Why should I upgrade my Django 1.5 app to Django 1.8?

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What are the unmissable features that I'll be missing out on by sticking around with Django 1.5.

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It's not even a question of that. 1.5 is unsupported: no security updates have been made to it since the release of 1.7. There have already been several security issues raised and fixed since then, which you are missing.

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I'm a big fan of the DurationField which is modeled in Python by timedelta. You can see a full list of features here