There is some problem with Gmail security settings. I am not sure what they 
are. It stopped working at some point less than one year ago.

I have been using spakpostmail since then with no issues:

server = smtp.sparkpostmail.com:587

sender = ****

login  = ****

tls    = true

ssl    = false



On Monday, 8 August 2016 15:07:33 UTC-5, Niphlod wrote:
>
> 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
>>>
>>

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