[squid-users] MITM the MITM

Grant Taylor gtaylor at tnetconsulting.net
Tue Jan 4 04:19:13 UTC 2022


On 1/3/22 5:19 PM, Will BMD wrote:
> Hey all,

Hi,

> From the Firewalls perspective all client connections are originating 
> as the proxy server. We're wanting to use the https inspect feature of 
> the firewall,

I'm taking "HTTPS inspect" to be the firewall's counterpart to ssl_bump.

> but according to our firewall documentation it appears due to the 
> location of our proxy servers we would be unable to do so.

Where does the firewall documentation / vendor want the proxy server to be?

> My question is, if the proxy is behaving as a MITM between itself and 
> the client, can't the Firewall do the same thing between itself and the 
> proxy?

I don't see why it can't.

> I suspect it is possible, but might potentially involve a lot of 
> headaches and a big hit on performance?

Do you are about original client IP addresses?  If not, then I think 
this should be as simple as one proxy (Squid) talking to another proxy 
(firewall).

> Any insight into this would be greatly appreciated.

I would wonder if WCCP /might/ be a viable option in this scenario or 
not.  As in configure clients to use the firewall as a proxy and have 
the firewall do it's thing while leveraging Squid's caching capability 
via WCCP.

There might also be the some room for having Squid view the firewall as 
a parent proxy.



-- 
Grant. . . .
unix || die

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