I'm having trouble authenticating over AD to windows machines from my ansible host. 'Server not found in Kerberos Database' on Ubuntu 16.10

Question

I'm having trouble authenticating over AD to windows machines from my ansible host. I have a valid kerberos ticket -

klist
Credentials cache: FILE:/tmp/krb5cc_1000
        Principal: [email protected]

  Issued                Expires               Principal
Mar 10 09:15:27 2017  Mar 10 19:15:24 2017  krbtgt/[email protected]

My kerberos config looks fine to me -

cat /etc/krb5.conf
[libdefaults]
        default_realm = SOMEDOMAIN.LOCAL
#       dns_lookup_realm = true
#       dns_lookup_kdc = true
#       ticket_lifetime = 24h
#       renew_lifetime = 7d
#       forwardable = true

# The following krb5.conf variables are only for MIT Kerberos.
#       kdc_timesync = 1
#       forwardable = true
#       proxiable = true

# The following encryption type specification will be used by MIT Kerberos
# if uncommented.  In general, the defaults in the MIT Kerberos code are
# correct and overriding these specifications only serves to disable new
# encryption types as they are added, creating interoperability problems.
#
# Thie only time when you might need to uncomment these lines and change
# the enctypes is if you have local software that will break on ticket
# caches containing ticket encryption types it doesn't know about (such as
# old versions of Sun Java).

#       default_tgs_enctypes = des3-hmac-sha1
#       default_tkt_enctypes = des3-hmac-sha1
#       permitted_enctypes = des3-hmac-sha1

# The following libdefaults parameters are only for Heimdal Kerberos.
#       v4_instance_resolve = false
#       v4_name_convert = {
#               host = {
#                       rcmd = host
#                       ftp = ftp
#               }
#               plain = {
#                       something = something-else
#               }
#       }
#       fcc-mit-ticketflags = true

[realms]
        SOMEDOMAIN.LOCAL = {
                kdc = prosperitydc1.somedomain.local
                kdc = prosperitydc2.somedomain.local
                default_domain = somedomain.local
                admin_server = somedomain.local
        }
[domain_realm]
        .somedomain.local = SOMEDOMAIN.LOCAL
        somedomain.local = SOMEDOMAIN.LOCAL

When running a test command - ansible windows -m win_ping -vvvvv I get

'Server not found in Kerberos database'.
     ansible windows -m win_ping -vvvvv
    Using /etc/ansible/ansible.cfg as config file
    Loading callback plugin minimal of type stdout, v2.0 from /usr/lib/python2.7/dist-packages/ansible/plugins/callback/__init__.pyc
    Using module file /usr/lib/python2.7/dist-packages/ansible/modules/core/windows/win_ping.ps1
    <kerberostest.somedomain.local> ESTABLISH WINRM CONNECTION FOR USER: [email protected] on PORT 5986 TO kerberostest.somedomain.local
    <kerberostest.somedomain.local> WINRM CONNECT: transport=kerberos endpoint=https://kerberostest.somedomain.local:5986/wsman
    <kerberostest.somedomain.local> WINRM CONNECTION ERROR: authGSSClientStep() failed: (('Unspecified GSS failure.  Minor code may provide more information', 851968), ('Server not found in Kerberos database', -1765328377))
    Traceback (most recent call last):
      File "/usr/lib/python2.7/dist-packages/ansible/plugins/connection/winrm.py", line 154, in _winrm_connect
        self.shell_id = protocol.open_shell(codepage=65001)  # UTF-8
      File "/home/prosperity/.local/lib/python2.7/site-packages/winrm/protocol.py", line 132, in open_shell
        res = self.send_message(xmltodict.unparse(req))
      File "/home/prosperity/.local/lib/python2.7/site-packages/winrm/protocol.py", line 207, in send_message
        return self.transport.send_message(message)
      File "/home/prosperity/.local/lib/python2.7/site-packages/winrm/transport.py", line 181, in send_message
        prepared_request = self.session.prepare_request(request)
      File "/home/prosperity/.local/lib/python2.7/site-packages/requests/sessions.py", line 407, in prepare_request
        hooks=merge_hooks(request.hooks, self.hooks),
      File "/home/prosperity/.local/lib/python2.7/site-packages/requests/models.py", line 306, in prepare
        self.prepare_auth(auth, url)
      File "/home/prosperity/.local/lib/python2.7/site-packages/requests/models.py", line 543, in prepare_auth
        r = auth(self)
      File "/home/prosperity/.local/lib/python2.7/site-packages/requests_kerberos/kerberos_.py", line 308, in __call__
        auth_header = self.generate_request_header(None, host, is_preemptive=True)
      File "/home/prosperity/.local/lib/python2.7/site-packages/requests_kerberos/kerberos_.py", line 148, in generate_request_header
        raise KerberosExchangeError("%s failed: %s" % (kerb_stage, str(error.args)))
    KerberosExchangeError: authGSSClientStep() failed: (('Unspecified GSS failure.  Minor code may provide more information', 851968), ('Server not found in Kerberos database', -1765328377))

