diff --git a/lib/yard/core_ext/file.rb b/lib/yard/core_ext/file.rb
index 938652081..20e98538e 100644
--- a/lib/yard/core_ext/file.rb
+++ b/lib/yard/core_ext/file.rb
@@ -34,7 +34,7 @@ def self.cleanpath(path)
     path = path.split(SEPARATOR)
     path = path.inject([]) do |acc, comp|
       next acc if comp == RELATIVE_SAMEDIR
-      if comp == RELATIVE_PARENTDIR && acc.size > 0
+      if comp == RELATIVE_PARENTDIR && acc.size > 0 && acc.last != RELATIVE_PARENTDIR
         acc.pop
         next acc
       end
diff --git a/spec/core_ext/file_spec.rb b/spec/core_ext/file_spec.rb
index 153e816c6..7bba3d2dd 100644
--- a/spec/core_ext/file_spec.rb
+++ b/spec/core_ext/file_spec.rb
@@ -41,9 +41,13 @@
       File.cleanpath('A/B/C/D/..').should == "A/B/C"
     end
     
-    it "should not pass the initial directory" do
+    it "should pass the initial directory" do
       File.cleanpath('C/../../D').should == "../D"
     end
+    
+    it "should not remove multiple '../' at the beginning" do
+      File.cleanpath('../../A/B').should == '../../A/B'
+    end
   end
   
   describe '.open!' do