I installed ruby 1.9.2 via RVM as well as the webby and capistrano gems. Webby doesn't work with 1.9.2 so I backed up to ruby 1.8.7 via RVM set it to default and webby is better.
When running cap deploy on this previously functioning site (for someone else) I get the following:
ryan@ruby1:~/projects/cincinnati-agile-conference$ cap deploy /home/ryan/.rvm/rubies/ruby-1.8.7-p334/lib/ruby/site_ruby/1.8/rubygems/custom_require.rb:29:in
gem_original_require': no such file to load -- railsless-deploy (LoadError) from /home/ryan/.rvm/rubies/ruby-1.8.7-p334/lib/ruby/site_ruby/1.8/rubygems/custom_require.rb:29:in
require' from /home/ryan/.rvm/gems/ruby-1.8.7-p334/gems/capistrano-2.5.19/lib/capistrano/configuration/loading.rb:152:inrequire' from Capfile:5:in
load' from /home/ryan/.rvm/gems/ruby-1.8.7-p334/gems/capistrano-2.5.19/lib/capistrano/configuration/loading.rb:172:inload_from_file' from /home/ryan/.rvm/gems/ruby-1.8.7-p334/gems/capistrano-2.5.19/lib/capistrano/configuration/loading.rb:89:in
load' from /home/ryan/.rvm/gems/ruby-1.8.7-p334/gems/capistrano-2.5.19/lib/capistrano/configuration/loading.rb:86:inload' from /home/ryan/.rvm/gems/ruby-1.8.7-p334/gems/capistrano-2.5.19/lib/capistrano/configuration/loading.rb:86:in
each' from /home/ryan/.rvm/gems/ruby-1.8.7-p334/gems/capistrano-2.5.19/lib/capistrano/configuration/loading.rb:86:inload' from /home/ryan/.rvm/gems/ruby-1.8.7-p334/gems/capistrano-2.5.19/lib/capistrano/cli/execute.rb:65:in
load_recipes' from /home/ryan/.rvm/gems/ruby-1.8.7-p334/gems/capistrano-2.5.19/lib/capistrano/cli/execute.rb:65:ineach' from /home/ryan/.rvm/gems/ruby-1.8.7-p334/gems/capistrano-2.5.19/lib/capistrano/cli/execute.rb:65:in
load_recipes' from /home/ryan/.rvm/gems/ruby-1.8.7-p334/gems/capistrano-2.5.19/lib/capistrano/cli/execute.rb:31:inexecute!' from /home/ryan/.rvm/gems/ruby-1.8.7-p334/gems/capistrano-2.5.19/lib/capistrano/cli/execute.rb:14:in
execute' from /home/ryan/.rvm/gems/ruby-1.8.7-p334/gems/capistrano-2.5.19/bin/cap:4 from /home/ryan/.rvm/gems/ruby-1.8.7-p334/bin/cap:19:in `load' from /home/ryan/.rvm/gems/ruby-1.8.7-p334/bin/cap:19
Google-fu leads me to suggestions not to use ruby packages, but I used RVM.
When you fell back to 1.8.7, did you install the railsless-deploy gem?