So, after some further testing, I am able to push a small image based on windows-server-nano to my repository. But when I try to push a larger image I get "unauthorized: authentication required" after a while. Some layers succeed in pushing, but when I get to a larger layer it seems to stall.
PS C:\Program Files> docker push servername/registryname/imagename:tagname
The push refers to repository [servername/registryname/imagename]
73db119f1423: Pushed
39017a61fb52: Pushed
246da8a4d4c9: Pushed
a114056875fb: Pushed
9f99dd0b742e: Pushed
495c9abcf140: Pushed
63dc895b2a27: Pushed
d3dc3d141977: Pushed
5b7901df17bd: Pushed
3e1a4631d6cf: Pushing [==================================================>] 13.15GB/13.15GB
7526e29ba0ea: Pushed
b3bc068f2de5: Pushed
1fd88f70cb45: Pushed
1c5d24ff49f1: Pushed
bfd396c19d59: Pushing [==================================================>] 1.081GB
aa6445a500cd: Pushing [==================================================>] 890.4MB
cb4a90dd60da: Skipped foreign layer
bf16baf8d810: Skipped foreign layer
unauthorized: authentication required
Worth noting also, that if I subsequently try to push a smaller image again (without performing "docker login"), the push succeeds.
Any idea why that might be?
Best,