diff --git a/lib/sass_spec/directory.rb b/lib/sass_spec/directory.rb
index 878f7a5387..9cfdc307fe 100644
--- a/lib/sass_spec/directory.rb
+++ b/lib/sass_spec/directory.rb
@@ -164,9 +164,14 @@ def delete_dir!
   def with_real_files
     return yield unless @archive
 
+    files = @archive.entries.select {|entry| entry.is_a?(HRX::File)}.to_a
+    if parent.hrx? && files.any? {|file| _reaches_out?(file)}
+      return parent.with_real_files {yield}
+    end
+
     outermost_new_dir = SassSpec::Util.each_directory(@path).find {|dir| !Dir.exist?(dir)}
 
-    @archive.entries.select {|entry| entry.is_a?(HRX::File)}.each do |file|
+    files.each do |file|
       path = File.join(@path, file.path)
       FileUtils.mkdir_p(File.dirname(path))
       File.write(path, file.content)
@@ -195,6 +200,13 @@ def to_s
 
   private
 
+  # Returns whether `file` contains enough `../` references to reach outside
+  # this directory.
+  def _reaches_out?(file)
+    depth = file.path.count("/")
+    file.content.scan(%r{(?:\.\./)+}).any? {|match| match.count("/") > depth}
+  end
+
   # Writes `@parent_archive` to disk.
   def _write!
     @parent_archive.write!(@parent_archive_path)