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Mac repeatedly bumped off VPN access to SBS 2008

Posted on 2009-12-21
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I have one MacBook Pro OS 10.6.2 user who only has intermittent access to the server thru VPN.  Our support vendor has already spent way too much time on this and obviously doesn't know what they're doing.  He has lost his VPN user role a couple times for no reason that I can fathom. We're using the native Windows firewall (having disabled the external 3com firewall VPN port)although have since been advised that was a mistake.
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Question by:Martin D
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by:GuruChiu
ID: 26102522
I can try to help, but I need more details on what you mean by:

"has intermittent access to the server thru VPN" - do you mean some times the VPN will work and sometimes it doesn't?

"lost his VPN user role a couple times" - You mean your vendor or the user having this problem? What exactly you mean by "lost his VPN user role". Do you mean the user ID on the server suddenly disappear or you mean something else?
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Author Comment

by:Martin D
ID: 26106996
The user can use VPN for a couple hours and then it will stop working.

On a couple of occasions, the user had to be reinstated in the group Windows SBS VPN Users under user role/account properties.  This happened more than once.

Sometimes rebooting the external firewall has resolved the issue but there remain occasions when it was neither of these fixes worked.
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by:GuruChiu
ID: 26107368
Sorry. No clue. May be some other expert out there can help.
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Martin D earned 0 total points
ID: 26193102
mac guru Reed K suggested trying alternate VPN clients:
http://www.shimoapp.com/

http://code.google.com/p/tunnelblick/
It's a GUI for the excellent OpenVPN client. It's free / open source and it looks like it's even currently maintained.  However, it can be a bit weird.

Viscosity is also a GUI for OpenVPN, but it's a commercial product (costs $9) and looks more stable and more polished.
http://www.viscosityvpn.com/

If I were you, I'd try Shimo first, Viscosity second, and Tunnelblick as a last resort.

Cheers,
Reed.
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