$ ansible --version

ansible 2.9.13

  config file = /Users/user/.ansible.cfg

  configured module search path = ['/Users/user/.ansible/plugins/modules', 
'/usr/share/ansible/plugins/modules']

  ansible python module location = 
/Library/Frameworks/Python.framework/Versions/3.8/lib/python3.8/site-packages/ansible

  executable location = 
/Library/Frameworks/Python.framework/Versions/3.8/bin/ansible

  python version = 3.8.5 (v3.8.5:580fbb018f, Jul 20 2020, 12:11:27) [Clang 
6.0 (clang-600.0.57)]

I have the following task

# Mail the files

- *name*: Mail the zip file

  *mail*:

    *host*: smtp.gmail.com

    *port*: 465 # 587 fails as well

    *secure*: starttls  # always fails as well

    *charset*: utf-8

    *username*: "{{ user }}"

    *password*: "{{ pw }}"

    *to*: "[email protected]"

    *from*: "[email protected]"

    *subject*: "Private key and CSR files"

    *attach*: "{{ archive_file }}"

    *body*: "Ansible-generated private and CSR files for {{ common_name }}"

  *delegate_to*: localhost


I'm very sure I'm passing the correct username and password. However I get 
this error when I run my playbook.


<localhost> ESTABLISH LOCAL CONNECTION FOR USER: user

<localhost> EXEC /bin/sh -c 'echo ~user && sleep 0'

<localhost> EXEC /bin/sh -c '( umask 77 && mkdir -p "` echo 
/Users/user/.ansible/tmp `"&& mkdir "` echo 
/Users/user/.ansible/tmp/ansible-tmp-1599411608.7587368-75656-16246975542505 
`" && echo ansible-tmp-1599411608.7587368-75656-16246975542505="` echo 
/Users/user/.ansible/tmp/ansible-tmp-1599411608.7587368-75656-16246975542505 
`" ) && sleep 0'

Using module file 
/Library/Frameworks/Python.framework/Versions/3.8/lib/python3.8/site-packages/ansible/modules/notification/mail.py

<localhost> PUT 
/Users/user/.ansible/tmp/ansible-local-75569bryuh8_h/tmp3plwd3_u TO 
/Users/user/.ansible/tmp/ansible-tmp-1599411608.7587368-75656-16246975542505/AnsiballZ_mail.py

<localhost> EXEC /bin/sh -c 'chmod u+x 
/Users/user/.ansible/tmp/ansible-tmp-1599411608.7587368-75656-16246975542505/ 
/Users/user/.ansible/tmp/ansible-tmp-1599411608.7587368-75656-16246975542505/AnsiballZ_mail.py
 
&& sleep 0'

<localhost> EXEC /bin/sh -c '/usr/bin/python 
/Users/user/.ansible/tmp/ansible-tmp-1599411608.7587368-75656-16246975542505/AnsiballZ_mail.py
 
&& sleep 0'

<localhost> EXEC /bin/sh -c 'rm -f -r 
/Users/user/.ansible/tmp/ansible-tmp-1599411608.7587368-75656-16246975542505/ 
> /dev/null 2>&1 && sleep 0'

The full traceback is:

WARNING: The below traceback may *not* be related to the actual failure.

  File 
"/var/folders/rh/bjfb4ltd1mj3_vcv8d82r5j00000gp/T/ansible_mail_payload_5Xv8cx/ansible_mail_payload.zip/ansible/modules/notification/mail.py",
 
line 316, in main

  File 
"/System/Library/Frameworks/Python.framework/Versions/2.7/lib/python2.7/smtplib.py",
 
line 623, in login

    raise SMTPAuthenticationError(code, resp)

fatal: [localhost]: FAILED! => {

    "changed": false,

    "invocation": {

        "module_args": {

            "attach": [

                "/tmp/www.example.com.zip"

            ],

            "bcc": [],

            "body": "Ansible-generated private and CSR files for 
www.example.com",

            "cc": [],

            "charset": "utf-8",

            "from": "[email protected]",

            "headers": [],

            "host": "smtp.gmail.com",

            "password": "VALUE_SPECIFIED_IN_NO_LOG_PARAMETER",

            "port": 465,

            "secure": "starttls",

            "sender": "[email protected]",

            "subject": "Private key and CSR files",

            "subtype": "plain",

            "timeout": 20,

            "to": [

                "[email protected]"

            ],

            "username": "[email protected]"

        }

    },

    "rc": 1

}


MSG:


Authentication to smtp.gmail.com:465 failed, please check your username 
and/or password


PLAY RECAP 
*********************************************************************

localhost                  : ok=4    changed=0    unreachable=0    
failed=1    skipped=0    rescued=0    ignored=0


What am I missing? I've googled to no avail.

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