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My employer has given me a VPN connection. It does not work on my laptop, but if a family member sets up the exact same connection on their machine (same network), then it works fine.

By 'broken', I mean:

  • The VPN connection does get established, without errors.
  • browse to any website: timeout
  • ping 1.1.1.1: timeout
  • ping 8.8.8.8: timeout

We've tested this connection on several machines:

  • My work laptop / my home network → broken
  • My work laptop / via mobile data → broken
  • My private laptop / my home network → broken, except that browsing to a site that requires VPN now works
  • A VM (this one) on my work laptop / my home network → works
  • A colleague's laptop / their home network → works
  • A family member's laptop / my home network → works

The only constant between all of the failures is that all the broken machines are mine. I probably do something to my machines that breaks this VPN. I wish I knew what.

What baffles me most is that the VPN can be functional in the guest OS, but broken in the host OS. If the host OS somehow breaks the VPN, wouldn't that affect the guest OS as well?

The VPN server is an Algo VPN running on DigitalOcean.
The VPN client is the built-in Windows 10 VPN client.
The VPN is configured to tunnel traffic to pretty much anywhere through the VPN - we've configured numerous services to only accept traffic from the VPN IP.

Does anyone understand VPN on Windows 10 enough to figure out which component is at fault here?

VPN client screenshot

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    Ask your Work Support if they can determine why this does not work for you. Ask them how to enable logging so you or them can determine where the connection fails.
    – John
    Jun 2, 2020 at 22:42
  • Good point. I have discussed this with the person in charge of the VPN server. Results: 1) they tried the same connection on their Win10 machine, and it worked fine there. 2) They can see me establishing the VPN connection successfully, no errors there. 3) They don't know where on my machine the issue is, they advise reinstalling Windows.
    – Grilse
    Jun 3, 2020 at 0:39
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    You can first try a Windows 10 Repair Install and Keep Everything. If that does not work, same process, Keep Documents and Data but reinstall your software. Easier than a fresh install. Use the Microsoft Media Creation Link.
    – John
    Jun 3, 2020 at 0:43
  • Ate you running any local virus / malware protection? Maybe this us intercepting and denying the traffic.
    – davidgo
    Jun 3, 2020 at 8:02
  • Antivirus: yes, but not the same one both laptops. One uses F-Secure, the other uses Windows Defender Antivirus.
    – Grilse
    Jun 3, 2020 at 8:17

1 Answer 1

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After uninstalling F-Secure, the VPN connection works.

It seems that network connections on the guest OS (i.e. from the VM) bypass any software firewalls on the host OS.

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