Openshift: Error pulling image from remote, secure docker registry using certificates - openshift

Question

I use the all-in-one VM of Openshift origin.
I am trying to pull images from a private, secure registry using an Image Stream. This is the ImageStream definition:
apiVersion: v1
kind: ImageStream
metadata:
name: my-image-stream
annotations:
description: Keeps track of changes in the application image
name: my-image
spec:
dockerImageRepository: "my.registry.net/myproject/my-image"
The repository is secured with a certificate. On my local machine, i have them in /etc/docker/certs.d/my.registry.net and I can login with docker login my.registry.net.
When I run oc import-image, however, I get the following error:
The import completed with errors.
Name: my-image
Namespace: myproject
Created: About an hour ago
Labels: <none>
Description: Keeps track of changes in the application image
Annotations: openshift.io/image.dockerRepositoryCheck=2017-01-27T08:09:49Z
Docker Pull Spec: 172.30.53.244:5000/myproject/my-image
Unique Images: 0
Tags: 1
latest
tagged from my.registry.net/myproject/my-image
! error: Import failed (InternalError): Internal error occurred: Get https://my.registry.net/v2/: remote error: handshake failure
About an hour ago
I have copied the certificates to the vagrant machine and restarted the docker daemon, but the problem remains. I have not found any documentation on how to properly add the certificates, so I just put them in the usual docker folder.
What is the appropriate way to make this work?
Update in response to rezie's answer:
There is no file etc/origin/master/ca-bundle.crt on my vagrant box. I found the following ca-bundle.crt files :
$ find / -iname ca-bundle.crt
/etc/pki/tls/certs/ca-bundle.crt
##multiple lines like
/var/lib/docker/devicemapper/mnt/something-hash-like/rootfs/etc/pki/tls/certs/ca-bundle.crt
/var/lib/origin/openshift.local.config/master/ca-bundle.crt
I appended the root certificate to /etc/pki/tls/certs/ca-bundle.crt and to var/lib/origin/openshift.local.config/master/ca-bundle.crt, but that did not change anything.
Please note, however, that I do not need to have this root certificate in /etc/docker/certs.d/... in order to login directly using docker login my.registry.net
I have appended

Answer 1

I cannot comment due tow lo karma so I'll write an answer saying almost the same as rezie.
The error:
! error: Import failed (InternalError): Internal error occurred: Get https://my.registry.net/v2/: remote error: handshake failure
About an hour ago
Comes from OpenShift, not from docker, therefore adding it to /etc/docker/certs.d/my.registry.net doesn't prevent the error from happening.
You should add the CA certificate at OS level, my guess is the steps failed for some reason so do it this way:
openssl s_client -connect my.registry.net:443 </dev/null |
sed -ne '/-BEGIN CERTIFICATE-/,/-END CERTIFICATE-/p' \
> /etc/pki/ca-trust/source/anchors/my.registry.net.crt &&
update-ca-trust check && update-ca-trust extract
Finally test if it worked running
curl https://my.registry.net/v2
If it doesn't give you a certificate error and you still can't do the oc import restart the atomic-openshift-master-api service

Answer 2

Try appending your CA (the same one you said you said that was used in the my.registry.net directory) into Openshift's ca bundle (e.g. /etc/origin/master/ca-bundle.crt. Then restart the service and reattempt import-image (making sure that you do not include the --insecure flag).
For reference, check out this issue from the Origin project. As you've mentioned, there's currently no way to supply certificates along with the dockercfg secret, and the suggestion from that issue is to add the CA as a trusted root CA across all the hosts.