"Cannot connect to the iTunes Store" when using WiFi and Cisco VPN

i'm having the same issues and have tried everything to fix it! any help would be appreciated!

I am having the same issue but am not using the VPN. I've even tried multiple wireless networks to rule out an issue with mine.

We are seeing the same problem on 2.0.1 iPod firmware at our school. Our networking people just upgraded the Cisco security appliance to the 8.04 OS revision specifically to support the iPhone/iPod, too.

We were assuming there was a configuration problem with our VPN concentrator, but I am now beginning to suspect the Apple client. After all, a packet capture of a session between an iPod and the App store shows only ordinary HTTP traffic. What is there to not work?

If your VPN is configured to use the gateway on the intranet (the default) it may be being blocked by the intranet firewall.

I upgraded my iphone to 2.0.1 today and also upgraded itunes to 7.7.1. After doing this i am not able to connect to itunes store either on mac or through appstore on iphone.

what to do 😟

What error message are you getting? Can you access other sites? If you cannot connect on either it sounds like there is something wrong with your iTunes store account.

I have the same issue. Everytime I try to connect to iTunes and App store from the iPhone G3, (now on 2.0.2) a message comes up: "Cannot connect to iTunes". At first I thought it was a problem from my Internet provider, I've been two days on the phone with them trying to fix this but no luck. The most annoying thing is that Safari, Maps and YouTube works great with WiFi. An iTunes Server problem? I also change Wifi router, no luck either. The IPS guy will be visiting today cause they think there is a signal leak (or something like that), I'll post later on that.

BTW Can someone please try connecting WiFi to Internet (Safari) and You Tube to see if we are in the same boat? Thank You.

That makes sense, but an iPod using an open wireless access point on our campus does not have this problem. This open access point also have to got though the intranet gateway, but there is no problem accessing the App Store and iTunes using this configuration.

Out Networking people are quite explicit that they do not block outbound web traffic. Is there some traffic going to the App store that is not HTTP, does anyone know?

sasquatchjr,

Your VPN concentrator also has policies on what traffic to allow through. Essentially its own firewall.

This article explains what host to block to prevent access:
http://docs.info.apple.com/article.html?artnum=93098

Essentially your admin needs to make sure it is possible to reach that site through the VPN.

Hope this helps,

Nathan C.

We're having the same issue. App Store and iTunes do not work when all traffic is tunneled over VPN. Yet, other applications like Safari, New York Times reader, Telnet, etc... work perfectly fine over VPN. If we have the iPhone switch over to using split tunneling VPN mode, then the App Store and iTunes work since they do not appear to be sending traffic over the VPN tunnel. I can say for certain that no outgoing traffic is being blocked on the VPN servers since I administer those servers. I also did a packet capture on the iPhone wireless session and it appears that the App Store sends traffic over the regular HTTP port. So it really doesn't make any sense from a VPN perspective why Safari would work but not the App Store or iTunes when you're tunneling all traffic over VPN. Our iPhones are using the latest firmware (5F136). If anyone has any update, please do share.

Did anyone manage to find a solution to this issue?