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Consider the following problem, constraints, proposed solution, and questions. Feel free to propose alternatives. Thank you for your help!

Machines

  1. Permanent desktop server running Windows 7 "Home Server"
  2. Cloud virtual-private-server running Ubuntu 10.04 "Cloud Server"
  3. Laptop running Windows 7 "Laptop"

Goal

Setup a VPN system where:

  1. Laptop can access network shares on Home Server when Laptop is roaming
  2. Outgoing Laptop network traffic is encrypted to Cloud Server when Laptop is roaming

Constraints

  1. Home Server is behind several layers of un-accessible and un-modifiable routers. Thus, fixed IP address is not possible on Home Server.
  2. Use native Windows 7 VPN functionality for connections.

Proposed Solution

I plan to setup a VPN server on Cloud Server to receive incoming VPN requests from both Laptop and Home Server. Since Home Server cannot be directly accessed, I am using Cloud Server as an intermediary connection point which Home Server and Laptop can "dial out" to. This should allow Laptop to encrypt outgoing traffic (ie. prevent WiFi snooping). This should also allow Laptop to access network resources on Home Server since they would be apart of the same network on Cloud Server.

Questions

  1. Is this possible?
  2. What specific type of VPN connection do I need?
  3. What special setup do I need on Cloud Server to enabled network resource sharing from incoming VPN connections for Laptop and Home Server?
  4. What special setup do I need on Cloud Server so that Laptop has access to Cloud Server's internet connection when Laptop is VPN'd in?

If you have any other suggestions I'd love to hear. Thanks so much for your help.

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1 Answer 1

up vote 1 down vote accepted

Is this possible?

Yes

What specific type of VPN connection do I need?

You might be able to use PPTP if the NAT routers support the appropriate passthrough - there are walkthroughs on that topic for Ubuntu on the net. Or set up IPSEC/L2TP - which has NAT traversal "built in" and needs just UDP to work. Walkthroughs available as well.

What special setup do I need on Cloud Server to enabled network resource sharing from incoming VPN connections for Laptop and Home Server?

Basically, IP connectivity is sufficient. You would need to enable routing and make sure you are not filtering your own traffic.

What special setup do I need on Cloud Server so that Laptop has access to Cloud Server's internet connection when Laptop is VPN'd in?

The "use remote gateway when connected to the VPN" setting is a default in Windows clients and needs to be disabled explicitly, if you don't want it.

If you have any other suggestions I'd love to hear

If you can drop your second requirement, I'd really recommend OpenVPN - it is easier to debug and maintain and offers more connectivity options that you might need one day.

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I want to vote you up but I cannot because I do not have 15 rep yet on SF :( –  Mike Knoop Sep 24 '11 at 17:20
    
@MikeKnoop I upvoted on your behalf. Of course, if you stick around and ask more good questions / give some good answers that rep issue will take care of itself. =) –  Wesley Sep 24 '11 at 19:13

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