cd "c:\program files (x86)\iis express"
IisExpressAdminCmd.exe setupsslUrl -url:https://locahost:20000 -UseSelfSigned
Using netsh http commands (Run as Administrator):
netsh http add sslcert ipport=0.0.0.0:10000 certhash=846b7ea62c4bf18a86a9e7bb5fc7d62025ba7e73 appid={2b98ce84-190a-411e-b941-2c047b7cc895}
appid is a guid. Use Guid.NewGuid() to generate one in C#. or [guid]::NewGuid() from Powershell
certhash is the hash obtained from the existing SSL cert that has been applied to ports 44300 - 44399. You can get details of the cert by running
netsh http show sslcert