Does this shed any light(?):

(ansible) MacBook-Pro:playbooks anthony$ ansible wrk04 -e 
@~/.ansible/secure.yml -m win_ping --ask-vault-pass
Vault password:
wrk04 | UNREACHABLE! => {
    "changed": false,
    "msg": "ntlm: requested auth method is ntlm, but requests_ntlm is not 
installed",
    "unreachable": true
}
(ansible) MacBook-Pro:playbooks anthony$ python -c "from requests_ntlm 
import requests_ntlm"
(ansible) MacBook-Pro:playbooks anthony$ echo $?
0
(ansible) MacBook-Pro:playbooks anthony$ python -c "import requests_ntlm"
(ansible) MacBook-Pro:playbooks anthony$ echo $?
0
(ansible) MacBook-Pro:playbooks anthony$ which python
/Users/anthony/ansible/bin/python
(ansible) MacBook-Pro:playbooks anthony$ ansible --version
ansible 2.5.0
  config file = /Users/anthony/.ansible.cfg
  configured module search path = 
[u'/Users/anthony/.ansible/plugins/modules', 
u'/usr/share/ansible/plugins/modules']
  ansible python module location = /Library/Python/2.7/site-packages/ansible
  executable location = /usr/local/bin/ansible
  python version = 2.7.10 (default, Oct  6 2017, 22:29:07) [GCC 4.2.1 
Compatible Apple LLVM 9.0.0 (clang-900.0.31)]

On Monday, May 14, 2018 at 4:46:50 PM UTC-4, Jordan Borean wrote:
>
> What about import requests_ntlm? If that works but Ansible doesn't it 
> sounds like Ansible is using a different Python interpreter to the one you 
> tested on.
>

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