Error net/http: request canceled while waiting for connection (Client.Timeout exceeded while awaiting headers)

Recently upgraded to the Docker version gitlab-ee:15.6.8-ee.0, at the same time enabled the self-hosted Container Registry.

I can successfully login in with docker login (ignore the insecure CLI)

$ docker login gitlab.<snip>.real-time.com -u me -p gxxxx-xxxxxxxxxxxxxxxxx
WARNING! Using --password via the CLI is insecure. Use --password-stdin.
Login Succeeded

I can successfully build the image.
I see the image and tag with docker image ls but a docker push fails.

$ docker push gitlab.<snip>.real-time.com:5050/test-group/www.test.com
Using default tag: latest
The push refers to repository [gitlab.<snip>.real-time.com:5050/test-group/www.test.com]
Get "https://gitlab.<snip>.real-time.com:5050/v2/": net/http: request canceled while waiting for connection (Client.Timeout exceeded while awaiting headers)

I’d assume if my access token was invalid the docker login would fail.

Troubleshooting I’ve given my access token full rights.

  • api, read_api, read_user, read_repository, write_repository, read_registry, write_registry

My development platform is macOS and Docker Desktop

sw_vers
ProductName:	macOS
ProductVersion:	12.6.3
BuildVersion:	21G419
docker --version
Docker version 20.10.23, build 7155243

Docker run command

docker run --detach \
  --hostname gitlab.<snip>.real-time.com \
  --publish 443:443 --publish 80:80 --publish 22:22 --publish 5050:5050 \
  --name gitlab \
  --restart always \
  --volume $GITLAB_HOME/config:/etc/gitlab \
  --volume $GITLAB_HOME/logs:/var/log/gitlab \
  --volume $GITLAB_HOME/data:/var/opt/gitlab \
  --shm-size 256m \
  --log-opt max-size=1024m \
    gitlab/gitlab-ee:15.6.8-ee.0

I have my gitlab SSL certificate and key in the macOS KeyChain.

Found other links that recommend putting the .cert and .key into .docker/certs.d/gitlab.<snip>.real-time.com:5050/ and restarted Docker Desktop. I have this setup.

I’m not sure what logs would be helpful. Let me know.

Any assistance would be appreciate.

Thanks.