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@@ -14,6 +14,12 @@ module Sass
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         :full_exception     => true
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       }
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+      # Whether or not Sass has *ever* checked if the stylesheets need updates
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+      # (in this Ruby instance).
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+      def checked_for_updates
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+        @@checked_for_updates
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+      end
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+
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       # Gets various options for Sass. See README for details.
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       #--
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       # TODO: *DOCUMENT OPTIONS*
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@@ -35,6 +41,7 @@ module Sass
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       def update_stylesheets
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         return if options[:never_update]
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+        @@checked_for_updates = true
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         Dir.glob(File.join(options[:template_location], "**", "*.sass")).entries.each do |file|
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           # Get the relative path to the file with no extension

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@@ -20,7 +20,11 @@ unless defined?(Sass::MERB_LOADED)
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   class MerbHandler # :nodoc:
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     def process_with_sass(request, response)
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-      Sass::Plugin.update_stylesheets if Sass::Plugin.options[:always_update] || Sass::Plugin.options[:always_check]
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+      if !Sass::Plugin.checked_for_updates ||
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+          Sass::Plugin.options[:always_update] || Sass::Plugin.options[:always_check]
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+        Sass::Plugin.update_stylesheets
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+      end
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+
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       process_without_sass(request, response)
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     end
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     alias_method :process_without_sass, :process

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@@ -11,7 +11,11 @@ unless defined?(Sass::RAILS_LOADED)
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     class Base
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       alias_method :sass_old_process, :process
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       def process(*args)
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-        Sass::Plugin.update_stylesheets if Sass::Plugin.options[:always_update] || Sass::Plugin.options[:always_check]
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+        if !Sass::Plugin.checked_for_updates ||
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+            Sass::Plugin.options[:always_update] || Sass::Plugin.options[:always_check]
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+          Sass::Plugin.update_stylesheets
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+        end
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+
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         sass_old_process(*args)
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       end
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     end