Devin Cofer wrote on 4/9/19 5:04 PM:
Hello all,

Recently my Qubes 4 installation's debian template and whonix templates stopped 
updating correctly.

Fedora-based templates and Dom0 update fine.

`sudo apt update` on debian template will error when it tries to fetch 
jessie-backports Release.

....
Err:7 https://cdn-aws.deb.debian.org/debian jessie-backports Release
   404  Not Found
Reading package lists... Done
E: The repository 'https://deb.debian.org/debian jessie-backports Release' does 
not have a Release file.
N: Updating from such a repository can't be done securely, and is therefore 
disabled by default.
....

On whonix templates, `sudo apt update` stalls at "0% [Waiting for headers]" for 
a long time, then proceeds until it hits other errors.

....
Err:4 https://deb.whonix.org stretch Release
   Received HTTP code 500 from proxy after CONNECT
Err:5 https://deb.qubes-os.org/r4.0/vm stretch Release
   Received HTTP code 500 from proxy after CONNECT
Ign:6 https://deb.debian.org/debian stretch InRelease
Err:7 https://deb.debian.org/debian-security stretch/updates Release
   Received HTTP code 500 from proxy after CONNECT
Err:8 https://deb.debian.org/debian stretch Release
   Received HTTP code 500 from proxy after CONNECT
....

I typed this out, so excuse any spelling mistakes in the command output.

Thanks for any assistance!

See this recent thread: https://www.mail-archive.com/[email protected]/msg27443.html. TLDR, comment out that jessie-backports line in apt sources in the problem templates.

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