name__ == "__main__":
+    main()