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Sophos Web Appliance issue - Cannot connect to App Store from Mac

Hi All,

I have a curious issue with a couple of Macs in our office. When I set the proxy in system network proxy to our Sophos Web Appliance I cannot connect to the Apple App Store. I can connect to the iTunes store

I get the following error on the app store.

"App Store cannot verify secure connection with the App Store"

Would you like to connect anyway?

If I select 'continue' the screen will flash black and grey while it fails to connect.

If I check my logs I can see it allowing it through with no blocks, but it still fails.

 https://swcdnlocator.apple.com:4432013/10/25 09:29 PMAllowed
 https://swscan.apple.com:4432013/10/25 09:29 PMAllowed
 https://swdist.apple.com:4432013/10/25 09:28 PMAllowed (19)
 https://swdist.apple.com:4432013/10/25 08:57 PMAllowed (19)
 https://swcdnlocator.apple.com:4432013/10/25 08:57 PMAllowed
 https://swscan.apple.com:4432013/10/25 08:57 PMAllowed
 https://xp.apple.com:4432013/10/25 08:57 PMAllowed (2)
 https://client-api.itunes.apple.com:4432013/10/25 08:56 PMAllowed (20)
 https://itunes.apple.com:4432013/10/25 08:56 PMAllowed (9)
 https://securemetrics.apple.com:4432013/10/25 08:56 PMAllowed (2)
 https://metrics.mzstatic.com:4432013/10/25 08:56 PMAllowed (2)
 https://s.mzstatic.com:4432013/10/25 08:56 PMAllowed (38)
 https://itunes.apple.com:4432013/10/25 08:55 PMAllowed (3)
 https://s.mzstatic.com:4432013/10/25 08:55 PMAllowed (69)
 https://swdist.apple.com:4432013/10/25 08:54 PMAllowed (19)
 https://swcdnlocator.apple.com:4432013/10/25 08:54 PMAllowed
 https://swscan.apple.com:4432013/10/25 08:54 PM

Allowed

I have setup the following to try and allow it through - 

Additional Site List

apple.com

Globally Allowed Site

Trusted

Ive also added in an additional policy with the above allowing the IP address of the Mac's (so authentication is not needed)

And in System > Authentication 
On authentication failure:
Allow access (use IP-based policy rules)

I do not get this issue using a Cisco Ironport.

Any help is appreciated!

Thanks,

Milton

:44497


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