How to Connect to PPTP on macOS Sierra Despite Apple’s Support Withdrawal

Starting with macOS Sierra and iOS 10, Apple has withdrawn support for one of the methods of implementing a virtual private networks (VPN), the point-to-point tunneling protocol (PPTP).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.