The documentation of Redmine describes the upgrade process. I upgraded from Redmine 1.3.1 to Redmine 2.2.2. On an older Ubuntu (10.04.4 LTS) the upgrade steps described in the documentation were not sufficient.

Extract the latest redmine file in your web root. I use a symlink pointing redmine to the latest version. This allows you to keep different version and provides an easy way to switch between versions. You then have to copy the different configuration files (database, configuration) from the ‘old’ setup to the ‘new’ setup. Do not copy the settings.yml file.

cp redmine-1.3.1/config/database.yml redmine/config/
cp -r redmine-1.3.1/files redmine/

The first error message is because of bundle.

rake aborted!
no such file to load -- bundler/setup

gem install bundler
bundle install

The bundle command failed because of libmagick problems. It was not a requirement for older Redmine versions but without the package (and the libraries) I couldn’t get the upgrade to continue.

checking for Magick-config... no
Can't install RMagick 2.13.2. Can't find Magick-config in /usr/local/sbin:/usr/local/bin:/usr/sbin:/usr/bin:/sbin:/bin:/usr/X11R6/bin

apt-get install librmagick-ruby
apt-get install libmagick9-dev

Restart the bundle install.

bundle install

Perform the ‘normal’ migration steps.

rake generate_secret_token
rake db:migrate RAILS_ENV=production
rake redmine:plugins:migrate RAILS_ENV=production 
rake tmp:cache:clear
rake tmp:sessions:clear

Restart Apache (and Passenger). The next error was Ruby (browser) complaining that there was no dispatch file.

no such file to load -- dispatcher

To solve this you have to upgrade Passenger manually.

gem install passenger
passenger-install-apache2-module

Change these configuration files

in /etc/apache2/mods-enabled/passenger.load
  LoadModule passenger_module /usr/lib/ruby/gems/1.8/gems/passenger-3.0.19/ext/apache2/mod_passenger.so

in /etc/apache2/mods-enabled/passenger.conf
  PassengerRoot /usr/lib/ruby/gems/1.8/gems/passenger-3.0.19
  PassengerRuby /usr/bin/ruby1.8

Restart Apache and Passenger. Log in to Redmine and go to the Administration part and review the roles and configuration.

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