I've been there

>It's not my boss that's the problem - it's the environment as a whole.

How exactly will outdated docs keep you safe in an audit?

>We might get audited, so we need to have documentation available", but the documentation is not kept up to date and is quickly outdated.

It's a common misconception that Agile = no documentation. What it really means is that you create little documentation. Just enough to do the job.

>Agile development is a dirty word around here.