Thanks all,
a colleague of mine pointed to the solution
https://stackoverflow.com/questions/40904957/send-email-using-my-yahoo-account-error-message
some mail services require 2FA and per-app passwords

now it is working!
Umberto
Il giorno sabato 20 ottobre 2018 22:51:43 UTC+2, Sathya Narayanan ha 
scritto:
>
> Hi Umberto, 
>
> Just a quick thought, if you have any special character in your password, 
> try searching them.
>
> Some times -$ symbols are not valid when you pass that as a vatiable.
>
> I am not sure if that can fix your problem, but just a suggestion.
>
> On Fri, 19 Oct 2018, 8:25 pm Umberto Manferdini, <[email protected] 
> <javascript:>> wrote:
>
>> Hello,
>>
>> Trying to use the mail module to send emails as last task of my playbook
>>
>>  
>>
>> It fails saying
>>
>>
>> fatal: [r1 -> localhost]: FAILED! => {"changed": false, "msg": 
>> "Authentication to smtp.mail.yahoo.com:25 failed, please check your 
>> username and/or password", "rc": 1}
>>
>> even if i'm totally sure credentials are right
>>
>>  
>>
>> As I imagine, underneath, it relies on on the smtplib python module , I 
>> tried to do it manually
>>
>>  
>>
>> I get this
>>
>>  
>>
>> >>> server = smtplib.SMTP('smtp.mail.yahoo.com', 25)
>>
>>  
>>
>> >>> server.connect('smtp.mail.yahoo.com', 25)
>>
>> Traceback (most recent call last):
>>
>>   File "<stdin>", line 1, in <module>
>>
>>   File "/usr/lib/python2.7/smtplib.py", line 317, in connect
>>
>>     (code, msg) = self.getreply()
>>
>>   File "/usr/lib/python2.7/smtplib.py", line 368, in getreply
>>
>>     raise SMTPServerDisconnected("Connection unexpectedly closed")
>>
>> smtplib.SMTPServerDisconnected: Connection unexpectedly closed
>>
>>  
>>
>> >>> server.connect('smtp.mail.yahoo.com', 25)
>>
>> (220, 'smtp.mail.yahoo.com ESMTP ready')
>>
>>  
>>
>> >>> server.ehlo()
>>
>> (250, 'smtp431.mail.ir2.yahoo.com Hello*** 
>> [***])\nPIPELINING\nENHANCEDSTATUSCODES\n8BITMIME\nSIZE 41697280\nSTARTTLS')
>>
>>  
>>
>> >>> server.login("*** <javascript:>","***")
>>
>> Traceback (most recent call last):
>>
>>   File "<stdin>", line 1, in <module>
>>
>>   File "/usr/lib/python2.7/smtplib.py", line 585, in login
>>
>>     raise SMTPException("SMTP AUTH extension not supported by server.")
>>
>> smtplib.SMTPException: SMTP AUTH extension not supported by server.
>>
>>  
>>
>>    - -          I can create the object
>>    - -          First connect fails
>>    - -          Second is ok
>>    - -          Ehlo is fine
>>    - -          Login fails
>>
>>  
>>
>> Same happens with other smtp servers 
>>
>>  
>>
>> Moreover, If I try to create the server towards port 465 it fails at step 
>> 1
>>
>>  
>>
>> >>> server = smtplib.SMTP('smtp.mail.yahoo.com', 465)
>>
>> Traceback (most recent call last):
>>
>>   File "<stdin>", line 1, in <module>
>>
>>   File "/usr/lib/python2.7/smtplib.py", line 256, in __init__
>>
>>     (code, msg) = self.connect(host, port)
>>
>>   File "/usr/lib/python2.7/smtplib.py", line 317, in connect
>>
>>     (code, msg) = self.getreply()
>>
>>   File "/usr/lib/python2.7/smtplib.py", line 368, in getreply
>>
>>     raise SMTPServerDisconnected("Connection unexpectedly closed")
>>
>> smtplib.SMTPServerDisconnected: Connection unexpectedly closed
>>
>>  
>>
>> has anyone encountered this before?
>>
>>
>> task is
>>
>>
>>     - name: Sending an e-mail 
>>       mail:
>>         host: smtp.mail.yahoo.com
>>         port: 25
>>         username: "***"
>>         password: "***"
>>         to: ***
>>         subject: Ansible-report
>>         body: "report generated"
>>         attach:
>>           - "sanity_report.csv"
>>           - "{{playbook_dir}}/outputs.tgz"
>>       delegate_to: localhost
>>
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