This is being tracked in https://bugzilla.sudo.ws/show_bug.cgi?id=988 The problem was introduced during a refactor in sudo 1.9.7. The fix is a single line change of TLS_client_method() to TLS_method(). OpenSSL cares about TLS_client_method() vs. TLS_server_method() where LibreSSL does not. I'm verifying the fix now. - todd