To filter HTTPS traffic in this way, you *do* in fact need to "pose as
Google" using a self-signed cert. You're essentially performing a MitM
attack against your own users, in that scenario - and yes, think of the
damage you could do. If you don't want to do that, then you can't filter
the HTTPS traffic.

On Thu, Oct 9, 2014 at 7:46 PM, Ski Kacoroski <[email protected]> wrote:

> Hi,
>
> I need someone with more certiticate-fu than I have.  I have an iBoss web
> filtering device that sits in between our internal users and the internet.
> We are trying to set it up to also filter https web pages which means it
> has to decrypt the connection to see what is going on. They are claiming
> that we have to use a self-signed cert on their device instead of our
> wildcard *.nsd.org cert and then install the public key on all the
> browsers of our internal machines which, as you can imagine, is not
> something we want to do or maintain.  I have 6500+ macs, 3000 chromebooks,
> 2000 ipads, 1000 windows, and several hundred other things such as kindles,
> etc.  In addition, several of these have multiple browsers.
>
> I appreciate any comments or ideas why we cannot get our wildcard cert to
> work (it works with erverything else except for an old Oracle application
> server where I had to get a machine specific cert).
>
> Their description is:
> --------------------------------
>
> * The certificate needed to do the decryption must be trusted by the
> browser to sign ALL domains.
> * GoDaddy and other Certificate Authorities (CA) will not sign a
> certificate for use with domains other than your own. So… The certificate
> must be self-signed with no verification path back to a trusted CA.
> * The *.nsd.org certificate you have will work to access the iboss UI,
> block or login pages.
>
> Follow up email states:
> The first 2 bullet points from yesterday are important to understand.
> There is no possibility of getting a CA certificate from anyone that is
> trusted by the browsers. As far as we have seen it takes a CA cert to be
> fully functional for intercepting HTTPS traffic and re-sign so that the
> browser will accept it. This means using a self-signed cert. To stress the
> point, imagine what damage you could do with a certificate that allowed you
> to pose as Google without the browser alerting the user.
>
> I can’t answer why we have had the limited success with decrypting using
> the *.nsd.org or how far we can push it. In a couple cases we were able
> to get everything working unless Chrome was used. In another case IE seemed
> to be the biggest problem. They each perform validity checks of their own
> design. Technically, the cert you have should not be accepted to sign
> anything. That is not a feature of the cert (CA:FALSE).
> --------------------------------
>
> 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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