Public bug reported:

Following the instructions to add the docker repo here:
https://docs.docker.com/engine/installation/linux/ubuntu/

/etc/apt/sources.list contains the repo: 
deb https://apt.dockerproject.org/repo/ ubuntu-xenial main

When running through apt-cacher-ng, apt-get update returns: 
$ sudo apt-get update
Ign:1 https://apt.dockerproject.org/repo ubuntu-xenial InRelease
Ign:2 https://apt.dockerproject.org/repo ubuntu-xenial Release
Ign:3 https://apt.dockerproject.org/repo ubuntu-xenial/main amd64 
Packages.diff/Index
Ign:4 https://apt.dockerproject.org/repo ubuntu-xenial/main i386 Packages
Ign:5 https://apt.dockerproject.org/repo ubuntu-xenial/main all Packages
Ign:6 https://apt.dockerproject.org/repo ubuntu-xenial/main Translation-en_US
Ign:7 https://apt.dockerproject.org/repo ubuntu-xenial/main Translation-en
Ign:8 https://apt.dockerproject.org/repo ubuntu-xenial/main amd64 Packages
Ign:4 https://apt.dockerproject.org/repo ubuntu-xenial/main i386 Packages
Ign:5 https://apt.dockerproject.org/repo ubuntu-xenial/main all Packages
Ign:6 https://apt.dockerproject.org/repo ubuntu-xenial/main Translation-en_US
Ign:7 https://apt.dockerproject.org/repo ubuntu-xenial/main Translation-en
Ign:8 https://apt.dockerproject.org/repo ubuntu-xenial/main amd64 Packages
Ign:4 https://apt.dockerproject.org/repo ubuntu-xenial/main i386 Packages
Ign:5 https://apt.dockerproject.org/repo ubuntu-xenial/main all Packages
Ign:6 https://apt.dockerproject.org/repo ubuntu-xenial/main Translation-en_US
Ign:7 https://apt.dockerproject.org/repo ubuntu-xenial/main Translation-en
Ign:8 https://apt.dockerproject.org/repo ubuntu-xenial/main amd64 Packages
Ign:4 https://apt.dockerproject.org/repo ubuntu-xenial/main i386 Packages
Ign:5 https://apt.dockerproject.org/repo ubuntu-xenial/main all Packages
Ign:6 https://apt.dockerproject.org/repo ubuntu-xenial/main Translation-en_US
Ign:7 https://apt.dockerproject.org/repo ubuntu-xenial/main Translation-en
Ign:8 https://apt.dockerproject.org/repo ubuntu-xenial/main amd64 Packages
Ign:4 https://apt.dockerproject.org/repo ubuntu-xenial/main i386 Packages
Ign:5 https://apt.dockerproject.org/repo ubuntu-xenial/main all Packages
Ign:6 https://apt.dockerproject.org/repo ubuntu-xenial/main Translation-en_US
Ign:7 https://apt.dockerproject.org/repo ubuntu-xenial/main Translation-en
Ign:8 https://apt.dockerproject.org/repo ubuntu-xenial/main amd64 Packages
Err:4 https://apt.dockerproject.org/repo ubuntu-xenial/main i386 Packages
  Received HTTP code 403 from proxy after CONNECT
Ign:5 https://apt.dockerproject.org/repo ubuntu-xenial/main all Packages
Ign:6 https://apt.dockerproject.org/repo ubuntu-xenial/main Translation-en_US
Ign:7 https://apt.dockerproject.org/repo ubuntu-xenial/main Translation-en
Ign:8 https://apt.dockerproject.org/repo ubuntu-xenial/main amd64 Packages
Ign:9 http://dl.google.com/linux/chrome/deb stable InRelease
Hit:10 http://archive.ubuntu.com/ubuntu xenial InRelease
Hit:11 http://dl.google.com/linux/chrome/deb stable Release              
Hit:13 http://archive.ubuntu.com/ubuntu xenial-updates InRelease
Hit:14 http://archive.ubuntu.com/ubuntu xenial-security InRelease
Reading package lists... Done
W: The repository 'https://apt.dockerproject.org/repo ubuntu-xenial Release' 
does not have a Release file.
N: Data from such a repository can't be authenticated and is therefore 
potentially dangerous to use.
N: See apt-secure(8) manpage for repository creation and user configuration 
details.
E: Failed to fetch 
https://apt.dockerproject.org/repo/dists/ubuntu-xenial/main/binary-i386/Packages
  Received HTTP code 403 from proxy after CONNECT
E: Some index files failed to download. They have been ignored, or old ones 
used instead.


When apt is set to disable the proxy, using the following /etc/apt/apt.conf:
Acquire::http::Proxy "http://127.0.0.1:9999/";;
Acquire::https::Proxy "DIRECT";

(note that the port has been changed from the default)

The response is:
$ sudo apt-get update
Hit:1 https://apt.dockerproject.org/repo ubuntu-xenial InRelease
Ign:2 http://dl.google.com/linux/chrome/deb stable InRelease             
Hit:3 http://archive.ubuntu.com/ubuntu xenial InRelease
Hit:4 http://dl.google.com/linux/chrome/deb stable Release              
Hit:6 http://archive.ubuntu.com/ubuntu xenial-updates InRelease
Hit:7 http://archive.ubuntu.com/ubuntu xenial-security InRelease
Reading package lists... Done


$lsb_release -rd
Description:    Ubuntu 16.04.1 LTS
Release:        16.04
$ apt-cache policy apt-cacher-ng
apt-cacher-ng:
  Installed: 0.9.1-1ubuntu1
  Candidate: 0.9.1-1ubuntu1
  Version table:
 *** 0.9.1-1ubuntu1 500
        500 http://archive.ubuntu.com/ubuntu xenial/universe amd64 Packages
        100 /var/lib/dpkg/status

** Affects: apt-cacher-ng (Ubuntu)
     Importance: Undecided
         Status: New

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https://bugs.launchpad.net/bugs/1661199

Title:
  Apt-cacher-ng fails on https repo

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