Hi,
I may be mistaken, but I think it's not possible to use Gmail as a smarthost if all you have is a free account, and even if it is possible, it is hard to setup. Better try another email provider or with a paid account.
Regards,
A.
Antonis Christofides http://djangodeployment.com
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Have you enabled app in Google mail account?
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-- Jani Tiainen
Also, don't fail silently it would be helpful to see actual error
that happens...
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-- Jani Tiainen
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You might also want to read this article of mine, which might give you lots of ideas about what could be wrong: Why does Django not email me the 500 internal server error?