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Network Security CISSP-Discussion
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Re: [CISSP-D] Proxy Servers and SSL

Subject: Re: [CISSP-D] Proxy Servers and SSL
Date: Wed, 27 Oct 2004 13:21:23 +1300


PLDT FOA-Armando Bonifacio wrote:

I recently went through a phone interview for a company and they asked 
me a question regarding deafeating proxy servers.
 
Of course my initial answers were using public proxy servers that mask 
the actual URL if the proxy servers use URL based filtering, or type 
in the IP address of the website instead of the domain. There are a 
lot of public proxy servers that do URL masking anyway, such as 
usproxy.net.
 
Then came the idea of SSL.
 
Let's say the proxy server has a filter turned on for domain.com
 
If the user, uses https://domain.com, won't the proxy server still be 
able to block this?
 
My interviewer said that it won't. But i was the under the impression 
that it should.
 
The assumption is that the proxy server can proxy both 80 and 443 
requests.
 
Looking forward to an enlightenment from the group.
 
Anton

Anton,

HTTP proxies are generally HTTPS 'aware', but they don't can't filter 
past a point, due to the contents of the transmission being encrypted.

When the inital connection to the proxy arrives, the client issues the 
command "CONNECT <host>:<port>" The proxy then opens a socket to the 
remote site, and from then on the client talks over SSL to the end 
server, the proxy is just redirecting a bitstream that it can't read.

The proxy can obviously use the connect request to perform an 
accept/deny decision, but that's as smart as it gets.

Hope this helps,

Glenn Phillips, CISSP.






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