On Mon, Dec 23, 2019 at 6:28 AM Ross Burton <[email protected]> wrote:
>
> Is there some trick to configuring a macOS proxy so that it is used
> for VPN connections?  Or am I just doing something wrong?

This is *not* a direct answer to your question (I don't run macOS
myself), and apologies as usual for self-promotion, but might I
suggest trying vpn-slice? (https://github.com/dlenski/vpn-slice)

I wrote vpn-slice for situations like yours. It's a replacement for
the usual vpnc-script used by openconnect, making it easy to set up
split-tunnel routing (e.g. routing only specific IP addresses and/or
subnets to a VPN connection), so that the VPN doesn't “steal all
routes” and so that you don't *have to use a proxy*. You use it like
this, specifying individual routes or hosts that you want to go
through the VPN tunnel, and leaving everything else alone:

    sudo openconnect gateway.bigcorp.com -u user1234 \
        -s 'vpn-slice 192.168.1.0/24 hostname1
alias2=alias2.bigcorp.com=192.168.1.43'

Anyway, many other users of OpenConnect are having success with it,
and it now has full macOS support thanks to contributions from macOS users.

-Dan

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