diff --git a/flask/cli.py b/flask/cli.py
index efc1733e..f7c603a1 100644
--- a/flask/cli.py
+++ b/flask/cli.py
@@ -670,7 +670,7 @@ class CertParamType(click.ParamType):
 
             obj = import_string(value, silent=True)
 
-            if sys.version_info < (2, 7):
+            if sys.version_info < (2, 7, 9):
                 if obj:
                     return obj
             else:
@@ -687,7 +687,7 @@ def _validate_key(ctx, param, value):
     cert = ctx.params.get('cert')
     is_adhoc = cert == 'adhoc'
 
-    if sys.version_info < (2, 7):
+    if sys.version_info < (2, 7, 9):
         is_context = cert and not isinstance(cert, (text_type, bytes))
     else:
         is_context = isinstance(cert, ssl.SSLContext)
diff --git a/tests/test_cli.py b/tests/test_cli.py
index 387eeeba..ee038265 100644
--- a/tests/test_cli.py
+++ b/tests/test_cli.py
@@ -521,12 +521,12 @@ def test_run_cert_import(monkeypatch):
         run_command.make_context('run', ['--cert', 'not_here'])
 
     # not an SSLContext
-    if sys.version_info >= (2, 7):
+    if sys.version_info >= (2, 7, 9):
         with pytest.raises(click.BadParameter):
             run_command.make_context('run', ['--cert', 'flask'])
 
     # SSLContext
-    if sys.version_info < (2, 7):
+    if sys.version_info < (2, 7, 9):
         ssl_context = object()
     else:
         ssl_context = ssl.SSLContext(ssl.PROTOCOL_SSLv23)