I have spent the last two days searching for answers. I have a rather odd situation that I am trying to work with.
Click on Authentication Settings and enter your My Private Network Password in the Password field, click OK. Apple OSX PPTP VPN authentication settings.
I have a PPTP vpn server hosted on Win 2008 R2 and I am able to connect and browse the internet over the tunnel, however my problem is that I have an iboss web filter that relies on MAC addresses to apply the correct filtering. So when I connect, the client shows up on the iboss as the server's mac. I dont have any filtering enabled on the VPN server and thus the clients internet traffic is unfiltered. Is there anyway to get the VPN server to use each individual computers mac as it accesses the internet so that I can place all of the computers into the correct filtering group?
I have no idea how you pass through the mac address on a pptp tunnel. However, I think a couple of points may be worth considering:. If your clients have split tunneling enabled, their traffic will be unfiltered anyway, as their internet traffic will use their internet connection, not yours. Unless you have control over the client machines, the users can enable split tunneling without your knowledge and approval - thus bypassing your filter even if you do get it working. split tunneling makes for much faster end user experience as they don't need to use the slower pptp tunnel except for traffic to/from your lan.
I know that some security pundits reckon split tunneling is insecure, but unless you have total control over the end user's machine, and it is never connected to the internet except via your tunnel, it seems to me that the risk of 'unclean behaviour' by the client exists irrespective of whether you allow split tunneling. So, my assessment would be like this:. When the end user is not connected to my PPTP tunnel, I have no control over their internet traffic or their download behavior. the end user is only connected to my PPTP tunnel for a portion of the time.
Therefore, I gain nothing by forcing them to use my PPTP connection for all traffic while they are connected to my PPTP. I don't want them using my PPTP connection for unfiltered internet connectivity, as then their porn site browsing is happening through my corporate network.
So - Enable split tunneling on the client, then no internet browsing will go through the PPTP tunnel, and then you don't have to worry about trying to filter it!
You've gone ahead and have (Virtual Private Network) service and have that suits your needs. You connect to it, that's what! And here's how you do it on your Mac. How does your VPN provider require you to connect to their servers? There are two main ways of connecting to your VPN service provider. Either by using the macOS built-in networking framework, or by using the VPN provider's own connection application.
How to Connect to the VPN when no third party app is provided. Click on the Apple icon in the upper left corner of your Mac's screen.
Click on System Preferences. Click Network. Select VPN from the interface drop-down list. Select the VPN Type provided by your VPN service provider. In our example, we are using L2TP over IPSec. Type in a Service Name that is easy for you to recognize when you want to connect. Click Create.
Type in the Server Address that the VPN service provides you. It may be in the form of an IP address or a Hostname. Type in your Account Name (also provided by your VPN). Click Authentication Settings. The type of VPN encryption being used by your VPN provider will determine what sort of authentication settings you will need to enter. Select the User Authentication method you have been given by your VPN provider and enter the pertinent details.
In our example we will be using Password. Select the Machine Authentication required by your VPN provider and enter the pertinent details. In our example, we are using a Shared Secret. Optionally, you can check Show VPN status in the menu bar if you want to be able to quickly enable and disable your VPN connection from the desktop. Click Advanced.
Check Send all traffic over VPN connection to be able to encrypt all of your internet access through the VPN provider. You can check out the. Click Apply.
Click Connect to start your VPN Connection. Other resources If you'd like to get more information on VPNs, VPN service providers, or simply want to get into more detail on how VPNs function, the folks at have an extensive, easy to navigate, and comprehensive look at VPN solutions. Any questions? If you're anything like me (and if you've read our series of VPN and macOS Server articles thus far) then privacy and security are high on your list of priorities. Now that you're surfing more securely, let us know what service you chose and why in the comment section below!