Public bug reported:

$ lsb_release -rd
Description:    Ubuntu 14.04.6 LTS
Release:        14.04

$ apt-cache policy ubuntu-advantage-tools
ubuntu-advantage-tools:
  Installed: 19.6~ubuntu14.04.3
  Candidate: 19.6~ubuntu14.04.3
  Version table:
 *** 19.6~ubuntu14.04.3 500
        500 http://archive.ubuntu.com/ubuntu trusty-updates/main amd64 Packages
        100 /var/lib/dpkg/status

$ sudo ua status
SERVICE       ENTITLED  STATUS    DESCRIPTION
cc-eal        yes       n/a       Common Criteria EAL2 Provisioning Packages
cis-audit     no        —         Center for Internet Security Audit Tools
esm-infra     yes       enabled   UA Infra: Extended Security Maintenance
fips          yes       n/a       NIST-certified FIPS modules
fips-updates  yes       n/a       Uncertified security updates to FIPS modules
livepatch     yes       n/a       Canonical Livepatch service

Enable services with: ua enable <service>

     Account: (redacted)
Subscription: (redacted)

=======
Problem
=======

$ sudo apt upgrade -y
Reading package lists... Done
Building dependency tree
Reading state information... Done
Calculating upgrade... Done
The following packages will be upgraded:
  apport apport-gtk aspell bash bind9-host bzip2 cabextract cpio curl dbus 
dbus-x11 dnsutils e2fslibs e2fsprogs file initscripts krb5-locales
  libarchive13 libaspell15 libass4 libbind9-90 libbz2-1.0 libbz2-dev libc-bin 
libc-dev-bin libc6 libc6-dbg libc6-dev libc6-i386 libcomerr2 libcurl3
  libcurl3-gnutls libdb5.3 libdb5.3-dev libdbus-1-3 libdns100 libexpat1 
libexpat1-dev libfreetype6 libfreetype6-dev libglib2.0-0 libglib2.0-bin
  libglib2.0-data libglib2.0-dev libgme0 libgssapi-krb5-2 libisc95 libisccc90 
libisccfg90 libk5crypto3 libkrb5-3 libkrb5support0 libldap-2.4-2
  liblwres90 libmagic1 libmpg123-0 libnss3 libnss3-1d libnss3-nssdb libpcap0.8 
libpython2.7 libpython2.7-minimal libpython2.7-stdlib libpython3.4
  libpython3.4-dev libpython3.4-minimal libpython3.4-stdlib libsdl1.2debian 
libsmbclient libsoundtouch0 libsqlite3-0 libsqlite3-dev libss2
  libwbclient0 libxslt1.1 multiarch-support ntp ntpdate patch python-samba 
python-urllib3 python-urllib3-whl python2.7 python2.7-minimal
  python3-apport python3-problem-report python3-urllib3 python3.4 python3.4-dev 
python3.4-minimal samba-common samba-common-bin samba-libs screen
  smbclient sqlite3 sudo sysv-rc sysvinit-utils tzdata tzdata-java 
vivaldi-stable wpasupplicant xsltproc
104 upgraded, 0 newly installed, 0 to remove and 0 not upgraded.
Need to get 68.6 MB/133 MB of archives.
After this operation, 5,832 kB of additional disk space will be used.
Err:1 https://esm.ubuntu.com/ubuntu trusty-infra-security/main amd64 bash amd64 
4.3-7ubuntu1.8+esm1
  401  Unauthorized
Err:2 https://esm.ubuntu.com/ubuntu trusty-infra-security/main amd64 libc6-dbg 
amd64 2.19-0ubuntu6.15+esm1
  401  Unauthorized
Err:3 https://esm.ubuntu.com/ubuntu trusty-infra-security/main amd64 libc6-i386 
amd64 2.19-0ubuntu6.15+esm1
  401  Unauthorized
Err:4 https://esm.ubuntu.com/ubuntu trusty-infra-security/main amd64 libc6-dev 
amd64 2.19-0ubuntu6.15+esm1
  401  Unauthorized
Err:5 https://esm.ubuntu.com/ubuntu trusty-infra-security/main amd64 
libc-dev-bin amd64 2.19-0ubuntu6.15+esm1
  401  Unauthorized
Err:6 https://esm.ubuntu.com/ubuntu trusty-infra-security/main amd64 libc-bin 
amd64 2.19-0ubuntu6.15+esm1
  401  Unauthorized
Err:7 https://esm.ubuntu.com/ubuntu trusty-infra-security/main amd64 libc6 
amd64 2.19-0ubuntu6.15+esm1
  401  Unauthorized
(truncated)

===========
Expectation
===========

According to https://wiki.ubuntu.com/UAclient
the 'sudo apt upgrade' should go without a hitch.

