[squid-users] Safari 9 vs. SSL Bump

Alex Rousskov rousskov at measurement-factory.com
Wed Oct 14 14:34:14 UTC 2015

On 10/13/2015 09:08 PM, Dan Charlesworth wrote:

> But in reality ssl_bump peek step1 & ssl_bump bump step3 is actually
> splicing everything, it seems.

This may not be related to your specific problem, but I want to clarify
the above.

  ssl_bump peek step1
  ssl_bump bump step3

A recent Squid mis-configured using the above sketch should indeed
splice everything. When Squid reaches bumping step2, no ssl_bump rule
matches, so Squid uses the previous step rule to decide what to do.
Since peeking implies splicing, Squid splices at step2 and never gets to

It is possible that, in his "bump at step3" recommendation below, Amos
was talking about this kind of configuration:

  ssl_bump stare all
  ssl_bump bump all

Bugs notwithstanding, the above results in bumping at step3.


>> On 14 Oct 2015, at 1:51 PM, Amos Jeffries <squid3 at treenet.co.nz> wrote:
>> On 14/10/2015 1:13 p.m., Dan Charlesworth wrote:
>>> Throwing this out to the list in case anyone else might be trying to get SSL Bump to work with the latest version of Safari.
>>> Every other browser on OS X (and iOS) is happy with bumping for pretty much all HTTPS sites, so long as the proxy’s CA is trusted. 
>>> However Safari throws generic “secure connection couldn’t be established” errors for many popular HTTPS sites in including:
>>> - wikipedia.org
>>> - mail.google.com
>>> - twitter.com
>>> - github.com
>>> But quite a number of others work, such as youtube.com.
>>> This error gets logged to the system whenever it occurs:
>>> com.apple.WebKit.Networking: NSURLSession/NSURLConnection HTTP load failed (kCFStreamErrorDomainSSL, -9802)
>>> Apparently this is related to Apple’s new “App Transport Security” protections, in particular, the fact that “the server doesn’t support forward secrecy”. Even though it doesn’t seem to be affecting mobile Safari on iOS 9 at all.
>>> It’s also notable that Safari seems perfectly happy with legacy server-first SSL bumping. 
>>> I’m using Squid 3.5.10 and this is my current config: https://gist.github.com/djch/9b883580c6ee84f31cd1
>>> Anyone have any idea what I can try?
>> You can try bump at step3 (roughly equivalent to server-first) instead
>> of step2 (aka client-first).
>> Amos
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