Sometimes you need to use Tailscale, but all traffic for the network you’re on needs to passthrough a proxy. There is some conflicting information about this on the wiki and issues pages for Tailscale on Github. See this issue #931.

This can be fixed by adding the following lines to:

/etc/default/tailscaled

If this doesn’t exist for you, check the systemd file at:

/lib/systemd/system/tailscaled.service

# Set the port to listen on for incoming VPN packets.
# Remote nodes will automatically be informed about the new port number,
# but you might want to configure this in order to set external firewall
# settings.
PORT="41641"

HTTPS_PROXY="http://YOUR_ADDRESS:PORT"

# Extra flags you might want to pass to tailscaled.
FLAGS=""

You can try using a username and password, but you will eventually run into formatting errors if the strings aren’t encoded correctly becuase of special characters. If the proxy I am being forced into using requires them, I will setup a local proxy forwarder that doesn’t require a user and pass.

Tailscale --> No auth local proxy --> Auth'd proxy

For this, you can either use the python package pproxy or setup local squid/dante proxy forwarders.