diff --git a/setup.py b/setup.py
index 972ca0d..57eaec9 100755
--- a/setup.py
+++ b/setup.py
@@ -26,6 +26,6 @@
     entry_points={
         "console_scripts": ["submit50=submit50.__main__:main"]
     },
-    version="3.2.0",
+    version="3.2.1",
     include_package_data=True
 )
diff --git a/submit50/__main__.py b/submit50/__main__.py
index 51e1a6a..0a3a72e 100755
--- a/submit50/__main__.py
+++ b/submit50/__main__.py
@@ -60,21 +60,35 @@ def check_announcements():
         raise Error(res.text.strip())
 
 
-def check_version():
-    """Check that submit50 is the latest version according to submit50.io."""
+def check_version(package_name=__package__, timeout=5):
+    """Check that submit50 is the latest version according to submit.cs50.io and PyPI."""
+    if not __version__:
+        return
+
     # Retrieve version info
-    res = requests.get(f"{SUBMIT_URL}/versions/submit50")
+    res = requests.get(f"{SUBMIT_URL}/versions/submit50", timeout=timeout)
     if res.status_code != 200:
-        raise Error(_("You have an unknown version of submit50. "
+        raise Error(_("Could not connect to submit.cs50.io."
                       "Please visit our status page https://cs50.statuspage.io for more information."))
 
-    # Check that latest version == version installed
-    required_version = version.parse(res.text.strip())
-    local_version = version.parse(__version__)
+    # Get the minimum required version from submit.cs50.io
+    latest_io = version.parse(res.text.strip())
+    current = version.parse(__version__)
+
+    # Get PyPI version
+    latest_pypi = max(
+        requests.get(f"https://pypi.org/pypi/{package_name}/json", timeout=timeout).json()["releases"],
+        key=version.parse
+    )
+    latest_pypi = version.parse(latest_pypi)
+
+    # Check for minimum requirement
+    if current < latest_io:
+        raise Error(_(f"Current version {current} of {package_name} is no longer supported. Run \"pip3 install --upgrade {package_name}\" now to upgrade."))
 
-    if required_version > local_version:
-       raise Error(_("You have an outdated version of submit50. "
-                     "Please upgrade."))
+    # Check for latest version
+    if latest_pypi > current:
+        cprint(f"A newer version of {package_name} is available. Run \"pip3 install --upgrade {package_name}\" now to upgrade.", "magenta")
 
 
 def setup_logging(level):