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Transparent Squid issue with Appstore in MacOS Sierra

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Hello,


Here is some information about my squid version,

Squid Cache: Version 3.5.23
Service Name: squid
configure options:  '--prefix=/usr' '--localstatedir=/var/squid' '--libexecdir=/lib/squid' '--srcdir=.' '--datadir=/share/squid' '--sysconfdir=/etc/squid' '--with-default-user=proxy' '--with-logdir=/var/log/squid' '--with-pidfile=/var/run/squid.pid' '--with-openssl' '--enable-ssl-crtd' '--enable-inline' '--disable-arch-native' '--enable-async-io=8' '--enable-storeio=ufs,aufs,diskd,rock' '--enable-removal-policies=lru,heap' '--enable-delay-pools' '--enable-follow-x-forwarded-for' '--enable-url-rewrite-helpers=fake' '--enable-ecap'


We are running squid as transparent proxy and have certs installed in all systems. Until recently all our systems were ubuntu or windows. Recently we added mac os Seirra and the biggest issue we had with mac is even after installing certificates. Few apps have problems.

Our biggest problem is Itunes Store. It just doesn't work for some reason. if we check the log we get random ip's trying to connect via 443 port but it doesn't connect.
Also Skype for Mac does not work. strangely this works for windows and ubuntu in our network. Again we see the same behavior.

both of these apps does not work even in Iphone and Ipad.

I believe someone must be able to configure transparent squid with Mac. can anyone tell me if i need to do anything extra for Mac setup.
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