I recommend to go straight to 2.1.5+ without intermediate steps. Otherwhise you burden yourself with unnecessary work of encoding problems.
Issues you may encounter:
- 
Set the ruby version within your
.ruby-versionfile to2.1.5 - 
Remove gem
ruby-debugand use e.g.byebug - 
Remove gem
oniguruma - 
Remove gem
fastercsv - 
Replace gem
mysqlwithmysql2 - 
Update gem capistrano
2.12.0to~>2.12when bound forRuby 1.8.7and remove obsolete explicite Gemfile entries fornet-scpandnet-sshif present. - 
Update gem
andand - 
Update gem
parallel_tests(0.8.x to 1.6.x) - 
Downdgrade database_cleaner from
1.4.xto1.2.0 - 
Use new
lambdasyntax: changelambda { |param| code }to->(param) { code } - 
Unbind
gem 'i18n', '~> 0.6.0'and update - 
fix yml erros:
- 
%{count}errors by surrounding with", e.g.: replaceone: %{count} Objektwithone: "%{count} Objekte" - 
date: order: [ :day, :month, :year ]todate: order: - :year - :month - :day 
 - 
 - 
fix
incompatible character encodings: UTF-8 and ASCII-8BITerror by addingEncoding.default_external = Encoding::UTF_8 Encoding.default_internal = Encoding::UTF_8to
environment.rbbeforeAppname::Application.initialize! - 
use
' 'for nbsp helper instead of0xC2.chr + 0xA0.chr - 
TextHelper#truncatechanged signature from(string, int)to(string, length: int) - 
You may update gem
sanitizefrom2.xto4+ - 
In regexes
\wdoes not match umlauts and other special characters. If it is supposed to you can use[[:alnum:]]instead.