Redmine - Upgrade to 1.4.4 on a debian squeeze

This document describes how to upgrade Redmine. The procedure was tested for upgrade from version 1.0.1 to 1.4.4, but it might works on other Redmine versions.
In this procedure I used a basic install of a debian squeeze (the only service installed was openssh-server). I am assuming the server has network connectivity and its IP is

Please note:
- please announce all people BEFORE starting this procedure
- the Apache server on production environment MUST be stopped so after the upgrade the database be in sync.
- this version of Redmine needs ruby version 1.8.7 or 1.9.3 (I am going to use the debian squeeze default ruby package which has version 1.8.7)
- all rsync-ed files in this procedure are attached

1. Login to the remote machine
[codesyntax lang="bash"]

ssh root@


2. Configure hostname
[codesyntax lang="bash"]

echo "workflow-vm" > /etc/hostname


3. Install all required packages for Redmine installation
[codesyntax lang="bash"]

aptitude install apache2 mysql-server ruby libmysqlclient-dev libmagickcore-dev libmagickwand-dev imagemagick locate less rubygems sudo postfix mercurial cvs subversion darcs git libapache2-mod-passenger libxslt1-dev vim less


4. Configure and test postfix
[codesyntax lang="bash"]

scp /etc/
scp /etc/postfix/

echo "root:" >> /etc/aliases

vim /etc/mailname

vim /etc/postfix/

/etc/init.d/postfix restart

echo "test from new redmine server" | mail -s "test from new redmine server" ""


5. Configuring mysql database
[codesyntax lang="bash"]

mysql -Bsu root -pmysql123 -e "drop database redmine;"
mysql -Bsu root -pmysql123 -e "drop user redmine@localhost;"
mysql -Bsu root -pmysql123 -e "create database redmine character set utf8;"
mysql -Bsu root -pmysql123 -e "create user 'redmine'@'localhost' identified by 'redmine';"
mysql -Bsu root -pmysql123 -e "grant all privileges on redmine.* to 'redmine'@'localhost';"
mysql -Bsu root -pmysql123 -e "flush privileges;"
# dump mysql database from production environment and importing it to our machine
# maybe it is a good idea to use dbredmine as mysql server
# anyway for now we are going to use localhost as mysql server
mysqldump -hdbredmine redmine_default > ~/redmine_production.sql
mysql -u redmine -predmine redmine < ~/redmine_production.sql


6. Configure gems
[codesyntax lang="bash"]

echo "gem: --no-rdoc --no-ri" > ~/.gemrc


7. Downloading and installing Redmine
[codesyntax lang="bash"]

wget -c
tar xfz redmine-1.4.4.tar.gz
mv redmine-1.4.4 /usr/share/redmine
cd /usr/share/
chown -R root:root /usr/share/redmine
chown www-data /usr/share/redmine/config/environment.rb
ln -s /usr/share/redmine/public /var/www/redmine


8. Configuring Redmine
[codesyntax lang="bash"]

cp redmine/config/database.yml.example redmine/config/database.yml
vim redmine/config/database.yml
adapter: mysql
database: redmine
host: localhost
username: redmine
password: redmine
encoding: utf8
scp redmine/config/configuration.yml


9. Installing required gems for Redmine
[codesyntax lang="bash"]

gem install bundler
cd redmine
/var/lib/gems/1.8/bin/bundle install --without development test postgresql sqlite
ln -s /var/lib/gems/1.8/bin/rake /usr/bin/


10. Attachments
[codesyntax lang="bash"]

rm -fr /usr/share/redmine/files
mkdir -p /var/lib/redmine/default/files
ln -s /var/lib/redmine/default/files /usr/share/redmine/files
# copying attachments from production environment
rsync -avz --stats --progress root@*  /usr/share/redmine/files


11. Fixing permissions
[codesyntax lang="bash"]

mkdir public/plugin_assets
chown -R www-data:www-data files log tmp public/plugin_assets
chmod -R 755 files log tmp public/plugin_assets


12. Configuring Apache web server

[codesyntax lang="bash"]

vim /etc/apache2/sites-available/redmine
<VirtualHost *:443>
        ServerAlias workflow
        DocumentRoot /var/www

        SSLEngine on
        SSLCertificateFile /etc/apache2/ssl/
        SSLCertificateKeyFile /etc/apache2/ssl/

LogLevel warn
ErrorLog /var/log/apache2/redmine_error
CustomLog /var/log/apache2/redmine_access combined
<Directory /var/www/redmine>
Options Indexes FollowSymLinks MultiViews
AllowOverride None
Order allow,deny
allow from all
RailsBaseURI /redmine
PassengerResolveSymlinksInDocumentRoot on


[codesyntax lang="bash"]

vim /etc/apache2/ports.conf
:%s/NameVirtualHost \*:80/NameVirtualHost \*:443
:%s/Listen 80/#Listen 80


[codesyntax lang="bash"]

rsync -avz --stats --progress /etc/apache2

mv /etc/apache2/sites-enabled/000-default /tmp

a2ensite redmine
a2enmod passenger
a2enmod ssl


13. Installing and migrating Redmine plugins
[codesyntax lang="bash"]

 cd vendor/plugins


13.1. Question plugin
[codesyntax lang="bash"]

rsync -avz --stats --progress root@ /usr/share/redmine/vendor/plugins/
rsync -avz --stats --progress root@* /usr/share/redmine/app/views/mailer/
mv /usr/share/redmine/app/views/mailer/_issue_text_html.rhtml /usr/share/redmine/app/views/mailer/_issue_text_html.erb
mv /usr/share/redmine/app/views/mailer/_issue_text_plain.rhtml /usr/share/redmine/app/views/mailer/_issue_text_plain.erb


13.2. Redmine Status plugin
[codesyntax lang="bash"]

 rsync -avz --stats --progress /usr/share/redmine/vendor/plugins/


13.3. Redmine Stuff to do plugin
[codesyntax lang="bash"]

rsync -avz --stats --progress /usr/share/redmine/vendor/plugins/
rsync -avz --stats --progress /usr/share/redmine/lib/


14. Fixing permissions for log file
[codesyntax lang="bash"]

cd /usr/share/redmine
chown www-data:www-data log/production.log


15. Final steps to get Redmine working
[codesyntax lang="bash"]

rake generate_session_store
rake db:migrate RAILS_ENV=production
rake db:migrate_plugins RAILS_ENV=production
rake tmp:cache:clear
rake tmp:sessions:clear


16. Restart Apache web server
[codesyntax lang="bash"]

 /etc/init.d/apache2 restart


question plugin: question_plugin.tar.gz
redmine status plugin: redmine_status.tar.gz
stuff to do plugin: stuff_to_do_plugin.tar.gz

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