I know this is probably an easy question but I am stumped here.
The application I am working on houses assets like so:
app --assets ----fonts ----image
It's possible if you manually add all paths underneath app/assets/images to the Rails asset paths in your application.rb:
app/assets/images
application.rb
Dir.glob("#{Rails.root}/app/assets/images/**/").each do |path| config.assets.paths << path end