the "usual" issues are: 
- gmail's newer "secure apps" enabled by default which requires a two-step 
verification, which smtplib can't handle
- tls or ssl enabled (or disabled) and the smtp endpoint not "in tune" with 
web2py's settings

I'm also pretty sure that the traceback kinda steers towards the right 
direction in the second case.

On Monday, August 8, 2016 at 9:12:16 PM UTC+2, Valdeck Rowe wrote:
>
> Hi
>
> I've never gotten the smtp interface in web2py to work either.
>
> It just simply does not appear to work with Google or with Mailgun. I 
> always end up using the mailgun api.
>
> I'm not sure what I'm missing but its a bit frustrating, especially 
> considering that I'm trying to sell them on web2py at work.
>
> What's interesting is that I'm able to connect to the mailgun smtp via 
> telnet, so I doubt its the port information.
>
> I'm using the username and password copied directly from the mailgun 
> domain page.
>
> I'm not sure what the problem is. Any suggestions at this point would be 
> sincerely appreciated.
>
> Thanks.
>
>
> On Friday, February 12, 2016 at 2:38:38 PM UTC-5, Tom Russell wrote:
>>
>> I have since my last time trying to get email sending working with the 
>> built in registration process moved to Amazon AWS SES mail services which I 
>> know works well with other people. I have put in all the required info in 
>> db.py needed but still cannot send an email. I have tried gmail, a few 
>> other services and nothing so far seems to work.
>>
>> Has anyone tried an actual mail service that works, preferably free or 
>> close to it. I am beginning to think that web2py has an issue doing this 
>> task.
>>
>> I really need to get past this hurtle for a product launch soon.
>>
>> Thanks,
>>
>> Tom
>>
>

-- 
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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