Due to time crunch and that this is just for testing and my own 
edification, I enabled basic auth and it's working now.  I want to 
understand better why I wasn't able to leave basic off and rely on the 
certification.

On Tuesday, September 13, 2022 at 3:05:49 PM UTC-5 Paul Briery wrote:

> I'm trying to understand Ansible better in order to use it in my company's 
> production environment.  In order to test and understand I've setup 2 VM's 
> with server 2019 and am using a Windows 2010 system with WSL enabled and 
> Ubuntu 22.04.  There is no domain setup in this configuration and I don't 
> want to set one up.  I do not want to use basic transport so I have created 
> a cert to use.  Basically, I've followed these steps 
> <https://adamtheautomator.com/winrm-for-ansible/> and had success 
> before.  A week ago I decided that I was going to try retracing my steps 
> and see if I could duplicate the results again.  Sadly I have had no such 
> luck.  I get the following error when I try running a straight-up ansible 
> command or using a playbook:
> 192.168.4.70 | UNREACHABLE! => {
>     "changed": false,
>     "msg": "ssl: the specified credentials were rejected by the server",
>     "unreachable": true
> }
> Obviously, I'm missing something that I had not before and I'm at my wit's 
> end.  The fixes I've seen posted are to use ntlm/Kerberos or enable basic.  
> I'm not wanting to do either of these.  I'm not sure about my cert.  In 
> this article 
> <https://docs.microsoft.com/en-us/troubleshoot/windows-client/system-management-components/configure-winrm-for-https>
>  it 
> states "If you have more than one local computer account server certificate 
> installed, confirm the Certificate Thumbprint displayed by Winrm enumerate 
> winrm/config/listener is the same Thumbprint on the *Details* tab of the 
> certificate.".  In the steps I followed I have 2 thumb prints 1 for the 
> server and 1 from the ansible host.
>
>
>
> $serverCert
> Thumbprint                                Subject                         
>                                                            
> ----------                                -------                         
>                                                            
> 65F93B914048C98A567C71B1F7831F9873C283DB  CN=WIN-C3EQOG6836M   
>
> $ansibleCert
> Thumbprint                                Subject                         
>                                                            
> ----------                                -------                         
>                                                            
> 65D2499EB375E0B7064596D20AB096E21A184C69  CN=ansible   
>
> From details tab in Cert MMC
> Trusted Root Certification Authorities/ansible & Trusted People
> 65d2499eb375e0b7064596d20ab096e21a184c69
>
> PS C:\Users\Administrator> Winrm enumerate winrm/config/listener
> Listener
>     Address = *
>     Transport = HTTP
>     Port = 5985
>     Hostname
>     Enabled = true
>     URLPrefix = wsman
>     CertificateThumbprint
>     ListeningOn = 127.0.0.1, 192.168.4.70, ::1, 
> fd5e:d04:f269:1:6014:e42c:ba33:80ab, fe80::6014:e42c:ba33:80ab%6
>
> Listener
>     Address = *
>     Transport = HTTPS
>     Port = 5986
>     Hostname = WIN-C3EQOG6836M
>     Enabled = true
>     URLPrefix = wsman
>     CertificateThumbprint = 65F93B914048C98A567C71B1F7831F9873C283DB
>     ListeningOn = 127.0.0.1, 192.168.4.70, ::1, 
> fd5e:d04:f269:1:6014:e42c:ba33:80ab, fe80::6014:e42c:ba33:80ab%6
>
> Should the thumbprint be the cert for the server or for the ansible user?
>
> Here is my winrm/config:
> Config
>     MaxEnvelopeSizekb = 500
>     MaxTimeoutms = 60000
>     MaxBatchItems = 32000
>     MaxProviderRequests = 4294967295
>     Client
>         NetworkDelayms = 5000
>         URLPrefix = wsman
>         AllowUnencrypted = false
>         Auth
>             Basic = true
>             Digest = true
>             Kerberos = true
>             Negotiate = true
>             Certificate = true
>             CredSSP = false
>         DefaultPorts
>             HTTP = 5985
>             HTTPS = 5986
>         TrustedHosts
>     Service
>         RootSDDL = 
> O:NSG:BAD:P(A;;GA;;;BA)(A;;GR;;;IU)S:P(AU;FA;GA;;;WD)(AU;SA;GXGW;;;WD)
>         MaxConcurrentOperations = 4294967295
>         MaxConcurrentOperationsPerUser = 1500
>         EnumerationTimeoutms = 240000
>         MaxConnections = 300
>         MaxPacketRetrievalTimeSeconds = 120
>         AllowUnencrypted = false
>         Auth
>             Basic = false
>             Kerberos = true
>             Negotiate = true
>             Certificate = true
>             CredSSP = false
>             CbtHardeningLevel = Relaxed
>         DefaultPorts
>             HTTP = 5985
>             HTTPS = 5986
>         IPv4Filter = *
>         IPv6Filter = *
>         EnableCompatibilityHttpListener = false
>         EnableCompatibilityHttpsListener = false
>         CertificateThumbprint
>         AllowRemoteAccess = true
>     Winrs
>         AllowRemoteShellAccess = true
>         IdleTimeout = 7200000
>         MaxConcurrentUsers = 2147483647 <(214)%20748-3647>
>         MaxShellRunTime = 2147483647 <(214)%20748-3647>
>         MaxProcessesPerShell = 2147483647 <(214)%20748-3647>
>         MaxMemoryPerShellMB = 2147483647 <(214)%20748-3647>
>         MaxShellsPerUser = 2147483647 <(214)%20748-3647>
>
> Also my ansible Inventory file:
> [windows]
> 192.168.4.70
> 192.168.4.71
>
> [windows:vars]
>  ansible_user=ansible
>  ansible_password=Password1!
>  ansible_connection=winrm
>  ansible_winrm_server_cert_validation=ignore
>  ansible_port=5986
>
>
>
>
>
>

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