Why are the https credentials missing?

** Affects: ubuntu-advantage-tools (Ubuntu)
     Importance: Undecided
         Status: New

** Description changed:

  $ lsb_release -rd
  Description:  Ubuntu 14.04.6 LTS
  Release:      14.04
  
  $ apt-cache policy ubuntu-advantage-tools
  ubuntu-advantage-tools:
-   Installed: 19.6~ubuntu14.04.3
-   Candidate: 19.6~ubuntu14.04.3
-   Version table:
-  *** 19.6~ubuntu14.04.3 500
-         500 http://archive.ubuntu.com/ubuntu trusty-updates/main amd64 
Packages
-         100 /var/lib/dpkg/status
+   Installed: 19.6~ubuntu14.04.3
+   Candidate: 19.6~ubuntu14.04.3
+   Version table:
+  *** 19.6~ubuntu14.04.3 500
+         500 http://archive.ubuntu.com/ubuntu trusty-updates/main amd64 
Packages
+         100 /var/lib/dpkg/status
  
  $ sudo ua status
  SERVICE       ENTITLED  STATUS    DESCRIPTION
  cc-eal        yes       n/a       Common Criteria EAL2 Provisioning Packages
  cis-audit     no        —         Center for Internet Security Audit Tools
  esm-infra     yes       enabled   UA Infra: Extended Security Maintenance
  fips          yes       n/a       NIST-certified FIPS modules
  fips-updates  yes       n/a       Uncertified security updates to FIPS modules
  livepatch     yes       n/a       Canonical Livepatch service
  
  Enable services with: ua enable <service>
  
-      Account: kfrdbs+ubu...@gmail.com
- Subscription: kfrdbs+ubu...@gmail.com
+      Account: (redacted)
+ Subscription: (redacted)
  
