This bug was fixed in the package ubuntu-advantage-tools -

ubuntu-advantage-tools (10ubuntu0.14.04.4) trusty; urgency=medium

  * d/control: Fix missing dependency to apt package (LP: #1840091)

 -- (Erlon R. Cruz)  Fri, 23 Aug 2019 10:12:57 -0300

** Changed in: ubuntu-advantage-tools (Ubuntu Trusty)
       Status: Fix Committed => Fix Released

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  ubuntu-advantage enable-esm should ensure correct package requirements
  are met

Status in ubuntu-advantage-tools package in Ubuntu:
  Won't Fix
Status in ubuntu-advantage-tools source package in Trusty:
  Fix Released
Status in ubuntu-advantage-tools source package in Xenial:
  Won't Fix
Status in ubuntu-advantage-tools source package in Bionic:
  Won't Fix
Status in ubuntu-advantage-tools source package in Eoan:
  Won't Fix

Bug description:

  To use ESM for 14.04 you must install 1.0.1ubuntu2.23 of apt apt-
  transport-https apt-utils libapt-inst1.5 libapt-pkg4.12

  These should be checked and warn/error/install the correct packages
  when running enable-esm

  [Test Case]

  * Deploy trusty container with a "apt" package version lower than version: 
   ** lxc launch ubuntu:d57cf522816f <CONTAINER_NAME>
      For instance image iD "d57cf522816f" contains apt : 1.0.1ubuntu2.17
  * lxc exec <CONTAINER_NAME> bash
  * Install ubuntu-advantage-tools
  * ubuntu-advantage enable-esm <token>
  * sudo apt-get update
  * sudo apt-get upgrade

  Err trusty-security/main bash amd64 
  Err trusty-security/main bzip2 amd64 
  E: Failed to fetch
  E: Failed to fetch
  E: Failed to fetch
  E: Failed to fetch
  E: Unable to fetch some archives, maybe run apt-get update or try with 

  Expected behaviour:
  Get:3 trusty-security/main bash amd64 
4.3-7ubuntu1.8+esm1 [575 kB]
  Get:6 trusty-security/main bzip2 amd64 
1.0.6-5ubuntu0.1~esm2 [34.6 kB]

  If user installs u-a-tools and do not upgrade apt, then complains are
  that it does not work all the time as expected (see above ^)

  Would be better to add some Depends: (as describe by juliank) to avoid
  users updating the tool but keeping an older version of apt that may
  introduce esm upgrade problem/failure.

  [Potential Regression]

  * One situation that Andreas brought up that is worth mentioning here,
  is  that apparently some customer may have intentionally disabled
  "trusty-updates". If it's the case, then one would need to enable
  "trusty-updates" back temporary in order to upgrade the "ubuntu-
  advantage-tools" package and it's Dependencies (apt derived binary

  * We simply instruct u-a-tools to update apt (and its derived binary
  pkg) to a more recent version to avoid problems.

  * apt in Trusty is unlikely to change now. There may be other ESM
  uploads here and there in the future, but Trusty itself is frozen now.

  [Other Info]

  * Fix has been proposed and agreed by foundation team.

  * rmadison:
   apt | 1.0.1ubuntu2            | trusty
   apt | 1.0.1ubuntu2.19         | trusty-security
   apt | 1.0.1ubuntu2.23         | trusty-updates

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