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From what understand, SSL-Strip sits between the target user and the server, establishing a HTTPS connection between itself and the server, and an unsecured, plain old HTTP channel between itself and the target user.

What confuses me is, in a video demo of the tool, one of the prerequisites was an SSL certificate.

Why is the certificate required? Can't the "computer proxy acting as a fake user" send the plaintext back to the user without one? In fact, it seems the only reason a signed SSL certificate would be required would be if the middle-man sent back HTTPS encrypted data back to the user.

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SSLStrip can work of one of two ways:

It will transparently hijack HTTP traffic on a network, watch for HTTPS links and redirects, then map those links into either look-alike HTTP links or homograph-similar HTTPS links.

The video is talking about the latter. So you can still use HTTPS, but try to fool the victim into going to https://www.gmail.attacker.com. Where the attacker owns a valid SSL cert for *.attacker.com. A valid SSL cert isn't required if you're simply replacing https links with http links. i.e. https://www.gmail.com with http://www.gmail.com

http://www.thoughtcrime.org/software/sslstrip/

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