  =======
  Problem
  =======
  
  $ sudo apt upgrade -y
  Reading package lists... Done
- Building dependency tree       
+ Building dependency tree
  Reading state information... Done
  Calculating upgrade... Done
  The following packages will be upgraded:
-   apport apport-gtk aspell bash bind9-host bzip2 cabextract cpio curl dbus 
dbus-x11 dnsutils e2fslibs e2fsprogs file initscripts krb5-locales
-   libarchive13 libaspell15 libass4 libbind9-90 libbz2-1.0 libbz2-dev libc-bin 
libc-dev-bin libc6 libc6-dbg libc6-dev libc6-i386 libcomerr2 libcurl3
-   libcurl3-gnutls libdb5.3 libdb5.3-dev libdbus-1-3 libdns100 libexpat1 
libexpat1-dev libfreetype6 libfreetype6-dev libglib2.0-0 libglib2.0-bin
-   libglib2.0-data libglib2.0-dev libgme0 libgssapi-krb5-2 libisc95 libisccc90 
libisccfg90 libk5crypto3 libkrb5-3 libkrb5support0 libldap-2.4-2
-   liblwres90 libmagic1 libmpg123-0 libnss3 libnss3-1d libnss3-nssdb 
libpcap0.8 libpython2.7 libpython2.7-minimal libpython2.7-stdlib libpython3.4
-   libpython3.4-dev libpython3.4-minimal libpython3.4-stdlib libsdl1.2debian 
libsmbclient libsoundtouch0 libsqlite3-0 libsqlite3-dev libss2
-   libwbclient0 libxslt1.1 multiarch-support ntp ntpdate patch python-samba 
python-urllib3 python-urllib3-whl python2.7 python2.7-minimal
-   python3-apport python3-problem-report python3-urllib3 python3.4 
python3.4-dev python3.4-minimal samba-common samba-common-bin samba-libs screen
-   smbclient sqlite3 sudo sysv-rc sysvinit-utils tzdata tzdata-java 
vivaldi-stable wpasupplicant xsltproc
+   apport apport-gtk aspell bash bind9-host bzip2 cabextract cpio curl dbus 
dbus-x11 dnsutils e2fslibs e2fsprogs file initscripts krb5-locales
+   libarchive13 libaspell15 libass4 libbind9-90 libbz2-1.0 libbz2-dev libc-bin 
libc-dev-bin libc6 libc6-dbg libc6-dev libc6-i386 libcomerr2 libcurl3
+   libcurl3-gnutls libdb5.3 libdb5.3-dev libdbus-1-3 libdns100 libexpat1 
libexpat1-dev libfreetype6 libfreetype6-dev libglib2.0-0 libglib2.0-bin
+   libglib2.0-data libglib2.0-dev libgme0 libgssapi-krb5-2 libisc95 libisccc90 
libisccfg90 libk5crypto3 libkrb5-3 libkrb5support0 libldap-2.4-2
+   liblwres90 libmagic1 libmpg123-0 libnss3 libnss3-1d libnss3-nssdb 
libpcap0.8 libpython2.7 libpython2.7-minimal libpython2.7-stdlib libpython3.4
+   libpython3.4-dev libpython3.4-minimal libpython3.4-stdlib libsdl1.2debian 
libsmbclient libsoundtouch0 libsqlite3-0 libsqlite3-dev libss2
+   libwbclient0 libxslt1.1 multiarch-support ntp ntpdate patch python-samba 
python-urllib3 python-urllib3-whl python2.7 python2.7-minimal
+   python3-apport python3-problem-report python3-urllib3 python3.4 
python3.4-dev python3.4-minimal samba-common samba-common-bin samba-libs screen
+   smbclient sqlite3 sudo sysv-rc sysvinit-utils tzdata tzdata-java 
vivaldi-stable wpasupplicant xsltproc
  104 upgraded, 0 newly installed, 0 to remove and 0 not upgraded.
  Need to get 68.6 MB/133 MB of archives.
  After this operation, 5,832 kB of additional disk space will be used.
- Err:1 https://esm.ubuntu.com/ubuntu trusty-infra-security/main amd64 bash 
amd64 4.3-7ubuntu1.8+esm1                                                  
-   401  Unauthorized
+ Err:1 https://esm.ubuntu.com/ubuntu trusty-infra-security/main amd64 bash 
amd64 4.3-7ubuntu1.8+esm1
+   401  Unauthorized
  Err:2 https://esm.ubuntu.com/ubuntu trusty-infra-security/main amd64 
libc6-dbg amd64 2.19-0ubuntu6.15+esm1
-   401  Unauthorized
+   401  Unauthorized
  Err:3 https://esm.ubuntu.com/ubuntu trusty-infra-security/main amd64 
libc6-i386 amd64 2.19-0ubuntu6.15+esm1
-   401  Unauthorized
+   401  Unauthorized
  Err:4 https://esm.ubuntu.com/ubuntu trusty-infra-security/main amd64 
libc6-dev amd64 2.19-0ubuntu6.15+esm1
-   401  Unauthorized
+   401  Unauthorized
  Err:5 https://esm.ubuntu.com/ubuntu trusty-infra-security/main amd64 
libc-dev-bin amd64 2.19-0ubuntu6.15+esm1
-   401  Unauthorized
+   401  Unauthorized
  Err:6 https://esm.ubuntu.com/ubuntu trusty-infra-security/main amd64 libc-bin 
amd64 2.19-0ubuntu6.15+esm1
-   401  Unauthorized
+   401  Unauthorized
  Err:7 https://esm.ubuntu.com/ubuntu trusty-infra-security/main amd64 libc6 
amd64 2.19-0ubuntu6.15+esm1
-   401  Unauthorized
+   401  Unauthorized
  (truncated)
  
  ===========
  Expectation
  ===========
  
  According to https://wiki.ubuntu.com/UAclient
  the 'sudo apt upgrade' should go without a hitch.
  
  Why are the https credentials missing?

** Summary changed:

- UA attached but 401 error when apt upgrade
+ UA attached but 401 error when apt upgrade for 14.04 esm-infra

** Summary changed:

- UA attached but 401 error when apt upgrade for 14.04 esm-infra
+ UA enabled for 14.04 esm-infra but 401 error when apt upgrade

-- 
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https://bugs.launchpad.net/bugs/1859318

Title:
  UA enabled for 14.04 esm-infra but 401 error when apt upgrade

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