Tell you the truth I have given up using gmail for sending emails. 
Authentication is a nightmare and they seem to change the rules often.  I 
would recommend SparkPost instead.



On Tuesday, 22 March 2016 10:51:36 UTC-5, killzane wrote:
>
> Hello,
>
> I can send mail from my controller.
>
> but I face another problem.
> When I use python example send mail to Gmail, It works.
> but when I use my web2py controller send it, Gmail let it bounced.
>
> This is in mail.log
> to=<reciver mail>, relay=gmail-smtp-in.l.google.com[2404:6800:4003:c02::1b
> ]:25, delay=2.1, delays=0.01/0.01/0.51/1.6, dsn=5.7.1, status=bounced (host 
> gmail-smtp-in.l.google.com[2404:6800:4003:c02::1b] said: 550-5.7.1 [2400:
> 8901::f03c:91ff:fee4:d079] Our system has detected that this 550-5.7.1 
> message does not meet IPv6 sending guidelines regarding PTR records 550-
> 5.7.1 and authentication. Please review 550-5.7.1  https://
> support.google.com/mail/?p=ipv6_authentication_error for more 550 5.7.1 
> information. f199si13418465oig.91 - gsmtp (in reply to end of DATA command))
>
> I have set Reverse DNS for my server. but only python example can work.
>
> Here is my server data.
>     Ubuntu 15.04 (GNU/Linux 4.4.0-x86_64-linode63 x86_64)
>
>
> Anthony於 2015年9月1日星期二 UTC+8上午9時37分20秒寫道:
>>
>> Please answer the questions you were asked here: 
>> http://stackoverflow.com/questions/32023493/why-i-can-sen-mail-use-python-but-cant-send-by-web2py-mail-object#comment52023284_32023493
>>
>> On Monday, August 31, 2015 at 9:00:45 PM UTC-4, killzane wrote:
>>>
>>> As title.
>>> I can send mail via this example.
>>> 18.1.11. email: Examples 
>>> <https://docs.python.org/2/library/email-examples.html>
>>>
>>> But when I use web2py framework and follow this guide
>>> Email and SMS 
>>> <http://web2py.com/books/default/chapter/34/08/email-and-sms#Sending-messages-using-a-background-task>
>>>
>>> I can't send my mail and I don't have any log on my smtp server.
>>>
>>> Here is the web2py controller code
>>>
>>> def helloMail():
>>>     view = _VIEW_VARIABLES
>>>     response.view = 'testMail.html'
>>>     mail = Mail()
>>>     mail.settings.server = 'localhost'
>>>     mail.settings.sender = 'sendermail'
>>>     mail.settings.login = None
>>>     mailListener = mail.send(to=['reciver mail'],
>>>       subject='hello',
>>>       message='hi there')
>>>
>>>     return dict(view=view, mailListener = mailListener)
>>>
>>> Please help me to send mail by web2py. 
>>> P.S. I also use local SMTP in python code
>>>
>>

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