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Attention: don't use Docker's own GUI to set the proxy!

See https://github.com/docker/for-mac/issues/2467
In Docker > Preferences, in Resources > Proxies, make sure you're NOT using manual proxies
Use the hack below to set the environment var directly in LinuxKit
The issue is that setting it in the GUI affects containers too (!!!), and we don't want that in this scenario
If you actually need an upstream proxy (for company proxy etc) this will NOT work.

Using a Docker Desktop for Mac as a client for the proxy

First, know this is a MiTM, and could break with new Docker Desktop for Mac releases or during resets/reinstalls/upgrades.

These instructions tested on Mac OS Catalina, and:

Docker Desktop for Mac 2.4.2.0 (Edge) (which provides Docker 20.10.0-beta1)
Docker Desktop for Mac 2.5.0.0 (Stable) (which provides Docker 19.03)

This assumes you have docker-registry-proxy running somewhere else, eg, on a different machine on your local network.

See the main README.md for instructions. (If you're trying to run both proxy and client on the same machine, see below).

We'll inject the CA certificates and the HTTPS_PROXY env into the Docker install inside the HyperKit VM running LinuxKit that is used by Docker Desktop for Mac.

To do that, we use a privileged container. justincormack/nsenter1 does the job nicely.

First things first:

1) Factory Reset Docker Desktop for Mac...

... or make sure it's pristine (just installed).

Go into Troubleshoot > "Reset to Factory defaults"
it will take a while to reset/restart everything and require your password.

2) Inject config into Docker's VM

For these examples I will assume it is successfully running on http://192.168.1.2:3128/ -- change the export DRP_PROXY as appropriate. Do not include slashes.

Run these commands in your Mac terminal.

set -e
export DRP_PROXY="192.168.66.100:3129" # Format IP:port, change this 
wget -O - "http://${DRP_PROXY}/" # Make sure you can reach the proxy
# Inject the CA certificate
docker run -it --privileged --pid=host justincormack/nsenter1 \
  /bin/bash -c "wget -O - http://$DRP_PROXY/ca.crt \
 | tee -a /containers/services/docker/lower/etc/ssl/certs/ca-certificates.crt"

# Preserve original config.
docker run -it --privileged --pid=host justincormack/nsenter1 /bin/bash -c "cp /containers/services/docker/config.json /containers/services/docker/config.json.orig"

# Inject the HTTPS_PROXY enviroment variable. I dare you find a better way.
docker run -it --privileged --pid=host justincormack/nsenter1 /bin/bash -c "sed -ibeforedockerproxy -e  's/\"PATH=/\"HTTPS_PROXY=http:\/\/$DRP_PROXY\/\",\"PATH=/' /containers/services/docker/config.json"

3) Restart, test.

Restart Docker. (Quit & Open again, or just go into Preferences and give it more RAM, then Restart.)
Try a docker pull now. It should be using the proxy (watch the logs on the proxy server).
Test that no crazy proxy has been set: docker run -it curlimages/curl:latest http://ifconfig.me and docker run -it curlimages/curl:latest https://ifconfig.me both work.
Important: pushes done with this configured will either not work, or use the auth you configured on the proxy, if any. Beware, and report back.

Using Docker Desktop for Mac to both host the proxy server and use it as a client

@TODO: This has a bunch of chicken-and-egg issues.

You need to pre-pull the proxy itself and justincormack/nsenter1.

Follow the instructions above, but pre-pull after the Factory Reset.

Do NOT use 127.0.0.1, instead use your machine's local LAN IP address.

Make sure to bring the proxy up after applying/restarting the Docker Engine.

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