Jan 01, 2017
iOS OpenVPN VPN On Demand | Sean Ryan Nov 23, 2017 Setting up a UniFi Security Gateway for an On Demand iOS VPN May 18, 2020 Top Mac VPN to Use in 2020 [An Updated 2020 List]
At least on Sierra, it is possible to create a VPN on demand profile (mobileconfig file) as for iOS (reference here), and import this into macOS. After that, a VPN connection will appear in the network settings with an on-demand checkbox. However, it does not seem to work exactly as expected.
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How to Connect Your Mac to Any VPN (and Automatically Jun 18, 2019 accessing windows network drive over vpn - Apple Community Dec 09, 2008 VPN on Demand | MacRumors Forums Jun 06, 2010