Currently I did a workaround however ideally this shouldn't be needed.
Created the following script:

forward.sh

#!/bin/sh

socat tcp-listen:5000,reuseaddr,fork tcp:192.168.0.38:5000 &

This allows to have the remote host port on localhost, this way it doesn't complain about https.
Added the following entry to the waypoint template file.

hook {
      when    = "before"
      command = ["sh", "forward.sh"]
}

Hey @marcotuna ! Thanks for opening an issue on Waypoint!

Do you have anything in your daemon settings file? Mine is at /etc/docker/daemon.json. On my system, I had to setup docker to allow for pushing to insecure registries:

• https://docs.docker.com/registry/insecure/#deploy-a-plain-http-registry

{
  "insecure-registries" : ["myregistrydomain.com:5000"]
}

That's interesting that it works with localhost, likely a bug on our end if that works but the IP address does not. We'll leave this issue open to track it!

Hello Guys, hitting the same issue with v0.8.2 even following your recommendation @briancain. In my case, I'm using the FQDN instead of localhost or IP and this is the error I'm getting:

Image built: waypoint.local/orcha-client:latest (amd64)
 + Running push build v11
 + Tagging Docker image: waypoint.local/orcha-client:latest => registry.service.dc1.consul:5000/orcha-client:latest
 ! Pushing Docker image...
 │ The push refers to repository [registry.service.dc1.consul:5000/orcha-client]
! unable to stream Docker logs to terminal: Get
  "https://registry.service.dc1.consul:5000/v2/": http: server gave HTTP response
  to HTTPS client

Registry block configs:

registry {
       use "docker" {
         image = "registry.service.dc1.consul:5000/orcha-client"
         tag   = "latest"
         local = false
         insecure = true
       }
     }

This is still very reproducible on 0.10.0. I experienced this with ODR running on Kubernetes and Git remote runners.

registry {
  use "docker" {
    image = "docker-registry:5000/busybox"
    tag = "latest"
    insecure = true
  }
}

The result is similar to @wallacepf:

❌ Building Docker image with kaniko...
! unable to negotiate with upstream: Get "https://docker-registry:5000/v2/": http:
  server gave HTTP response to HTTPS client

As a guess: I think the ai.Insecure value is not being set when passing around instructions with gRPC.

@arbourd are you using the docker-pull builder plugin, or the docker builder plugin here?

Great question @paladin-devops. I moved on from this solution and never committed it but I have a feeling I tried both? I think I started with docker-pull (pulling busybox and shipping it to the local reg to satisfy the ODR stuff for empty builds).