https (SSL / TLS) by default broke apt-cacher-ng apt package caching during build

(https://github.com/Whonix/Whonix/commit/867a481710077f6bf4e14a5d8c87471e81db85df)

E: Failed to fetch https://deb.debian.org/debian-security/dists/stretch/updates/main/binary-amd64/Packages Received HTTP code 403 from proxy after CONNECT

To be expected:

https://www.unix-ag.uni-kl.de/~bloch/acng/html/howtos.html#ssluse

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.

(deb.debian.org and https by default · Kicksecure/anon-apt-sources-list@9f08431 · GitHub)

maybe if you fill that as a bug to debian , might consider to look/change something which will help the build.

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.

This issue solved long time ago, Currently everything in whonix is either pure Onion or TLS.

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This was fixed a long time ago indeed.

This was implemented. Example:

https://github.com/Whonix/Whonix/blob/master/build_sources/debian_stable_current_clearnet.list#L13

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.

Not great but there’s no better solution.

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A post was split to a new topic: Whonix build error - ERROR: Host /home/user/Whonix/build_sources/debian_stable_current_clearnet.list does not match chroot /etc/apt/sources.list