iVPN on Mac OSX 10.4 (Tiger) and 10.6

Update: 22-02-2011

I just updated Mac OSX to 10.6 and the iVPNĀ approach still works, just make sure not to update but stick to the version from this post.

I have a Mac mini with Mac OSX 10.4 (Tiger), and I wanted to use this as my home server. Some kind of VPN server was required to give me external access to my files.

I first read abut iVPN, but I was looking for a free service. I then looked into Hamachi (It looks like LogMeIn har purchased the rights to this software) (HamachiX).

Hamachi

As I understand it, Hamachi was free and multi platform until LogMeIn took over. LogMeIn currently only support Windows, but I needed both Mac and Windows to work toghether.

I then got the latest HamachiX and the free LogMeIn Hamachi2 to work, but the connection kept being dropped after some time. I think it is because HamachiX is based on a legacy version of Hamachi, and LogMeIn Hamachi2 is based on a newer version, and as I do not want to keep loosing my VPN connection, I dropped the idea of Hamachi.

iVPN

Starting from scratch I started to read about other VPN solutions and servers for the client version of Mac OSX. This post explained that a PPTP and L2TP VPN server had been part of all Mac OS since 10.2. It was just not mentioned by Apple nor supported.

This build in VPN server is what iVPN uses (read more in this post), a configuration tool that until version 2.4 was free, but now is commercialware. But as this tool does nothing but configuration, you can download the 2.4 beta version here (iVPN 2.4b).

Configuring the VPN server

As I needed Windows clients to access my Mac mini and due to my current network setup, I chose PPTP as VPN protocol. The following steps explains what I did to setup the VPN server on Mac OSX 10.4.

  1. Download iVPN-2.4b (If you need here is the iVPN 2.4b manual and the iVPN 2.4b source)
  2. Run the iVPN
  3. Click no to the upgrade
  4. Enable the PPTP and disable the L2TP protocol (or enable/disable the protocol you wish to use)
  5. Type in a username and password
    1. Do NOT use spaces in the username…
    2. If you have chosen to use L2TP then write a “shared secret”
  6. Type in a IP address range, but make sure it does not conflict with your existing DHCP server setup.
  7. The router is the default gateway and the subnet mask, normally you would use 255.255.255.0
  8. I used the OpenDNS for DNS resolution.
  9. Check the “Start server at boot time”.
  10. Then click the “On” button.
  11. Type in the administration password if required to.
  12. Close iVPN
iVPN user interface

iVPN application

Firewall

Now the VPN server is setup, now you need to open for port 1723 in the firewall.

  1. Open the System preferences in Mac OSX.
  2. Click “Sharing” under “Internet & network”
  3. Open the “Firewall” tab
  4. Click new
  5. Select other in the “Port name” and write 1723 in the TCP port
  6. As description write PPTP, VPN server or something else
  7. Click ok and then you should be ready Mac OSX wise.

Mac OSX PPTP firewall

Now the only thing left is to open port 1723 in your router. If you have trouble doing that, look into the manual of your router or call the support hotline of your ISP.

About Mikkel Ovesen

I am a .NET developer, primarily developing apps for the web. I have been working with ASP.NET and C# for more than 5 years, and web development for 10 years. I like open-source software and burgers ;)
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12 Responses to iVPN on Mac OSX 10.4 (Tiger) and 10.6

  1. John says:

    Hi. I’ve tried downloading

    http://blog.ovesens.net/wp-content/uploads/2010/01/iVPN-2.4b.zip

    from this page however, the decompression fails. I have tried with two different machines, one running 10.4.11 and the other running 10.5.8 – however I encounter the same error each time.

    Is there some corruption affecting the file I am trying to download?

    Unfortunately I have been unable to location an alternate source for this software – the developer seems to have doon a good job of eradicating it from the web!

    Thanks.

  2. Just a note, I have moved the blog to a new server. And this file has been fixed, a new zip file has been uploaded.

  3. Pingback: Tweets that mention Ā» iVPN on Mac OSX 10.4 (Tiger) Blog of developer Mikkel Ovesen -- Topsy.com

  4. Leo says:

    this post is really useful, I have setup a VPN network and can connect it….

    but I still got some problem.
    my osx 10.6 client cannot read the default gateway setting, it will simply use my man mini as the default gateway…. and
    my win7 machine cannot set the default gate properly.. it just didn’t map to my default gateway setting, so this machine cannot browser other network except the private network.

    is that the program of pptp script? or cause by other reason?

    thx

  5. @Leo: Thanks :)

    I am unsure of what is causing your specific problems, as I would need some more info about your network setup. It would be easier if you could describe your network setup in detail. Are your mac Mini the PPTP VPN server? Is it connected via router to the internet? Are your OSX 10.6 Client and Windows maching connecting to your Mac Mini over the internet? or via the LAN?

    But anyway here are some suggestions.

    Your OSX 10.6 client: You should check “Send all traffic over VPN connection”, this make sure if you use the default gateway of the VPN or not. Have a look here

    Win 7 machine: By default a Windows 7 VPN connections uses the VON connections default gateway (meaning all traffic is routed via the VPN connection). This can cause routing problem when you wish to access the internet. My advice would be to “Disable default gateway”. See more here.

  6. fresis says:

    Hi! Seems like you might be able to help…

    I currently have my Macbook Pro G4 (OSX 10.5.8) setup to 1. be connected to the internet via my airport extreme; 2. have my computer sign into a PPTP VPN; 3. have my airport express connected to the Macbook’s ethernet port; 4. share the internet via the airport express (through internet sharing). This has been working fine.

    However, now would like to try creating the same setup using an older Macbook Pro G3 (OSX 10.4.11). I have the PPTP VPN set up on the G3, but the internet sharing preference panel for OSX 10.4.11 doesn’t have a drop-down for VPN.

    So… how to share the VPN through the airport express via the G3′s ethernet port…?

    Thanks a lot in advance!

  7. @Fresis

    I am not sure about internet sharing on OSX 10.4.11, maybe it is not possible on that version at all.

    This was btw. all I could find http://discussions.apple.com/message.jspa?messageID=8309880

    I hope you can find the reason or a solution.
    Mikkel

  8. fresis says:

    Mikkel:

    Yes, was afraid that OSX 10.4.11 might allow the internet sharing that I was looking for; thought I’d ask the expert, though.

    Many thanks!

  9. Matt Santana says:

    iVPN seems like a potential dream come true. I downloaded it and even installed it despite my apprehensions about being able to do so considering so many other apps that were designed for 10.5 or earlier seem to have a severe aversion to working under 10.6. I cannot get the iVPN server to actually start and I wonder if it doesn’t have something to do with the fact that I am running 10.6.7. Have you seen this issue before and do you know if iVPN 2.4b works with 10.6.7? I have not found any other useful information on this program =\

  10. @Matt

    I am running 10.6.7 and it works fine here. I cannot start and stop the server manually, but set the VPN server to start on boot. Restart the machine and it works, at least here it does.

    / Mikkel

  11. Jeph says:

    Thanks, this is extremely helpful. I have an old Mac Mini (first generation) that I’m running Tiger on, and wanted to see if this would work. Everything goes fine until I turn the VPN server on, at which point it sucks up all available RAM until my machine freezes. Granted, the machine is ancient and only has 256MB of memory, but I’m running nothing else on it and don’t see why VPN services would need much memory.

    Any suggestions for a remedy would be greatly appreciated. Thanks again for the great info!

  12. @Jeph Sorry have not tried the VPN trick on a machine with only 256 MB of ram, and I don’t think it is possible to make it work.

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