Can't view interaction with private registry to troubleshoot

I would like to be able to see the detailed interactions with a docker v2 registry.

I'm using Artifactory to provide a docker v2 registry. It is configured to allow anonymous push and works on most of the computers in our office. About 1 in 3 computers (usually Macs) get an error

$ docker push stash.company.com:8443/pmd
The push refers to a repository [stash.company.com:8443/pmd]
24af4657da8d: Preparing
...
d17d48b2382a: Waiting
unauthorized: BAD_CREDENTIAL

I have been unable to figure out what is different between these computers that causes some computers to get this error and other to work as expected. I have compared ~/.docker/config.json to ensure there isn't a credential being passed.

What I have tried:

I tried adding --debug, -D to the docker push command, but it doesn't show any details about the interaction with the registry, so I can't see if it's trying to send a credential when it shouldn't be.

I also tried following the Docker daemon logs to see if they provided some details about the interaction with the registry, but it only shows a DNS lookup.

I have asked three or four times on the slack channel and I posted this question on SO:
https://stackoverflow.com/questions/45172693/docker-push-how-to-see-detailed-interaction-with-registry

It would seem that this isn't possible, so this is probably a feature request. I would like to be able to view detailed logs showing how my local docker is interacting with a registry.

Output of docker version:

$ docker version
Client:
 Version:      17.06.0-ce
 API version:  1.30
 Go version:   go1.8.3
 Git commit:   02c1d87
 Built:        Fri Jun 23 21:31:53 2017
 OS/Arch:      darwin/amd64

Server:
 Version:      17.06.0-ce
 API version:  1.30 (minimum version 1.12)
 Go version:   go1.8.3
 Git commit:   02c1d87
 Built:        Fri Jun 23 21:51:55 2017
 OS/Arch:      linux/amd64
 Experimental: true

Output of docker info:

$ docker info
Containers: 1
 Running: 0
 Paused: 0
 Stopped: 1
Images: 2
Server Version: 17.06.0-ce
Storage Driver: overlay2
 Backing Filesystem: extfs
 Supports d_type: true
 Native Overlay Diff: true
Logging Driver: json-file
Cgroup Driver: cgroupfs
Plugins:
 Volume: local
 Network: bridge host ipvlan macvlan null overlay
 Log: awslogs fluentd gcplogs gelf journald json-file logentries splunk syslog
Swarm: inactive
Runtimes: runc
Default Runtime: runc
Init Binary: docker-init
containerd version: cfb82a876ecc11b5ca0977d1733adbe58599088a
runc version: 2d41c047c83e09a6d61d464906feb2a2f3c52aa4
init version: 949e6fa
Security Options:
 seccomp
  Profile: default
Kernel Version: 4.9.36-moby
Operating System: Alpine Linux v3.5
OSType: linux
Architecture: x86_64
CPUs: 4
Total Memory: 1.952GiB
Name: moby
ID: RYYU:QDZ6:YNDV:7GSO:VEEV:YLXD:KPJW:RB4T:CIB6:AQKI:V6ET:ZF32
Docker Root Dir: /var/lib/docker
Debug Mode (client): false
Debug Mode (server): true
 File Descriptors: 18
 Goroutines: 30
 System Time: 2017-07-24T14:46:57.11149011Z
 EventsListeners: 1
No Proxy: *.local, 169.254/16
Registry: https://index.docker.io/v1/
Experimental: true
Insecure Registries:
 127.0.0.0/8
Live Restore Enabled: false

Additional environment details (AWS, VirtualBox, physical, etc.):
MacOS Sierra (10.12.5) with native install of Docker CE Stable

Start by reproducing the docker push against the private Artifactory Docker v2 registry described in the issue, with --debug or -D enabled, and compare the output with the daemon logs. The work is done when Docker CLI output exposes enough registry interaction detail to troubleshoot whether credentials are being sent.