I have two servers running Windows Server 2008 R2 which are connected via a VPN tunnel. The connecting server uses the built in VPN client from Windows (using rasdial on boot). The VPN Server is supplied by the Firewall (Sophos/Astaro UTM 9) on the other side not by the second Windows server.

Now I have the problem, that sometimes the connection gets closed of different reasons and then I allways manually reconnect the VPN which is not very good practice.

So I am searching for a tool, which can e.g. ping my second server every minute and if not reachable tries to reconnect the VPN.

Does someone know such a tools?

  • Please explain the downvote so I can improve? Jun 1, 2013 at 7:22

2 Answers 2


Do you know the reason why it drops out? Would hunting the source of the issue rather than applying a hacky solution not be a wee bit better? :)

However, that aside, have a look at this document VPN Reconnect?


VPN Reconnect is a new feature of Routing and Remote Access Services (RRAS) in Windows® 7 or Windows Server® 2008 R2 that provides users with seamless and consistent VPN connectivity, automatically reestablishing a VPN when users temporarily lose their Internet connections.

Failing that - How are your programming skills :) If you want to explore your ping option it wouldnt be too hard to write a simple program to do this. I'll point you to an answer somebody submitted on stack overflow. I would take an approach similar to this.

Granted this isnt a programming question but just putting it out there for reference.

  • One of the reasons it drops out is, because the connection is sometimes "away" for a few seconds and thats out of my hands. I already thought of writing my own tool, but just wanted to ask first, if there is already something out there... Jun 1, 2013 at 7:23

Per the [Microsoft Doc]9http://www.microsoft.com/en-us/download/details.aspx?id=20277),

Creating and Configuring the Remote Connection with VPN Reconnect on CLIENT1 On CLIENT1, you use Network and Sharing Center to create a connection to vpn1.contoso.com and save the connection. You then configure the properties of that connection to use VPN Reconnect.

To create the VPN Reconnect connection to vpn1.contoso.com

  1. On CLIENT1, click Start, and then click Control Panel.
  2. Under Network and Internet, click View network status and tasks.
  3. In Networking and Sharing Center, click Set up a new connection or network
  4. Click Connect to a workplace, and then click Next.
  5. Click Use my Internet connection (VPN).
  6. Click I'll set up an Internet connection later.
  7. In Internet address, type vpn1.contoso.com. In Destination name, type VPN Reconnect Connection and then click Next.
  8. In the Type your user name and password dialog box, type the following information: In User name, type user1. In Password, type Pass@word1. Click Remember this password. In Domain, type contoso.
  9. Click Create, and then click Close.

To configure and test the VPN Reconnect Connection

  1. On CLIENT1, in Network and Sharing Center, click Change adapter settings.
  2. Double-click VPN Reconnect Connection, and then click Properties.
  3. On the Security tab, in the Type of VPN list, select IKEv2, and then click OK.
  4. In the Connect VPN Reconnect Connection dialog box, click Connect.
  5. If the Set Network Location dialog box appears, select Work. CLIENT1 should successfully connect to VPN1 using the VPN Reconnect connection. To verify the connection, access the corporate file server from the CLIENT1 using the VPN Reconnect connection you just set up.

To test the remote connection by connecting to a remote file share

  1. Click Start, click All Programs, click Accessories, and then click Run.
  2. Click Start, type \dc1.contoso.com\corpdata, and then press ENTER.
  3. Double-click VPNTest to open it, add some text, and then save the file.
  4. Close Notepad.
  5. In the Network Connections window, right-click VPN Reconnect Connection, and then click Disconnect.

Not the answer you're looking for? Browse other questions tagged .