It seems to me that Google SMTP server service is not so friendly.
I gave up trying to work with it some time ago.  
I recommend that either you use your own ISP's server,  or search for a 
professional solution.  We have been very happy with fastmail.fm but there 
are many other low-cost or free solutions.

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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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