Ansible Errors & Solutions with Windows Server

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PS C:\Users\rajesh> (New-Object -TypeName System.Net.WebClient).DownloadFile($url, $file)
Exception calling "DownloadFile" with "2" argument(s): "The request was aborted: Could not create SSL/TLS secure
channel."
At line:1 char:1
+ (New-Object -TypeName System.Net.WebClient).DownloadFile($url, $file)
+ ~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~
    + CategoryInfo          : NotSpecified: (:) [], MethodInvocationException
    + FullyQualifiedErrorId : WebException

PS C:\Users\rajesh> [Net.ServicePointManager]::SecurityProtocol = [Net.SecurityProtocolType]::Tls12
PS C:\Users\rajesh> (New-Object -TypeName System.Net.WebClient).DownloadFile($url, $file)
PS C:\Users\rajesh>

[Net.ServicePointManager]::SecurityProtocol = [Net.SecurityProtocolType]::Tls12

[root@master files]# sudo pip install markupsafe
Traceback (most recent call last):
  File "/bin/pip", line 9, in <module>
    load_entry_point('pip==21.1.2', 'console_scripts', 'pip')()
  File "/usr/lib/python2.7/site-packages/pkg_resources.py", line 378, in load_entry_point
    return get_distribution(dist).load_entry_point(group, name)
  File "/usr/lib/python2.7/site-packages/pkg_resources.py", line 2566, in load_entry_point
    return ep.load()
  File "/usr/lib/python2.7/site-packages/pkg_resources.py", line 2260, in load
    entry = __import__(self.module_name, globals(),globals(), ['__name__'])
  File "/usr/lib/python2.7/site-packages/pip/__init__.py", line 1, in <module>
    from typing import List, Optional
ImportError: No module named typing
[root@master files]# sudo pip install xmltodict
Traceback (most recent call last):
  File "/bin/pip", line 9, in <module>
    load_entry_point('pip==21.1.2', 'console_scripts', 'pip')()
  File "/usr/lib/python2.7/site-packages/pkg_resources.py", line 378, in load_entry_point
    return get_distribution(dist).load_entry_point(group, name)
  File "/usr/lib/python2.7/site-packages/pkg_resources.py", line 2566, in load_entry_point
    return ep.load()
  File "/usr/lib/python2.7/site-packages/pkg_resources.py", line 2260, in load
    entry = __import__(self.module_name, globals(),globals(), ['__name__'])
  File "/usr/lib/python2.7/site-packages/pip/__init__.py", line 1, in <module>
    from typing import List, Optional
ImportError: No module named typing

[root@master ~]# ansible --version
/usr/lib/python2.7/site-packages/ansible/parsing/vault/__init__.py:44: CryptographyDeprecationWarning: Python 2 is no longer supported by the Python core team. Support for it is now deprecated in cryptography, and will be removed in the next release.
  from cryptography.exceptions import InvalidSignature

Solution - https://stackoverflow.com/questions/67278017/pip-command-line-importerror-no-module-named-typing

[root@master ~]# ansible all -i 20.81.234.228, -m win_ping
/usr/lib/python2.7/site-packages/ansible/parsing/vault/__init__.py:44: CryptographyDeprecationWarning: Python 2 is no longer supported by the Python core team. Support for it is now deprecated in cryptography, and will be removed in the next release.
  from cryptography.exceptions import InvalidSignature
20.81.234.228 | UNREACHABLE! => {
    "changed": false,
    "msg": "Failed to connect to the host via ssh: ssh: connect to host 20.81.234.228 port 22: Connection timed out",
    "unreachable": true
}
[root@master ~]#


[root@master ~]# ansible all -i 20.81.234.228, -m win_ping
/usr/lib/python2.7/site-packages/ansible/parsing/vault/__init__.py:44: CryptographyDeprecationWarning: Python 2 is no longer supported by the Python core team. Support for it is now deprecated in cryptography, and will be removed in the next release.
  from cryptography.exceptions import InvalidSignature
20.81.234.228 | UNREACHABLE! => {
    "changed": false,
    "msg": "Failed to connect to the host via ssh: ssh: connect to host 20.81.234.228 port 22: Connection timed out",
    "unreachable": true
}

[root@master ~]# ansible all -i 20.81.234.228, -m win_ping -c winrm -u rajesh
/usr/lib/python2.7/site-packages/ansible/parsing/vault/__init__.py:44: CryptographyDeprecationWarning: Python 2 is no longer supported by the Python core team. Support for it is now deprecated in cryptography, and will be removed in the next release.
  from cryptography.exceptions import InvalidSignature
20.81.234.228 | UNREACHABLE! => {
    "changed": false,
    "msg": "ssl: auth method ssl requires a password",
    "unreachable": true
}

[root@master ~]# ansible all -i 20.81.234.228, -m win_ping -c winrm -u rajesh -e 'ansible_password=Ghs6834&dhks'
/usr/lib/python2.7/site-packages/ansible/parsing/vault/__init__.py:44: CryptographyDeprecationWarning: Python 2 is no longer supported by the Python core team. Support for it is now deprecated in cryptography, and will be removed in the next release.
  from cryptography.exceptions import InvalidSignature
20.81.234.228 | UNREACHABLE! => {
    "changed": false,
    "msg": "ssl: HTTPSConnectionPool(host='20.81.234.228', port=5986): Max retries exceeded with url: /wsman (Caused by SSLError(SSLError(1, u'[SSL: CERTIFICATE_VERIFY_FAILED] certificate verify failed (_ssl.c:618)'),))",
    "unreachable": true
}

[root@master ~]# ansible all -i 20.81.234.228, -m win_ping -c winrm -u rajesh -e 'ansible_password=Ghs6834&dhks ansible_port=5985'
/usr/lib/python2.7/site-packages/ansible/parsing/vault/__init__.py:44: CryptographyDeprecationWarning: Python 2 is no longer supported by the Python core team. Support for it is now deprecated in cryptography, and will be removed in the next release.
  from cryptography.exceptions import InvalidSignature
20.81.234.228 | UNREACHABLE! => {
    "changed": false,
    "msg": "plaintext: the specified credentials were rejected by the server",
    "unreachable": true
}

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