Oh sorry for not commenting on this.

I think the problem had to do with my configuration of daemontools. It
was configured to respawn at all runlevels making it impossible to
unmount. So I have sinced fixed the issue by fixing that.

However, there might be reason to investigate a cleaner way of handling
such situations for users not capable of taking care of it. For example
makeing sure to sync all filesystems before shutdown even if unmount
fails.

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Inconsistent filesystem on boot, possibly because of failed unmount on shutdown
https://bugs.launchpad.net/bugs/97645
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