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I would like to use a secure VPN configuration in my iPhone (iOS 5.1), to be able to use Internet thru hostile wifi hotspots.

I have already configured an IPSec tunnel to a server I control. I can manually activate the VPN in the phone and be "quite" sure nobody can snoop the WIFI data to/from my phone.

But this scenario has a few problems:

  1. In my VPN, I send a secure DNS configuration to the phone at tunnel creation time. What happen to any DNS record cached?. Is it purged and refetched thru the tunnel?. Leaking DNS data, beside leaking info, can be used as an attack vector AFTER the tunnel is UP and running.

  2. How can I know that ALL data is send thru the tunnel?.

  3. The tunnel must be activated manually. If you forget, you are KO.

  4. If the tunnel breaks, my data is at risk. Since the tunnel can break anytime, including because malicious action, I have to keep a constant eye on the VPN icon. And even if I am fast to stop the data traffic, I am going to leak potentially sensitive data.

Briefly, I would like to be able to use only internet THRU the tunnel. I rather lose Internet service than using the connection with no VPN connection. But I don't see how to do it. Does exist any configuration in iPhone 5.1 to force that ANY internet traffic to go thru a VPN?.

Any advice?.

Thanks!.

migrated from security.stackexchange.com Apr 10 '12 at 22:42

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  • And even worse: what about all the background apps that might send data as soon as your wifi connection is up but before your vpn is connected... – Fuzzy76 Sep 16 at 7:08

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