How do I access a docker insecure registry from a Windows docker on Windows 10 machine?

I have 2 machines running dockerd. One an Ubunto.18.04 box with docker version 18.06.1-ce installed, which I want to use as an insecure test registry/repository server where the only way I'll use it is to use a SSH tunnel in to port 5000.

The other is a development workstation, a Windows 10 'pro' box which also has a local instance of docker (docker for Windows version 18.06.1-ce) running as a service on it which I am using to build test images.

So far I can't get the Windows box to push to or pull from the Ubuntu box through the tunnel.

Both dockerds are running. I added the insecure registries setting on the workstation ( via the docker GUI, I could not find the daemon.json file so assume it is in the Windows registry or a hidden location?)

I added localhost:5000 to test for using the SSHE tunnel and Dev2:5000 (temporary for this test opened port 5000 on the internal subnet) to test a direct connection without the tunnel, and restarted docker.

On the registry box I followed the sample of how to use a private registry and did the below to test it. I was logged to "Dev2" as a user I added to the "docker" group that also has sudo privileges. I also tried as root.

Dev2:> docker pull ubuntu:18.04# successDev2:> docker tag ubuntu:18.04 localhost:5000/testapp:00.01Dev2:> docker push localhost:5000/testapp/00.01# successDev2:> docker tag ubuntu:18.04 Dev2:5000/testapp:00.02Dev2:> docker push Dev2:5000/testapp/00.02# successDev2:> docker image rm ubuntu:18.04# successDev2:> docker image ls -aREPOSITORY               TAG                 IMAGE ID            CREATED             SIZElocalhost:5000/testapp   00.01               ea4c82dcd15a        40 hours ago        85.8MBDev2:5000/testapp        00.02               ea4c82dcd15a        40 hours ago        85.8MBregistry                 2                   2e2f252f3c88        5 weeks ago         33.3MBDev2:> curl http://localhost:5000/v2/_catalog{"repositories":["testapp"]}Dev2:>  curl http://localhost:5000/v2/testapp/tags/list{"name":"testapp","tags":["00.01","00.02"]}Dev2:> curl http://Dev2:5000/v2/_catalog{"repositories":["testapp"]}Dev2:> curl http://Dev2:5000/v2/testapp/tags/list{"name":"testapp","tags":["00.01","00.02"]}

At this point all seems to be fine. If I delete the images on the Dev2 docker and pull them they are extracted from the repository and re-added to the docker instance.

Now I try to pull the images into docker on the workstation.

I run a ssh tunnel ssh on the Windows 10 workstation ( Msys GNU version)

workstation:> ssh nyc.livingwork.com -L 5000:localhost:5000 &  # this runs and the tunnel workstation

I also try using a browser (no curl here) with URLs:

http://Dev2:5000/v2/testapp/tags/listandhttp://localhost:5000/v2/testapp/tags/list

And I get for both:{"name":"testapp","tags":["00.01","00.02"]}

So the server is accessible both direct and through tunnel.

Now I try:

workstation:$ docker pull localhost:5000/testapp:00.01Error response from daemon: Get http://localhost:5000/v2/: net/http: request canceled while waiting for connection (Client.Timeout exceeded while awaiting headers)workstation:> docker pull Dev2:5000/testapp:00.02Error response from daemon: Get http://Dev2:5000/v2/: net/http: request canceled while waiting for connection (Client.Timeout exceeded while awaiting headers)

The timeout is at least 30 seconds.Note: if I do the same thing from another Unix box running docker everything works right so this is particular to docker for Windows running on Windows 10. For some reason this fails.

I haven't been able to solve this. There are no HTTP proxies in the chain on either machine. It is on a local subnet. All other services on the server are accessible, etc. The "insecure-registries" in the Windows docker in the UI is set for both hosts and ports.

Is it a bug? In Windows 10 docker? It works fine from another Ubuntu box.