macos – How to connect OS X Yosemite to a Windows based SSTP VPN?

As others pointed out the best way would be to install sstp-client but iSSTP can also work, however note the following:

1. You need to ensure you get the latest version (1.0.15 currently) as 1.0.14 has a bug and does not work.
2. If you use iSSTP ensure you replace their bundled sstpc file (Contents/Resources) with the latest from where you installed it (/usr/local/Cellar/sstp-client/1.0.15/sbin)

So,

Install with brew install sstp-client

Run:

sudo /usr/local/Cellar/sstp-client/1.0.15/sbin/sstpc --password *** --user *** <host>

For PAP I use the following command:

sudo /usr/local/Cellar/sstp-client/1.0.15/sbin/sstpc --password *** --user *** <host> noauth defaultroute require-pap

In iSSTP (once you replace their old binary) ensure you set the pptp options in advanced (see here: https://linux.die.net/man/8/pppd)