I will try provide a more details answer but for now this is what I know:

1) mail.send(...) returns True or False so you can check if the email was 
sent
2) mail.send uses SMTP with logs errors using a logger. This means there is 
no ticket but you use a logger as explained here, you should be able to 
capture them. https://stackoverflow.com/questions/19787198/logging-in-web2py

I have not tried 2 myself.

On Sunday, 4 June 2017 11:04:47 UTC-5, e27...@gmail.com wrote:
>
> Hello everyone.
>
> I am quite desperate. I can not send email using smtp.gmail.com. Nothing 
> seams to be working. I use a gmail smtp account which is working fine on my 
> server when I use a basic python script, or even a php script on my Apache 
> 2.4. But is not not working with Web2py. I do not have the 2 identification 
> activated on gmail.
>
>
>
> *What i did : *I created a news application. In the db.py file, I have 
> put the following lines :
>
> from gluon.tools import Auth, Service, PluginManager
>
> auth = Auth(db)
> service = Service()
> plugins = PluginManager()
>
> ## create all tables needed by auth if not custom tables
> auth.define_tables(username=False, signature=False)
>
> ## configure email
> mail = auth.settings.mailer
> mail.settings.server = 'smtp.gmail.com:587'
> mail.settings.sender = 'exx...@gmail.com'
> mail.settings.login = 'exx...@gmail.com:XXXXX'
>
>
> In the default.py file, I just put the following line :
>
> def index():
>
>     mail.send('exx...@gmail.com','Subject','Message')
>    
>     response.flash = T("Hello World")
>     return dict(message=T('Welcome to web2py!'))
>
>
> I have not error messages, but no mail was sent.
>
> Any idea ?
>
> Thank you very much.
>
> ------------------
> Version 
>
> 2.14.6-stable+timestamp.2016.05.10.00.21.47
> (Running on Apache/2.4.23 (Win32) OpenSSL/1.0.2h PHP/7.0.10 
> mod_wsgi/4.4.12 Python/2.7.10, Python 2.7.10) 
>
>
>

-- 
Resources:
- http://web2py.com
- http://web2py.com/book (Documentation)
- http://github.com/web2py/web2py (Source code)
- https://code.google.com/p/web2py/issues/list (Report Issues)
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