Updated 06/17/2011: Before you get too far into this post I wanted to point out that I didn’t find a solution to getting a PPTP VPN connection to work with my AirPort Extreme Base Station. I switched over to using L2TP instead.

Updated: 08/03/2011: I’m moving to a different solution to bring PPTP back to my network setup, but you won’t like it. The step I’ve taken illustrates how inconvenient this problem can be.

Overall, I really like the new Airport Extreme Base Station that I purchased recently. The only problem I’ve had, and unfortunately it’s a major problem, is a loss of the ability to connect back into my network remotely over PPTP  via Windows 7 (I prefer to connect to my VPN when staying in a hotel).  I forwarded the appropriate ports but I was only able to use my network for about 20 seconds at a time. After that time was up I could no longer do anything on the network and the connection would usually close within a minute or two.

Unfortunately, I haven’t been able to find a true solution to this problem but I did find an acceptable work-around. I suspect this is a problem with the Extreme not properly passing the PPTP connection, though I don’t know for certain.

I started looking at using other VPN servers. Previously, I just had Windows 7 configured to accept VPN connections. I tried OpenVPN via a VMWare appliance in Fusion, but aside from configuration issues the larger problem was that I could not connect to the VPN using my iPhone or iPad.

My solution, which seems to have worked, was to purchase a copy of MacServe’s iVPN and move the VPN handling directly into OS X. Cost in USD was around $25. It hooks into existing OS X software but provides a simple GUI for management. This option turned out to be very easy to manage and works with all of my devices. Rather than using PPTP I moved over to L2TP.

On the Airport Extreme I setup three UDP ports to forward to a specific system within my network: 500, 1701, 4500

Currently, it sounds like OS X Lion may include similar capabilities, but I simply could not wait until the release of Lion.

Apple, Home Networking, OS X, Projects, Software, Tips, Windows
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Join the conversation! 7 Comments

  1. […] any other devices. The only major problem I had was remoting in over VPN/PPTP to a Windows machine, though I found a work-around that has been performing perfectly since implemented. Since I have a mixed environment with both OS X and Windows I was able to solve the problem but […]

  2. […] in the process of shifting these functions over to it. Most of the software is working, with the exception of the VPN server. The home automation system is not running under my license of mControl 2, but instead using the […]

  3. […] know the AEBS is the problem. PPTP worked fine before I added the AEBS and it also works […]

  4. Hey, just read this and noticed you were talking about the PPTP passthrough issues through the router. I recently investigated PPTP passthrough to find exactly how it works and why it causes problems with routers. Take a look at it, you may find how to solve it yourself after reading it.

  5. […] WL-520GU Wireless Router by Michael on August 14, 2011 A while back I discovered that the Airport Extreme Base Station wouldn’t properly handle an incoming PPTP VPN connection. Recently, because I moved my home automation setup to an ASUS EeeBox PC, I decided to switch back […]

  6. […] router and wireless access point. Though initially impressed, I learned that this expensive device wasn’t capable of fully permitting incoming PPTP VPN connections. In addition, it didn’t provide many configuration options. To work around this problem I […]

  7. […] setup an L2TP VPN server on the iMac again and was able to re-use my Vitamin D Video Pro license with OS X. Setting up home […]


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