Ansible Windows Kerberos Authentification Bad HTTP response returned from server Code 500

Question

After configuring winRM on a windows server and filling all needed information to connect :

---
### winrm / win connection ###
ansible_winrm_realm: *My AD Domain*
ansible_connection: winrm
ansible_winrm_kerberos_delegation: yes
ansible_port: 5985
ansible_winrm_transport: kerberos

I got an

fatal: [MyServer]: UNREACHABLE! => {"changed": false, "msg": "kerberos: ('http', 'Bad HTTP response returned from server. Code 500')", "unreachable": true}

I have tried a lot of things including changing my configuration and checking if the WinRm is reachable and it was all good :

C:\Users\ME>winrs -r :http://myserver:5985/wsman -u:My_User -p:Password ipconfig

My WinRM Config :

PS C:\Users\XXXX> winrm get winrm/config/Service
Service
    MaxConcurrentOperations = 4294967295
    MaxConcurrentOperationsPerUser = 1500
    EnumerationTimeoutms = 240000
    MaxConnections = 300
    MaxPacketRetrievalTimeSeconds = 120
    AllowUnencrypted = false
    Auth
        Basic = false
        Kerberos = true
        Negotiate = true
        Certificate = false
        CredSSP = false
        CbtHardeningLevel = Relaxed
    DefaultPorts
        HTTP = 5985
        HTTPS = 5986
    IPv4Filter = *
    IPv6Filter = *
    EnableCompatibilityHttpListener = false
    EnableCompatibilityHttpsListener = false
    CertificateThumbprint
    AllowRemoteAccess = true


PS C:\Users\XXXX> winrm get winrm/config/Winrs
Winrs
    AllowRemoteShellAccess = true
    IdleTimeout = 7200000
    MaxConcurrentUsers = 2147483647
    MaxShellRunTime = 2147483647
    MaxProcessesPerShell = 2147483647
    MaxMemoryPerShellMB = 2147483647
    MaxShellsPerUser = 2147483647

Answer 1

Since i'm trying to use HTTP instead of HTTPS, the solution is to change the WinRm service config to allow encrypted connections by running the following command :

Set-Item -Path WSMan:\localhost\Service\AllowUnencrypted -Value true