Apple killed off its support for PPTP VPNs when it released OS X in September of 2016. There was one application we had to maintain where the only way to connect and update it was via this out-of-favor protocol. Here’s how to get in and get the job done over PPTP one last time.

The Problem

PPTP on Mac OS X. This step-by-step tutorial shows how to setup a PPTP connection on Mac OSX Lion. Warning: Please be aware that PPTP has been considered insecure for a few years already and we don't recommend to use it for anything sensitive. It is a good choice for geo-unblocking, but nothing else if privacy and security are top priorities. Apr 13, 2017; Manual Configuration for PPTP protocol on Mac 1. Click on the 'apple' logo and select 'System Preferences'.2. Click on 'Network'.3. Click on '+' sign to add the VPN connection. Click on 'Interface Menu' Insert the following info: Select VPN from Interface drop down menu; Select PPTP from VPN Type drop down menu; Insert Service name as OneVPN (PPTP). Setup PPTP VPN on Mac OS X. To setup PPTP VPN on Mac, first, open the “System Preferences” by going to the Apple menu. Next, click on the “Network”. In the “Network”, there is a list of network connections on the left side. Click on the “+” icon (highlighted in red) to.

First, credit for this solution should go to the following post: https://smallhacks.wordpress.com/2016/12/20/pptp-on-osx-sierra/

Pptp Client For Mac Os

We only had to make a couple of tweaks to the ppp configuration provided on that page in order to get the job done and they’re likely specific to our circumstances.

Second, you should really get off of PPTP VPNs as soon as practicable. The most common authentication protocol used on them, MS-CHAPv2, has been known to be vulnerable to attacks since 1999 and in 2012 Moxie Marlinspike released a tool that could be used in combination with a brute force attack to decrypt traffic over the VPN tunnel.

So, make plans to retire that VPN now and move to an IPSec or SSL VPN.

Write the following file to /etc/ppp/peers/pptpvpn:

The Modifications

We had to add the following lines to the configuration to help connect to our client’s network:

We encountered errors related to Extensible Authentication Protocol, turning it off allowed us to move on.

It was useful to turn on debugging to trace down the cause of one particular issue. At one site, the configuration requests being sent were not being acknowledged. After 10 unacknowledged requests, the connection was dropped. So turn on debugging and you should see requests and acknowledgements as well as messages detailing the authentication process.

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The likely cause of the unacknowledged requests was that the router we were communicating through didn’t support Generic Router Encapsulation (GRE). Captive portal for mac. Since we did not control that router, there was nothing to do but move to a site that we could communicate from.

Connect to the VPN by running:

After Connecting

When you connect successfully you should get a response like this in your terminal:

What you will need to do next, in order to make sure you’re not just sending requests out of the wrong interface, is to add a route to the host you need to contact on the other network:

Pptp For Mac Os High Sierra

Then you should be able to browse, ssh, ping, or do whatever you need to with the host on the other side.

Well I could just buy a VPN client…

Fair enough. There are two vendors for VPN clients for OS X supporting PPTP. One client costs $50 and the other vendor offers their software as an annual subscription. Unfortunately, buying new software doesn’t deal with the fact that PPTP should be phased out. Save your money, use the underlying ppp client in OS X to get connected, and then plan on replacing that old protocol.