Hi,

Thanks to everyone for their explanation of what is going on. I really appreciate it. To summarize:

Q: I was wondering why I needed to use a self signed cert on by iBoss web filter instead of my wildcard cert?

I had several answers, but I like the one from Robert Lanning the best:

1) Transparent
2) SOCKS
3) Web proxy, where HTTPS is handled by a CONNECT request

1 and 3 are the most common now days.

The certificate check in all cases are the final destination certificate. There is no "Proxy Certificate".

In transparent mode, the TCP SYN is intercepted and the proxy sends its own. It retrieves the certificate from the server and generates its own version. It then fakes being the server back to the client, using its version of the certificate. It just swaps the public key with its own and resigns the certificate with its own CA's private key. It then retrieves the request from the client and duplicates it to the server (if policy allows) and is then able to scan the content coming from the server.

With SOCKS you are basically intercepting the socket() call instead of intercepting the packets, but at the high level you are doing the same as the transparent proxy.

Web proxies are just implemented even higher in the stack. Instead of intercepting the socket() call, the application talks directly with the proxy. In the case of SSL traffic, it asks the proxy to make a blind connection (CONNECT proxy request) and pass the data unhindered. Of course the proxy can interfere with the connection and swap out the certificate and lie about the connection.

In all cases the client must have the CA certificate of the proxy.

cheers,

ski

--
"When we try to pick out anything by itself, we find it
  connected to the entire universe"            John Muir

Chris "Ski" Kacoroski, [email protected], 206-501-9803
or ski98033 on most IM services
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