Here is some more troubleshooting information.  Also as a side note.  I am 
running an partner NFR self-support only version of AAP and have zero 
support from RedHat on this.  It also doesn't seem to matter if I run the 
job through command line ansible or through AAP.  The error is the same.  

My Group Vars

---
ansible_connection: winrm
ansible_winrm_server_cert_validation: ignore

Host Inventory

---
ansible_hostname: mikes-wintest.DOMAIN.CA

my WinRM settings after running the ConfigureAnsibleRemoting.ps1 script

PS C:\Users\ubermike\Desktop> winrm configSDDL default
Service
    RootSDDL = 
O:NSG:BAD:P(A;;GA;;;BA)(A;;GR;;;IU)(A;;GAGR;;;S-1-5-21-809043649-619790271-106372718-1977)S:P(AU;FA;GA;;;WD)(AU;SA;GXGW;;;WD)
    MaxConcurrentOperations = 4294967295
    MaxConcurrentOperationsPerUser = 1500
    EnumerationTimeoutms = 240000
    MaxConnections = 300
    MaxPacketRetrievalTimeSeconds = 120
    AllowUnencrypted = true
    Auth
        Basic = true
        Kerberos = true
        Negotiate = true
        Certificate = false
        CredSSP = true
        CbtHardeningLevel = Relaxed
    DefaultPorts
        HTTP = 5985
        HTTPS = 5986
    IPv4Filter = *
    IPv6Filter = *
    EnableCompatibilityHttpListener = false
    EnableCompatibilityHttpsListener = false
    CertificateThumbprint
    AllowRemoteAccess = true

My Ansible Host Kerb ticket

[uberm...@domain.ca@ansible ~]$ klist -c
Ticket cache: KCM:1944601976:978
Default principal: uberm...@domain.ca

Valid starting       Expires              Service principal
2022-06-12 08:10:56  2022-06-12 18:10:56  krbtgt/domain...@domain.ca
    renew until 2022-06-19 08:10:56

Latest Error Output from the job

{
  "unreachable": true,
  "msg": "kerberos: authGSSClientStep() failed: (('Unspecified GSS failure. 
 Minor code may provide more information', 851968), ('Server not found in 
Kerberos database', -1765328377)), ssl: 
HTTPSConnectionPool(host='inventory_hostname', port=5986): *Max retries 
exceeded with url: /wsman (Caused by 
NewConnectionError('<urllib3.connection.HTTPSConnection object at 
0x7f3ca1fd2430>: Failed to establish a new connection: [Errno -2] Name or 
service not known'))*",
  "changed": false
}


On Saturday, June 11, 2022 at 6:55:15 PM UTC-7 Michael Kennedy wrote:

> I am having a problem running WinRM connections with both basic and 
> kerberos auth.  
>
> My Ansible is deployed with RedHat AAP 4.2.0 on RHEL 9.  
>
> I setup a test Windows 2019 machine and ran the 
> ConfigureRemotingForAnsible.ps1 script against the host.  Rebooted the host 
> for good measure.  Tested from the Ansible server that I can telnet to 5985 
> and 5986 (confirmed) but I cannot run a Windows test playbook against the 
> host.
>
> Skipping callback 'oneline', as we already have a stdout callback.
> 18
> 19
> PLAYBOOK: test.yml 
> *************************************************************
> 20
> 2 plays in windows/test.yml
> 21
> 22
> PLAY [test raw module] 
> *********************************************************18:47:21
> 23
> 24
> TASK [Gathering Facts] 
> *********************************************************18:47:21
> 25
> *task path: /runner/project/windows/test.yml:2*
> 26
> *[WARNING]: The "winrm" connection plugin has an improperly configured 
> remote*
> 27
> *target value, forcing "inventory_hostname" templated value instead of the*
> 28
> *string*
> 29
> redirecting (type: modules) ansible.builtin.setup to ansible.windows.setup
> 30
> Using module file 
> /usr/share/ansible/collections/ansible_collections/ansible/windows/plugins/modules/setup.ps1
> 31
> Pipelining is enabled.
> 32
> <inventory_hostname> ESTABLISH WINRM CONNECTION FOR USER: administrator on 
> PORT 5986 TO inventory_hostname
> 33
> *fatal: [192.168.12.52]: UNREACHABLE! => {*
> 34
> * "changed": false,*
> 35
> * "msg": "ssl: HTTPSConnectionPool(host='inventory_hostname', port=5986): 
> Max retries exceeded with url: /wsman (Caused by 
> NewConnectionError('<urllib3.connection.HTTPSConnection object at 
> 0x7fa35f010f10>: Failed to establish a new connection: [Errno -2] Name or 
> service not known'))",*
> 36
> * "unreachable": true*
> 37
> *}*
>
> *Running a Windows test against a domain joined machine produces a 
> different error that I also cannot resolve.  *
>
> PLAY [Ping] 
> ********************************************************************18:53:19
> 3
> 4
> TASK [Gathering Facts] 
> *********************************************************18:53:19
> 5
> *[WARNING]: The "winrm" connection plugin has an improperly configured 
> remote*
> 6
> *target value, forcing "inventory_hostname" templated value instead of the*
> 7
> *string*
> 8
> *fatal: [srvrds04]: UNREACHABLE! => {"changed": false, "msg": "kerberos: 
> authGSSClientStep() failed: (('Unspecified GSS failure. Minor code may 
> provide more information', 851968), ('Server not found in Kerberos 
> database', -1765328377))", "unreachable": true}*
>
> *I am getting this error despite me confirming the SPN is fine. 
>  Confirming I can connect to the host with WinRM from a different domain 
> joined host.  Confirmed my Kerb ticket with kinit and list.  *
>
>
>

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