diff --git a/check50.py b/check50.py
index 19397fca..0ba79cd0 100755
--- a/check50.py
+++ b/check50.py
@@ -14,6 +14,7 @@
 import requests
 import shutil
 import signal
+import site
 import subprocess
 import sys
 import tempfile
@@ -41,6 +42,12 @@
 except ImportError:
     from pipes import quote
 
+
+try:
+    from importlib import reload
+except (ImportError, AttributeError):
+    from imp import reload
+
 import config
 
 __all__ = ["App", "check", "Checks", "Child", "EOF", "Error", "File", "Mismatch", "valgrind"]
@@ -300,7 +307,7 @@ def import_checks(identifier):
     for dir in [checks_root, os.path.dirname(config.check_dir)]:
         requirements = os.path.join(dir, "requirements.txt")
         if os.path.exists(requirements):
-            args = ["install", "-r", requirements]
+            args = ["install", "--upgrade", "-r", requirements]
             # If we are not in a virtualenv, we need --user
             if not hasattr(sys, "real_prefix"):
                 args.append("--user")
@@ -314,6 +321,10 @@ def import_checks(identifier):
                 raise InternalError("failed to install dependencies in ({})".format(
                     requirements[len(config.args.checkdir) + 1:]))
 
+            # Refresh sys.path to look for newly installed dependencies
+            reload(site)
+
+
     try:
         # Import module from file path directly.
         module = imp.load_source(slug, os.path.join(config.check_dir, "__init__.py"))
diff --git a/setup.py b/setup.py
index 41ee9be9..92fd27a9 100644
--- a/setup.py
+++ b/setup.py
@@ -59,5 +59,5 @@ class CustomInstall(install):
         "console_scripts": ["check50=check50:main"]
     },
     url="https://github.com/cs50/check50",
-    version="2.2.6"
+    version="2.2.7"
 )