Unable to configure WinRm https listener
I've made recently HTTPS + WINRM and got exactly the same problems.
The solution is - before invoking command
winrm quickconfig -transport:https
you must do some prerequisite job. to be more specific you must install on the server certificate.
you can look how to do that here - http://blogs.technet.com/b/jhoward/archive/2005/02/02/365323.aspx
to make the long story short:
1 create CA ROOT certificate
cmd> makecert -pe -n "CN=Test And Dev Root Authority" -ss my -sr LocalMachine -a sha1 -sky signature -r "Test And Dev Root Authority.cer"
export it with private key from certificates mmc from host where you invoke makecert and install on the server and client host to certificates.mmc -local machine - Trusted root authorities
2 create ssl certificate
cmd> makecert -pe -n "CN=8.8.8.8" -ss my -sr LocalMachine -a sha1 -sky exchange -eku 1.3.6.1.5.5.7.3.1 -in "Test And Dev Root Authority" -is MY -ir LocalMachine -sp "Microsoft RSA SChannel Cryptographic Provider" -sy 12 8.8.8.8.cer
where CN=8.8.8.8 - must be IP of the server
export the certificate with private key from certificate mmc and import to the server to certificates.mmc - localmachine - personal
ONLY AFTER THAT invoke
winrm quickconfig -transport:https
i hope my spent a coiuple of days trying to figure out how it works will save your couple of days