Usability issue in MacOS

Yoni Leitersdorf litelite at
Sat Feb 8 22:51:39 CET 2020

The original concept behind "On Demand" is to trigger the VPN when it's
needed - specifically when specific domains are being accessed. Indeed,
Apple expanded it to even include interfaces that are connected, SSIDs,
etc, in a non-intuitive way.

However, what makes it somewhat more un-intuitive is the fact that these
checkboxes appear in the main configuration screen for the tunnel. So, one
just simply checks the boxes, thinking "I want VPN to work on-demand on all
of my interfaces". Since, this feature works so oddly (compared to its
name), I would recommend putting it under a separate dialog. In that
dialog, we can explain what this feature does, and also allow for DNS names
to be used, which is the main use case for VPN On Demand.

On Sat, Feb 8, 2020 at 1:37 PM Jason A. Donenfeld <Jason at> wrote:

> Talk to Apple about that:
> I'm hesitant to stray too far from the analogies that they set up,
> even if this is geared toward developers, because inevitably people
> start googling, and I'd rather them find what they're searching for.
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