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Possible solution for iChat connection problems over VPN System 10.7
This is very specific but I offer it as it may help others.

Since upgrading to 10.7, using a VPN with manually set split routing, iChat does not connect.

I have a setup whereby I connect to work via (Cisco) VPN configuration. After connecting I modify the routing tables so that only the required traffic goes via the vpn tunnel; the default route is set to the Internet gateway.

Since upgrading to 10.7 I have found that upon connecting and modifying the routes, iChat goes offline and won't reconnect.

I happened upon a solution which is to change the IPv6 settings from Automatic to link-local only. This setting is changed in the Advanced section (TCP/IP) of the Network System Preferences for the active Primary Interface (Wi-Fi in my case, but it would be equally applicable to any).

I cannot say with complete certainty that this is the cause but (a) as soon as I changed the IPv6 setting iChat went back to online, and (b) my routing table changes are only made to IPv4 addresses, and if iChat is using IPv6 in some sort of internal 6-to-4 tunnel then this change would make sense.

I reserve the option to be wrong about the actual cause.

[kirkmc adds: I have no way of knowing whether this is correct. I've had the occasional problem with iChat not connecting (not using a VPN), and publish my solution as this hint.]
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Possible solution for iChat connection problems over VPN
Authored by: prachigauriar on Jun 14, '12 08:30:11AM

I have this same problem, so Iíll try it when I get home from work.

In addition to this and kirkmcís hint, I have found that with the Messages beta, the way to get around these sorts of problems is to go to the Accounts pane of iChat/Messageís preferences and just disable/re-enable the affected accounts. Seems to work pretty well, annoying as it may be.



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Possible solution for iChat connection problems over VPN
Authored by: vrosso on Jun 14, '12 11:02:16PM

I've tried setting up custom routes for the built in Cisco VPN client but haven't been successful. How did you do it?



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Possible solution for iChat connection problems over VPN
Authored by: petergort on Jun 15, '12 03:02:15AM

I found a simpler way was to simply modify the service order. (Network settings, click on the little gear icon and 'set service order'). I put the interface to the internet (wifi or ethernet depending on where I am) as first in the list, and the VPN interface down from that. If you are vpn'ing into a private address range subnet that is different from your own, then it just works anyway. If the subnet you are vpn'ing into has the same private address range, then I use 'sudo route add destinationip vpnrouterip' to define a path to where I want to go. I have these 'route add' commands saved as applescripts in my scripts menu, making it quick and simple to use. And because the primary interface is going to the internet, any app launched that isn't trying to reach the VPN destination will automatically go out that interface by default.



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Possible solution for iChat connection problems over VPN
Authored by: agentx on Jun 16, '12 10:01:52AM
Also networksetup command comes in handy for disabling IPv6 on an interface. I have to do this at some Active Directory sites.
sudo networksetup -setv6off Ethernet or Wi-Fi
Edited on Jun 16, '12 10:02:34AM by agentx


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Possible solution for iChat connection problems over VPN
Authored by: withinavoid on Jun 19, '12 10:04:10AM

I've had the same problem. Each time this happens I have to go to Accounts -> Server Settings -> and check or uncheck SSL to get it to reconnect. Strange issue. I'll try to disable and enable account next time.



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Possible solution for iChat connection problems over VPN
Authored by: Ralph Johns on Jun 19, '12 11:41:13AM
Hi,

iChat Needs to have only one Internet Connection so that Audio and Video Chats work. When you "Share" a Neighbour's WIFI as well as using Ethernet yourself you get two connections to the Internet.
In Leopard there is an issue with a Computer doing Internet Sharing and iChat and iChat can "See" the second computer's Internet connection

For a long time on the Apple Discussion Boards we have been suggesting that IPv6 be turned Off (where it is active at the ISP end) so that you only have one connection. In Lion IPv6 can not be fully turned Off and you have to use the Local Link option
---
Ralph Johns
Ferndown
Dorset
Great Britain


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