SimpLite MSN Encryption on Ubuntu Linux

Many years ago I discovered a fantastic utility for encrypting MSN conversations called SIMP. Simp-Lite is fantastic stuff that essentially works as a personal proxy. It’s completely transparent to the end user after initial set up and it passes WAF (Wife Acceptance Factor) tests with flying colours. After my Windows desktop died a death the other week, I decided to rebuild with Ubuntu Linux and try out Dapper Drake. Of course, when I went to try and find a plugin for GAIM I couldn’t find one other than Gaim-Encrypt which, after telling people for years to use SIMP just wasn’t compatible. I can’t exactly use MSN without SIMP, as most of my contacts won’t speak to me, except to rib me about not using crypto.

Enter Wine…

Wine is a Win32 API implementation for Unix and Unix-like Operating Systems. Basically it’s a translation layer (note I didn’t say emulator) that lets users of other Operating Systems (e.g. Ubuntu) run Win32 Applications. I used to use wine many years ago. In 2003 I experienced the pain of configuring Internet Explorer under Wine, and as far back as 2000 I was suffering with the agony of getting proprietary backup client applications to work with it so I was braced for a session.

Amazingly Wine was trivial to install on ubuntu:

apt-get install wine

Now to try installing Simp. After downloading the .MSI file from the Secway web site I found that I couldn’t run the installer and cabextract just provided me with a bunch of useless files. To install Secway you need to use the MSI installer from Microsoft, available here.

Now installing Secway consists of typing the following:

wine msiexec /i SimpLite-MSN-2_2_0-en.msi

Follow the on-screen instructions, and when you get to choose your client type choose ‘unlisted MSN client’. Keep on going through the install process and finish, then sign into Simp.

Now it’s time to configure an MSN client. I’m going to use GAIM but any MSN client should work. Set up your account as normal, but then when adding your account go to Show more options and Change the Proxy type from Use Global Proxy Settings to Socks 4. Set the host to 127.0.0.1 and port to 11863. Now log into MSN and you should find that Simp works (or at least seems to) perfectly. The screenshot below is of me talking with someone who doesn’t have SIMP installed, although I have since been chatting away to people with Simp encryption.

I really can’t stress enough how far Wine has come on in recent years in terms of usability. There was a time where I’d expect it to at most partially work after heaps of tweaking, but it appears that it just works fine. I’m off to see what else I can run. But first some questions:

• What do you use wine for?
• How difficult did you find it?