FWIW, I'm also running into this, but found a work-around.  It was
suggested at
http://comments.gmane.org/gmane.linux.debian.devel.bugs.general/1172657
to edit the pg_upgradecluster script and increase the timeout from 5
seconds to 30.

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https://bugs.launchpad.net/bugs/1437862

Title:
  pg_upgradecluster fails: "could not get cluster locales"

Status in postgresql-common package in Ubuntu:
  Confirmed

Bug description:
  We upgrade a 12.04 LTS to 14.04 LTS and use the pg_upgradecluster
  command(usage as described in /usr/share/doc/README.Debian.gz). But we
  get a failure an no upgrade is done:

  pg_dropcluster 9.3 main --stop

  pg_upgradecluster 9.1 main
   psql: FATAL:  the database system is shutting down
   psql: FATAL:  the database system is shutting down
   Use of uninitialized value $out in pattern match (m//) at 
/usr/share/postgresql-common/PgCommon.pm line 883.
   psql: FATAL:  the database system is shutting down
   Use of uninitialized value $out in pattern match (m//) at 
/usr/share/postgresql-common/PgCommon.pm line 889.
   Use of uninitialized value $ctype in scalar chomp at 
/usr/share/postgresql-common/PgCommon.pm line 892.
   Use of uninitialized value $collate in scalar chomp at 
/usr/share/postgresql-common/PgCommon.pm line 893.
   Error: could not get cluster localesapt-get install postgresql-9.3

  apt-get install postgresql-9.3 postgresql-common postgresql-client-9.3
  postgresql-contrib-9.3 said, that all packages are in their newest
  version and

  dpkg said:
  iU  postgresql                          9.3+154                          all  
        object-relational SQL database (supported version)
  ii  postgresql-9.1                      9.1.15-0ubuntu0.12.04            
amd64        object-relational SQL database, version 9.1 server
  iU  postgresql-9.3                      9.3.6-0ubuntu0.14.04             
amd64        object-relational SQL database, version 9.3 server
  iU  postgresql-client                   9.3+154                          all  
        front-end programs for PostgreSQL (supported version)
  ii  postgresql-client-9.1               9.1.15-0ubuntu0.12.04            
amd64        front-end programs for PostgreSQL 9.1
  iF  postgresql-client-9.3               9.3.6-0ubuntu0.14.04             
amd64        front-end programs for PostgreSQL 9.3
  ii  postgresql-client-common            154                              all  
        manager for multiple PostgreSQL client versions
  ii  postgresql-common                   154                              all  
        PostgreSQL database-cluster manager
  iU  postgresql-contrib                  9.3+154                          all  
        additional facilities for PostgreSQL (supported version)
  ii  postgresql-contrib-9.1              9.1.15-0ubuntu0.12.04            
amd64        additional facilities for PostgreSQL
  iU  postgresql-contrib-9.3              9.3.6-0ubuntu0.14.04             
amd64        additional facilities for PostgreSQL
  ii  postgresql-doc                      9.3+154                          all  
        documentation for the PostgreSQL database management system
  ii  postgresql-doc-9.1                  9.1.15-0ubuntu0.12.04            all  
        documentation for the PostgreSQL database management system
  ii  postgresql-doc-9.3                  9.3.6-0ubuntu0.14.04             all  
        documentation for the PostgreSQL database management system

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