A simple guardfile for a compass project, that updates each directory within the `sass_dir` with an index file called `_all.scss` in which there are imports for every other scss file in that folder making importation of all files simple. update sass_dir per project.

sass_index_guardfile.rb

# Example Directory structure
# /path/to/project
# |───scss
# |   |───library
# |   |   |───_all.scss         <------- creates/updates this file
# |   |   |───_typography.scss
# |   |   |───_structure.scss
# |   |   └───_responsive.scss
# |   |───modules
# |   |   |───_all.scss         <------- and this file
# |   |   |───_lightbox.scss
# |   |   |───_navigation.scss
# |   |   |───_user-interface.scss
# |   |   └───_buttons.scss
# |   |───_config.scss
# |   |───_normalize.scss 
# |   |───_base.scss 
# |   |───_structure.scss 
# |   └───_typography.scss 
# |───config.rb
# └───Guardfile

guard('compass') { watch %r{(.*)\.s[ac]ss$} }

# Needed for FileList Module in IndexUpdater
require 'rake'

# Mirror config.rb
SASS_DIR = 'scss'
SYNTAX   = :scss

class SassIndexUpdater < Struct.new(:sass_dir, :preferred_syntax)
  def run
    Dir[ File.join(sass_dir,'*') ].map do |f|
      update_dir(f) if File.directory?(f)
    end
  end
  def update_dir(dir)
    index = FileList[ File.join(dir, "*.#{preferred_syntax.to_s}") ]
    index = index.exclude(/\_all\.#{preferred_syntax.to_s}$/)
    imports = index.map do |f|
      "@import \"#{File.basename(f, ".#{preferred_syntax.to_s}").gsub(/^\_/,'')}\";"
    end
    File.open( File.join(dir, "_all.#{preferred_syntax.to_s}"), 'w' ) do |f|
      f.puts imports
    end
  end
end

# Update directories index sass file
guard 'shell' do
  watch %r{(.*)\.s[ac]ss$} do |m|
    SassIndexUpdater.new( SASS_DIR, SYNTAX ).run
  end
end