diff --git a/configure b/configure
index 6ef2da2e631e6e..ea2cfda8f29da5 100755
--- a/configure
+++ b/configure
@@ -32,4 +32,11 @@ else:
       python_cmd_path = which(python_cmd)
       if python_cmd_path and 'pyenv/shims' not in python_cmd_path:
         sys.stderr.write('\t{} {}\n'.format(python_cmd_path, ' '.join(sys.argv[:1])))
+  if sys.version_info > (3, 10):
+    sys.stderr.write('Running "configure" with newer versions of Python has not been ' +
+          'tested and may not work.\n' +
+          'To bypass this check, run "python ./configure.py" and report whether it ' +
+          'works via an issue at https://github.com/nodejs/node\n')
+  else:
+    sys.stderr.write('"configure" will not work with a pre-3.6 version of Python.\n')
   sys.exit(1)