I am trying to send emails from Django using an email configured by Google Apps, my configuration at the settings.py file looks something like this:
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Recently, I have found that this issue can be resolved by confirming that the activity has originated from a request I initiated, by visiting Google Account
I had to confirm, under Security Events, that the suspicious activity was in-fact me, even though the originating server from where the request came from was cloud hosted, and therefore over 1000 km away. After clicking this step, and setting less secure apps, I was able to use getmail to retrieve my mail, over ssl using either imap or pop.