    kerberostest.somedomain.local | 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 able to ssh to the target machine

 ssh -v1 kerberostest.somedomain.local -p 5986
OpenSSH_7.3p1 Ubuntu-1, OpenSSL 1.0.2g  1 Mar 2016
debug1: Reading configuration data /etc/ssh/ssh_config
debug1: /etc/ssh/ssh_config line 19: Applying options for *
debug1: Connecting to kerberostest.somedomain.local [10.10.20.84] port 5986.
debug1: Connection established.

I can also ping all hosts with their hostname. I'm at a loss :(

Here is the ansible host file-

sudo cat /etc/ansible/hosts               
# This is the default ansible 'hosts' file.
#
# It should live in /etc/ansible/hosts
#
#   - Comments begin with the '#' character
#   - Blank lines are ignored
#   - Groups of hosts are delimited by [header] elements
#   - You can enter hostnames or ip addresses
#   - A hostname/ip can be a member of multiple groups

# Ex 1: Ungrouped hosts, specify before any group headers.

## green.example.com
## blue.example.com
## 192.168.100.1
## 192.168.100.10

# Ex 2: A collection of hosts belonging to the 'webservers' group

## [webservers]
## alpha.example.org
## beta.example.org
## 192.168.1.100
## 192.168.1.110

# If you have multiple hosts following a pattern you can specify
# them like this:

## www[001:006].example.com

# Ex 3: A collection of database servers in the 'dbservers' group

## [dbservers]
## 
## db01.intranet.mydomain.net
## db02.intranet.mydomain.net
## 10.25.1.56
## 10.25.1.57

# Here's another example of host ranges, this time there are no
# leading 0s:

## db-[99:101]-node.example.com
[monitoring-servers]
#nagios
10.10.20.75 ansible_connection=ssh ansible_user=nagios

[windows]
#fileserver.somedomain.local#this machine isnt joined to the domain yet.
kerberostest.SOMEDOMAIN.LOCAL


[windows:vars]
#the following works for windows local account authentication
#ansible_ssh_user = prosperity
#ansible_ssh_pass = *********
#ansible_connection = winrm
#ansible_ssh_port = 5986
#ansible_winrm_server_cert_validation = ignore

#vars needed to authenticate on the windows domain using kerberos
ansible_user = [email protected]
ansible_connection = winrm
ansible_winrm_scheme = https
ansible_winrm_transport = kerberos
ansible_winrm_server_cert_validation = ignore

I also tried connecting to the domain with realmd with success, but running the ansible command produced the same result.

Answer 1

This looks like a case of a missing SPN.

Here's the relevant error snippet:

<kerberostest.prosperityerp.local> ESTABLISH WINRM CONNECTION FOR USER: [email protected] on PORT 5986 TO kerberostest.prosperityerp.local
    <kerberostest.prosperityerp.local> WINRM CONNECT: transport=kerberos endpoint=https://kerberostest.prosperityerp.local:5986/wsman
    <kerberostest.prosperityerp.local> WINRM CONNECTION ERROR: authGSSClientStep() failed: (('Unspecified GSS failure.  Minor code may provide more information', 851968), ('Server not found in Kerberos database', -1765328377))

And that is based off something I noticed in your Ansible configuration file:

[windows]
#fileserver.prosperityerp.local#this machine isnt joined to the domain yet.
kerberostest.PROSPERITYERP.LOCAL

I think the this machine isnt joined to the domain yet line in that file is a good indicator that the SPN HTTP/kerberostest.prosperityerp.local does not exist in Active Directory which would be causing the "server not found" message. You can SSH to kerberostest.prosperityerp.local, probably because it exists in DNS or in a Hosts file of the client machine, but unless and until the SPN HTTP/kerberostest.prosperityerp.local is created in Active Directory you will continue to get that error message. Adding that SPN properly in at this point would be a whole other topic of discussion.

1. You could use a command like this to test if you have that SPN defined:

   setspn -Q HTTP/kerberostest.prosperityerp.local

SPNs exists to represent to a Kerberos client where to find the service instance for that service on the network.

2. Also run:

nslookup kerberostest.prosperityerp.local

on at least two client machines to make sure the FQDN of the IP host where the Kerberized is running exists DNS. DNS is a requirement for Kerberos to properly run in a network.

3. Finally, you could use Wireshark on the client for further analysis, use the filter kerberos to highlight only kerberos traffic.