How to restore PPTP VPN Access back to Mac OS Sierra

If you’ve recently upgraded to Mac OS Sierra you may have noticed that your VPN settings have been deleted during the upgrade process. Upon trying to enter the VPN settings again you may notice that there is NO PPTP option. Unfortunately Apple has removed the PPTP client from Mac OS Sierra due to PPTP lacking the security features of other VPN protocols.

• MacOS 10.15 Catalina macOS 10.14 Mojave macOS 10.13 High Sierra macOS 10.12 Sierra OS X 10.11 El Capitan OS X 10.10.5 Yosemite OS X 10.9.5 Mavericks. Included: all future updates through the VPN Tracker 365 plan; VPN Tracker World Connect integration; the ultimate VPN client for Mac download version for now and the future; Free Trial.
• Oct 15, 2019  I have now upgraded to macOS Catalina and my VPN L2TP is no longer working. Is it something to do with racoon / vpnd service that needs to be replaced on the Mac? Appreciate any help on this please. As a backup I’m running Ubuntu on VMware fusion which accepts VPN connections and clients can successfully connect to it.

As stated by Apple:

If you’ve set up a PPTP VPN server, iOS 10 and macOS Sierra users won’t be able to connect to it. iOS 10 and macOS Sierra will remove PPTP connections from any VPN profile when a user upgrades their device.

PPTP VPN on Catalina Quick question, is there any way to use a PPTP VPN on Catalina? I read that Catalina does no longer natively support PPTP, but is there any free working alternative client that i could use?

Even though PPTP protocol is still available on iOS 9 and earlier or OS X El Capitan and earlier, we don’t recommend that you use it for secure, private communication.

For those who this has come as a surprise and need to regain PPTP VPN access on Mac OS Sierra you’ll need to use a third party VPN Client to regain access to your PPTP servers. Below is a list of PPTP VPN Clients for Mac OS Sierra which will restore PPTP VPN access back to your Mac:

1. Shimo VPN – Free Trial Available

As we find more PPTP VPN Clients we’ll update this list

Update: 7/10/16. We are still looking for other PPTP VPN Client alternatives for macOS Sierra but we haven’t been able to find any either paid or free. At this point Shimo VPN is the only one we can find available. If you know of any others please let us know in the comments.

Applies to: MacOS Sierra

Please Note: This is a “QUICK SUPPORT” article. The information contained herein is provided as is. As a result of the speed in making it available, the materials may include typographical errors and may be revised at any time without notice.

Starting with macOS Sierra and iOS 10, Apple has withdrawn support for one of the methods of implementing a virtual private networks (VPN), the point-to-point tunneling protocol (PPTP). Even though the protocol is still available in earlier versions of its mobile and desktop software, Apple has dropped support for PPTP for security reasons. In other words, if you have set up a VPN server using PPTP, iOS and macOS Sierra users will no longer be able to connect to it. iOS and macOS will display an error message informing users about the security risk that a connection via PPTP represents, and the only option users have is to select “OK”. That, however, doesn’t mean they will connect to the VPN server.

Why Apple Dropped Support for PPTP

Apple has rightfully made this move due to the fact that PPTP has failed numerous security analyses in which serious security vulnerabilities in the protocol had been discovered. Actually, even Microsoft, the creator of the protocol, recommends not using PPTP or MS-CHAPv2 (Microsoft Challenge Handshake Authentication Protocol version 2). The latter is widely used as an authentication method in PPTP-based VPNs. Microsoft's security advisory document released in 2012 talks about the issue caused by known cryptographic weaknesses in the MS-CHAPv2 protocol that allows hackers to exploit its vulnerabilities to obtain a user’s credentials.

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Apple Recommends Using More Safe Protocols

In a support document updated in mid-2017, Apple suggests users deploy other, more secure protocols for user-based authentication, such as L2TP (Layer To Tunneling Protocol), IKEv2 (Internet Key Exchange version 2) and IPSec (Internet Protocol Security), and even mentions several SSL VPN clients available in the iOS App Store. IPSec is a set of protocols used to secure internet traffic that provides much stronger security than PPTP, while IKEv2 is more secure than IPSec since it supports AES 128, AES 192, AES 256 encryption. Because L2TP doesn’t provide strong encryption or authentication by itself, in most cases it is implemented along with IPSec.

The side effect of withdrawing support for an insecure and outdated protocol is that Apple is (finally) forcing users of its latest mobile and desktop operating systems – as well as operators of VPN systems – to take the step toward a more secure internet browsing experience.

How to Connect PPTP VPN on macOS Sierra

While it is still possible to connect to a VPN over PPTP on macOS Sierra, it is not recommended to do so if you really want to protect yourself from cybercriminals. But sometimes there is no choice, of course, and you’ll need to connect to VPN via PPTP despite its insecurities, but until the VPN access service gets upgraded to support safer protocols this is unavoidable.

For those who just can’t part with the protocol just yet, the good news is you have various options to connect via VPN clients that still support the outdated protocol. One of them is Shimo, which costs $50 per user, but offers a 30-day free trial to test the service. To make it work, create a new PPTP/L2TP account and simply follow the instructions, and you’ll be good to go. However, Flow VPN does the same for free. This client supports both PPTP and OpenVPN on macOS Sierra; just overwrite the Flow VPN server address with any server, and make a connection.

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