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A few days ago my cisco gateway router which runs easyvpn started exhibiting strange behavior.

All Apple products (iPads, iPhones, ibook, ietc) have strange traffic issues when connecting to the vpn.

These devices appear to connect ok and are assigned an ip in the subnet 10.49.10.0/27. They cannot ping their assigned ip or any other ip on the network EXCEPT ALL hosts on the 10.49.16.0/24 subnet.

Windows clients work fine!

topology looks like...

╔════╗                                       ╔════╗
║ fw ╟─[192.168.254.253]───[192.168.254.254]─╢ gw ╟─(10.49.10.0/27) Vpn network
╚══╤═╝                                       ╚════╝
   |
[10.49.16.40]
   |
(10.49.16.0/24) Colocation network
   |
   |         ╔═════╗
[10.49.16.3]─╢ rtr ╟─(wan)
             ╚═════╝

The cisco cpn client is used on all platforms.

If any one has any idea what I have done wrong or if you want more information please let me know.

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Does this use the AnyConnect client, or a specific easyvpn program as the client? They've gone through a few... – Bart Silverstrim May 11 '11 at 0:45
Not anyconnect. 'Cisco VPN Client' 5.0.07.0410 is what is used on windows. On the ibook it is the mac version and on the ipad and iphone it seems to be part of the ipsec options for vpn. I will drop another message with more information on the apple clients. – Ablue May 11 '11 at 1:04
Try using the OSX built-in Cisco compatible client, see if the issue remains there as well. – SpacemanSpiff May 11 '11 at 1:10
Still waiting on the end user to respond about trying the builtin client. As a side point the ipad and iphones are using the builtin ipsec clients; while it is branded 'cisco' it doesnt seem to have any version info. – Ablue May 11 '11 at 1:18
looks like the ibook does the same with the builtin software – Ablue May 11 '11 at 1:41
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