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Okay, first our setup:

I'm currently working over VPN to a mac mini OSX 10.6 server. We have a testsetup VM running on that, using ubuntu 12.04.

Earlier today, there was an outage because of which our mac mini server was reset. Since then, i was unable to initiate a connection to the VM (which i did boot) -- no ssh, no web, ... . I couldn't ssh or web from the mac mini to the vm either. I could do so from within the VM itself, though. Ping did work on all machines.

Lastly, I tried pinging from the VM to my laptop. It took a moment, but then it finally started to ping (no timeouts or so). After that, web and ssh magically worked.

I then didn't use the machine for about 5 minutes, after which i had to ping from the server to my laptop again before i could setup a connection.

I'm in the dark on what this could be, though I think this is something to do with lookups.

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You should provide more details on the virtualization solution used. Aside from that, your symptoms sound like an L2 micsonfiguration. Do you have an accidental network loop of some kind in your network? Do you have the VLAN memberships right there? Do you have a duplicate MAC address within your network? A network trace along with the switch's MAC address database might help diagnosing this issue. – the-wabbit Oct 1 '12 at 9:07
Sounds like your VPN client is timing out, but not realising it's timed out until there's some actual traffic going through. Please provide details about what VPN solution you're using if you want more specifics. – Per von Zweigbergk Sep 28 at 19:37

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