Docker push to private registry freezes

Question

My scenario is that I have two VM's. One contains a docker registry, and the other one is my Minikube VM v0.34.1. When in my minikube vm, I try to push a docker image to the registry. docker push xxxx:5000/image . In turn I get this

1B0ff9cfff: Preparing
1B99b75fdb: Preparing
1B4cd8cf79: Preparing
1B53e365f3: Pushing  1.504MB/5.529MB

It freezes here then retries with the same result for several minutes (The exact amount uploaded varies slightly). I eventually will get this error:
HTTP/1.x transport connection broken: write tcp 10.0.2.15:44320->10.100.0.240:8080: write: connection reset by peer

I tried running it behind nginx with the exact same results. I started minikube with insecure-registry="xxxx:5000" I am getting activity on the docker registry side and it shows the repository at least being partially created.

So why might docker push be hanging and how can I prevent this partially completed docker push?

EDIT_1:

• What OS am i running? : My host OS is Windows 10, The virtual machine hosting my docker registry is Ubuntu 16.04.5 LTS

EDIT_2:

Docker logs from Minikube

Mar 04 21:07:11 minikube dockerd[2472]: time="2019-03-04T21:07:11.623859125Z" level=error msg="Upload failed, retrying: EOF"
Mar 04 21:07:11 minikube dockerd[2472]: time="2019-03-04T21:07:11.738542466Z" level=error msg="Upload failed, retrying: EOF"
Mar 04 21:07:11 minikube dockerd[2472]: time="2019-03-04T21:07:11.935610635Z" level=error msg="Upload failed, retrying: received unexpected HTTP status: 504 Connection Timed Out"
Mar 04 21:07:12 minikube dockerd[2472]: time="2019-03-04T21:07:12.620968642Z" level=error msg="Upload failed, retrying: EOF"
Mar 04 21:08:17 minikube dockerd[2472]: time="2019-03-04T21:08:17.876688403Z" level=error msg="Upload failed, retrying: received unexpected HTTP status: 504 Connection Timed Out"
Mar 04 21:08:17 minikube dockerd[2472]: time="2019-03-04T21:08:17.889263304Z" level=error msg="Upload failed, retrying: EOF"
Mar 04 21:08:18 minikube dockerd[2472]: time="2019-03-04T21:08:18.383804954Z" level=error msg="Upload failed, retrying: EOF"
Mar 04 21:08:18 minikube dockerd[2472]: time="2019-03-04T21:08:18.417687481Z" level=error msg="Upload failed, retrying: EOF"
Mar 04 21:08:39 minikube dockerd[2472]: time="2019-03-04T21:08:39.347357157Z" level=error msg="Upload failed, retrying: EOF"
Mar 04 21:08:39 minikube dockerd[2472]: time="2019-03-04T21:08:39.401567534Z" level=error msg="Upload failed, retrying: EOF"
Mar 04 21:08:39 minikube dockerd[2472]: time="2019-03-04T21:08:39.409308761Z" level=error msg="Upload failed, retrying: EOF"
Mar 04 21:08:39 minikube dockerd[2472]: time="2019-03-04T21:08:39.517508938Z" level=error msg="Upload failed, retrying: received unexpected HTTP status: 502 Server Hangup"
Mar 04 21:08:54 minikube dockerd[2472]: time="2019-03-04T21:08:54.664567971Z" level=error msg="Upload failed, retrying: received unexpected HTTP status: 502 Connection refused"
Mar 04 21:08:54 minikube dockerd[2472]: time="2019-03-04T21:08:54.709293521Z" level=error msg="Upload failed, retrying: received unexpected HTTP status: 502 Connection refused"
Mar 04 21:08:54 minikube dockerd[2472]: time="2019-03-04T21:08:54.716961617Z" level=error msg="Upload failed, retrying: received unexpected HTTP status: 502 Connection refused"
Mar 04 21:08:54 minikube dockerd[2472]: time="2019-03-04T21:08:54.824814356Z" level=error msg="Upload failed, retrying: received unexpected HTTP status: 502 Connection refused"
Mar 04 21:09:21 minikube dockerd[2472]: time="2019-03-04T21:09:21.047543662Z" level=error msg="Not continuing with push after error: context canceled"
Mar 04 21:09:29 minikube dockerd[2472]: time="2019-03-04T21:09:29.050147019Z" level=info msg="Attempting next endpoint for push after error: Get https://10.39.83.174:5000/v2/: Tunnel or SSL Forbidden"

Mar 04 21:11:16 minikube dockerd[2472]: time="2019-03-04T21:11:16.828676871Z" level=error msg="Upload failed, retrying: EOF"
Mar 04 21:11:17 minikube dockerd[2472]: time="2019-03-04T21:11:17.263497930Z" level=error msg="Upload failed, retrying: EOF"
Mar 04 21:11:17 minikube dockerd[2472]: time="2019-03-04T21:11:17.593178543Z" level=error msg="Upload failed, retrying: EOF"
Mar 04 21:11:17 minikube dockerd[2472]: time="2019-03-04T21:11:17.760548676Z" level=error msg="Upload failed, retrying: received unexpected HTTP status: 504 Connection Timed Out"

Answer 1

Posting @Zannith comment as an answer:

Check if NO_PROXY entry have been configured to the VM where the registry is currently running...