Something like this is actually done in big institutions.

Some year ago I did a project in a big bank in Switzerland.
Pretty much everybody there was using the "official" Internet Explorer. The funny thing was that when you used Firefox you got warnings on ssl-secured sites that the certificate did not match the domain-name. In fact it turned out that their proxy just returned a self-signed certificate and the "official" Internet Explorer had been modified so that it would silently accept this certificate.

So in effect they had a man-in-the-middle with hardly anybody noticing it.

So if you want to do it yourself the important thing is that you must be able to control the browser (and I assume that if you can force your users to use IE you're already halfway there).

And as an aside: Never trust the browsers that are rolled out by the IT-departments of big organisations.

In reply to Re^2: HTTP::Proxy SSL Man in the middle by morgon
in thread HTTP::Proxy SSL Man in the middle by locked0wn

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