Perhaps the "tell-me-what-you-need method" mentioned there would help.
This makes also enabling https (SSL / TLS) in anon-apt-soures-list (/etc/apt/sources.list.d/debian.list) difficult. "tell-me-what-you-need method" is hard to add in /etc/apt/sources.list.d/debian.list but it is being used during build of Whonix.
Not a Debian bug. Known and documented limitation. An (apt package)
caching proxy can’t cache end-to-end encrypted SSL’ed connections by
design. Not easy without hacks.
many distros that i know use ssl by default for their repos like parrotsec, trisquel…etc so maybe check their code or how they implemented that and see if it can fit to our distro.
APT sources during build (chroot) (build_sources) and APT sources used when actually booting a VM (anon-apt-sources-list) are using the same APT repositories (manually keeping sync) but different format.