We've been talking about this today.  The question of certificates is a
rather vexed one: we'd have to put the whole bulk of ca-certificates
into the installer initrd, and furthermore many of the sites in question
are going to be self-signed ones that somebody ran up locally so there
would need to be a way to get certificates into the installer initrd.
Furthermore, if you're PXE-booting the installer, anyone can already
ARP-spoof you and substitute an installer initrd with the certificate of
their choice.  For lots of work, you gain not very much real security!

The installation guide does currently document that crypted passwords
should be an MD5 hash, but as far as I can see there's no actual
requirement for this, and a SHA-512 hash should work perfectly well.
Have you tried this?  Would this be sufficient to meet your compliance
requirements?

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https://bugs.launchpad.net/bugs/833994

Title:
  debian-installer does not support https when using with preseed files

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