How to activate/renew Ubuntu Advantage/ESM if you have HTTP connect proxy like Squid?

Question

How to activate/renew Ubuntu Advantage/ESM on Ubuntu 14.04 if you have HTTP connect proxy like Squid - so you get security updates again? With the older tool I get errors and/or timeouts with sudo apt update && sudo apt dist-upgrade.

Answer 1

In the meantime, I found out for myself:

cat /etc/apt/apt.conf  # check for proxy FQDN! Or create empty file!
cat /etc/environment  # check for proxy FQDN!
sudo rm /etc/apt/sources.list.d/ubuntu-esm-infra.list
sudo apt update
sudo -E add-apt-repository ppa:ua-client/stable  # press Enter
sudo apt update
sudo apt install --reinstall ubuntu-advantage-tools
sudo -E ua status
sudo -E ua detach  # optional
sudo -E ua attach <ID_VIA_SEE_IMAGE_BELOW>
sudo -E ua enable esm-infra
sudo -E ua status
sudo update
sudo apt dist-upgrade

https://support.canonical.com/selfservice/s/article/Obtaining-ESM-Credentials-And-Enabling-ESM-On-Ubuntu-14-04-LTS-Trusty

Also interesting:

# Livepatch with Ubuntu 14 und Ubuntu 16
# Sometimes sudo isn't enough -> sometimes you need a real root terminal!
#
sudo -E canonical-livepatch config http-proxy=http://<HOST>:<PORT>
sudo -E canonical-livepatch config https-proxy=http://<HOST>:<PORT>
#
sudo -E ua enable livepatch

# Landscape with Ubuntu 14 und Ubuntu 16
# sudo apt update
sudo apt --yes install landscape-client
sudo -E landscape-config -a <SUBSCRIPTION_NAME> -t $(hostname -f)
# Enter (Y)
# Enter (no Account-Registration-Key)
# Enter (HTTP-Proxy)
# Enter (HTTPS-Proxy)
# y (activate scripts)
# ALL (scripts for all)
# Enter (no Access-Group)
# Leave empty or continuous_use, reboot_ok, reboot_stops (tags)
# Enter (Y)

Answer 2

I'm trying to use ESM with my "good-old" ubuntu xenial (16.04) until I'll find time to upgrade to newer version.

I've tried to setup ESM multiple times and again with your instructions above. But anytime I'm getting 401 unauthorized error with apt-get/aptitude trying to install updates available for ESM packages available.

My subscription is active and valid showing 1 subscription active. Obviously no one can say why I'm still getting 401 unauthorized! And Ubuntu/Support refuses to help as they are only interested in selling not supporting.