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On a laptop running Windows 7, I can connect to the VPN server at the office on the Ethernet connection. The VPN server is running on Windows Small Business Server 2011, and I can do it on any other Windows 7 computer in the office.

However, one single computer doesn't let me run the VPN through the wireless connection for long. When it does connect, it disconnects between 5-15 seconds later, asking me to reconnect. I can connect to the VPN via WiFi on my Android phone, and on another laptop, so I know it's not the router.

I also tried disabling the firewall on the laptop in question, with no change. Tried a new WiFi card (internal), and a new WiFi USB adapter. None have fixed the problem.

What else would cause the wireless to not allow a VPN connection?

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Have you tried over ethernet? Is there some mention within system log? – week Nov 15 '12 at 18:05
@week First sentence says I tried with Ethernet. Nothing in the system log that I can see. According to the server, it's the client terminating the connection – Luke Nov 15 '12 at 18:20
You may try something like Wireshark wireshark.org, to intercept a communication and see how it ends? Missed that ethernet, srry... What kind of VPN is that.. pptp? – week Nov 15 '12 at 18:23
@week It's a PPTP. I'll try the WS and see if it sees anything... Weird... happening – Luke Nov 15 '12 at 19:40
probably corrupted OS drivers and/or other Windows system corruption if even replacing the wifi card didn't solve it -try deleting C:\Windows\System32\catroot and C:\Windows\System32\catroot2 and reboot computer does this work? If not, does a complete clean reinstall of Windows OS on that laptop resolve it? – sajawikio Nov 16 '12 at 6:30
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1 Answer

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I ran into this with one laptop about 5 years ago with a coworker. Unfortunately, I wasn't able to debug the problem.

At the time, I was fresh out of my Networking course and my impression was that since it's only occurring over WiFi, that perhaps the laptop is reconfiguring its routing tables periodically, causing the VPN connection to drop. If I recall correctly, when you connect to a network over VPN, the connection persists over a particular route and the VPN server must maintain its own routing table to authorize the connection to the laptop. When you're on a WiFi connection, however, the laptop will have to reconfigure its routing tables more often because the wireless nature of the connection means the network dynamics may change more quickly. I believe that most operating systems are configured to handle VPN over WiFi correctly, but it may be the case that this particular laptop isn't.

Unfortunately, since I wasn't able to attempt a fix, I don't know what to do to fix it. However, this might shed some light on the cause.

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