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Good start indeed, it'd be nice to have a small open source tool to do these checks, maybe even with a simple web interface - anyone seen a simple security checklist / analyser that's well maintained with the latest standards?

SSL labs is the gold standard:

https://www.ssllabs.com/ssltest/

But I don't see a way to automate a test for the integrity of (say) a password recovery flow or that one user cannot access another user's data.

Yeah that's what I use at present, if it's not an A+ it's not OK. Would be nice to have an open source version of this that could perform additional checks though.

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