Hello Mathias, I would like to use you OpenVPN GUI for Windows to authenticate over an NTLM proxy in Windows and wonder if you're thinking about asking and supplying the password for NTLM-proxy authentication or planing on doing so.
The very recent versions of (2.2.x) of OpenVPN support not only basic authentcation but in addition NTLM authentication which is necessary to connect via an ISA proxy, when creating a config file for Windows GUI it was possible to specify the proxy password but it tried to authentication using basic authentication which was disabled in the ISA proxy for security reasons. Example config: client dev tun proto tcp nobind remote edge1.glanzmann.de 443 resolv-retry infinite persist-key persist-tun ca edge1ca.crt ns-cert-type server comp-lzo verb 3 mute 20 auth-user-pass tun-mtu 1400 http-proxy 192.168.1.211 8080 credentials.txt ntlm In the last line you see the changes. There is an ntlm at the end and a file (I think you already have that with username and password in it). >From the OpenVPN Man page: -http-proxy server port [authfile|'auto'|'auto-nct'] [auth-method] Connect to remote host through an HTTP proxy at address server and port port. If HTTP Proxy-Authenticate is required, authfile is a file containing a username and password on 2 lines, or "stdin" to prompt from console. auth-method should be one of "none", "basic", or "ntlm". HTTP Digest authentication is supported as well, but only via the auto or auto-nct flags (below). The auto flag causes OpenVPN to automatically determine the auth-method and query stdin or the management interface for username/password credentials, if required. This flag exists on OpenVPN 2.1 or higher. The auto-nct flag (no clear-text auth) instructs OpenVPN to automatically determine the authentication method, but to reject weak authentication protocols such as HTTP Basic Authentication. Source: http://www.openvpn.net/index.php/open-source/documentation/manuals/427-openvpn-22.html Maybe you could add a checkbox which lets a user choose between none, basic, ntlm, auto, or auto-nct authentication. Cheers, Thomas