Sorry for the late response
There is definitly a different if I use web2py  shell source  to send mail 
or web2py.exe
It works fine with source and failes with web2py.exe
My python installation is 2.7.13
here is my source execution :
C:\Temp\web2py_src\web2py>python web2py.py -S welcome
No handlers could be found for logger "web2py"
web2py Web Framework
Created by Massimo Di Pierro, Copyright 2007-2017
Version 2.14.6-stable+timestamp.2016.05.10.00.21.47
Database drivers available: psycopg2, pymysql, imaplib, sqlite3, pg8000, 
pyodbc
WARNING:web2py:import IPython error; use default python shell
Python 2.7.13 (v2.7.13:a06454b1afa1, Dec 17 2016, 20:42:59) [MSC v.1500 32 
bit (Intel)] on win32
Type "help", "copyright", "credits" or "license" for more information.
(InteractiveConsole)
>>> variables= {}
>>> execfile( "/temp/mailtest.py", variables )
{u'total_accepted_recipients': 1, u'id': u'48590550571575300', 
u'total_rejected_recipients': 0}
>>>

and here is with web2py.exe
Enter code here...>>> variables= {}
>>> execfile( "/temp/mailtest.py", variables )
Traceback (most recent call last):
  File "<console>", line 1, in <module>
  File "/temp/mailtest.py", line 10, in <module>
    subject='Hello from python-sparkpost'
  File "C:\Python27\lib\site-packages\sparkpost\transmissions.py", line 
254, in send
    results = self.request('POST', self.uri, data=json.dumps(payload))
  File "C:\Python27\lib\site-packages\sparkpost\base.py", line 41, in 
request
    **kwargs)
  File "C:\Python27\lib\site-packages\sparkpost\base.py", line 12, in 
request
    response = self.sess.request(method, uri, headers=headers, **kwargs)
  File "C:\Python27\lib\site-packages\requests\sessions.py", line 513, in 
request
    resp = self.send(prep, **send_kwargs)
  File "C:\Python27\lib\site-packages\requests\sessions.py", line 623, in 
send
    r = adapter.send(request, **kwargs)
  File "C:\Python27\lib\site-packages\requests\adapters.py", line 514, in 
send
    raise SSLError(e, request=request)
SSLError: [SSL: CERTIFICATE_VERIFY_FAILED] certificate verify failed 
(_ssl.c:581)
>>>




On Sunday, June 11, 2017 at 10:08:58 AM UTC+2, Massimo Di Pierro wrote:
>
> First of all I recommend you configure sparkpost using web2py auth.mailer 
> SMTP else you do not get the benefit of auth email logic.
>
> Also, I recommend you run web2py from source, not the windows binary. I 
> will give you more control. If you find that running from source makes the 
> problem go away, please let us know.
>
> Massimo
>
> On Friday, 9 June 2017 02:48:55 UTC-5, icodk wrote:
>>
>> Sparkpost has simple python api:
>>
>> from sparkpost import SparkPost
>> sp = SparkPost('YOUR API KEY')
>>
>> response = sp.transmissions.send(
>>     use_sandbox=True,
>>     recipients=['som...@somedomain.com <javascript:>'],
>>     html='<p>Hello world</p>',
>>     from_email='te...@sparkpostbox.com <javascript:>',
>>     subject='Hello from python-sparkpost'
>> )
>>
>> print(response)
>>
>>
>> However I get the following error:
>> SSLError: [SSL: CERTIFICATE_VERIFY_FAILED] certificate verify failed (
>> _ssl.c:581)
>>
>> Could be something with the python version  in web2py.exe (I am useing 
>>  web2py_2_14_06)
>> Any idea
>>
>

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