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EDIT 4, 5 and 6 8 hours in, any more ideas are welcome :) Maybe this bug is already known and solved, but I get the behaviour I described in edit 2&3, when you have this in a .css.erb file in app/assets/stylesheets : li { background-image: url(<%= asset_path "logo_80px_80px.png" %>); } The problem part seems to be the asset_path method call, but .css.scss also breaks it with: li { background-image: url(image-path("logo_80px_80px.png")); } My GemFile is: source 'http://rubygems.org' gem 'rails', '3.1.3' gem 'pg', '0.11.0' gem 'gravatar_image_tag', '1.0.0.pre2' gem 'will_paginate' gem 'rake' gem 'jquery-rails' gem 'nested_form' gem 'acts-as-taggable-on' gem 'sass-rails' group :assets do gem 'coffee-rails', '~> 3.1.0' gem 'uglifier', '>= 1.0.3' end group :development do gem 'rspec-rails', '2.5.0' gem 'annotate', '2.4.0' gem 'faker', '0.3.1' end group :test do gem 'rspec', '2.5.0' gem 'webrat', '0.7.1' gem 'factory_girl_rails', '1.0' end group :production do gem 'therubyracer-heroku' end My Gemfile.lock is: GEM remote: http://rubygems.org/ specs: actionmailer (3.1.3) actionpack (= 3.1.3) mail (~> 2.3.0) actionpack (3.1.3) activemodel (= 3.1.3) activesupport (= 3.1.3) builder (~> 3.0.0) erubis (~> 2.7.0) i18n (~> 0.6) rack (~> 1.3.5) rack-cache (~> 1.1) rack-mount (~> 0.8.2) rack-test (~> 0.6.1) sprockets (~> 2.0.3) activemodel (3.1.3) activesupport (= 3.1.3) builder (~> 3.0.0) i18n (~> 0.6) activerecord (3.1.3) activemodel (= 3.1.3) activesupport (= 3.1.3) arel (~> 2.2.1) tzinfo (~> 0.3.29) activeresource (3.1.3) activemodel (= 3.1.3) activesupport (= 3.1.3) activesupport (3.1

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