Thanks for your input. After further testing (which I thought I already tested and determined was not the case...), it looks like it fails any time a certificate is "broken" when using a proxy server even with ssl bumping turned off. If I use a host file to make the cert name not match, I get the same error. Browse to a site with a set signed cert, same error. So this seems to be a little more generic of an issue than I suspected. I appreciate your feedback. We'll re-engage Apple with the new details and see how it goes.
On Thu, Oct 30, 2014 at 9:12 PM, Amos Jeffries <squid3@xxxxxxxxxxxxx> wrote:
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Hash: SHA1
On 31/10/2014 8:30 a.m., inetjunkmail wrote:
> We have an explicit squid proxy running ssl bump that works fine
> for iOS 7 but Safari on iOS 8 gives an error stating that "There
> was a problem communicating with the secure web proxy server
> (HTTPS)." when browsing to an SSL site that is bumped.
>
> We can wipe an iOS 7 device, add the proxy CA to the trust store,
> and successfully browse to an intercepted site. Doing the same
> process with iOS 8 reveals the error.
>
> The error has been reproduced on two other intercepting proxy
> solutions.
>
> Accessing SSL sites directly or non-intercepted is fine even if
> the certificate is self signed or untrusted in any way.
>
> We've tried contacting Apple and they are pressing hard to close
> the case saying that they don't support interception; contact the
> vendor. The fact that it works fine with iOS 7, and the same error
> is reproducible with 3 separate SSL interception proxies suggests
> to me it's on them.
Perhapse it is a result of the arms-race happening in the SSL/TLS
area. Try upgrading to the latest Squid-3.5 and see if the bumping
features there help. We know for certain that the ssl-bump features in
3.2 and 3.3 are useless with a growing number of websites using HSTS
and "cert-pinning".
But I dont think it is that clearly "on them". Interception *is* an
attack on your users, and illegal in a lot of cases as well. It is
reasonable for them not to support it.
>
> Is anyone else running into this? Is anyone else working?
You are the first person noticably involved with MacOS / iOS in any
way to post anything here in a long while. So unless you get a direct
the answer assume it is "none of us use iOS like this".
Amos
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