diff --git a/src/extend.cpp b/src/extend.cpp
index 604f6af12b..1c4e5a2c16 100644
--- a/src/extend.cpp
+++ b/src/extend.cpp
@@ -6,6 +6,7 @@
 #include "parser.hpp"
 #include "node.hpp"
 #include "sass_util.hpp"
+#include "remove_placeholders.hpp"
 #include "debug.hpp"
 #include <iostream>
 #include <deque>
@@ -1944,19 +1945,57 @@ namespace Sass {
       }
     }
 
-    for (Complex_Selector* cs : *pNewSelectors) {
-      while (cs) {
-        if (cs->head()) {
-        for (Simple_Selector* ss : *cs->head()) {
-          if (Wrapped_Selector* ws = dynamic_cast<Wrapped_Selector*>(ss)) {
-            if (Selector_List* sl = dynamic_cast<Selector_List*>(ws->selector())) {
-              bool extended = false;
-              ws->selector(extendSelectorList(sl, ctx, subset_map, false, extended));
+    Remove_Placeholders remove_placeholders(ctx);
+    // it seems that we have to remove the place holders early here
+    // normally we do this as the very last step (compare to ruby sass)
+    pNewSelectors = remove_placeholders.remove_placeholders(pNewSelectors);
+
+    // unwrap all wrapped selectors with inner lists
+    for (Complex_Selector* cur : *pNewSelectors) {
+      // process tails
+      while (cur) {
+        // process header
+        if (cur->head()) {
+          // create a copy since we add multiple items if stuff get unwrapped
+          Compound_Selector* cpy_head = SASS_MEMORY_NEW(ctx.mem, Compound_Selector, cur->pstate());
+          for (Simple_Selector* hs : *cur->head()) {
+            if (Wrapped_Selector* ws = dynamic_cast<Wrapped_Selector*>(hs)) {
+              if (Selector_List* sl = dynamic_cast<Selector_List*>(ws->selector())) {
+                // special case for ruby ass
+                if (sl->empty()) {
+                  // this seems inconsistent but it is how ruby sass seems to remove parentheses
+                  *cpy_head << SASS_MEMORY_NEW(ctx.mem, Type_Selector, hs->pstate(), ws->name());
+                }
+                // has wrapped selectors
+                else {
+                  // extend the inner list of wrapped selector
+                  Selector_List* ext_sl = extendSelectorList(sl, ctx, subset_map);
+                  for (size_t i = 0; i < ext_sl->length(); i += 1) {
+                    if (Complex_Selector* ext_cs = ext_sl->at(i)) {
+                      // create clones for wrapped selector and the inner list
+                      Wrapped_Selector* cpy_ws = SASS_MEMORY_NEW(ctx.mem, Wrapped_Selector, *ws);
+                      Selector_List* cpy_ws_sl = SASS_MEMORY_NEW(ctx.mem, Selector_List, sl->pstate());
+                      // remove parent selectors from inner selector
+                      if (ext_cs->first()) *cpy_ws_sl << ext_cs->first();
+                      // assign list to clone
+                      cpy_ws->selector(cpy_ws_sl);
+                      // append the clone
+                      *cpy_head << cpy_ws;
+                    }
+                  }
+                }
+              } else {
+                *cpy_head << hs;
+              }
+            } else {
+              *cpy_head << hs;
             }
           }
+          // replace header
+          cur->head(cpy_head);
         }
-        }
-        cs = cs->tail();
+        // process tail
+        cur = cur->tail();
       }
     }
     return pNewSelectors;
diff --git a/src/extend.hpp b/src/extend.hpp
index 7061b3fada..ae86a926f6 100644
--- a/src/extend.hpp
+++ b/src/extend.hpp
@@ -24,6 +24,10 @@ namespace Sass {
   public:
     static Node subweave(Node& one, Node& two, Context& ctx);
     static Selector_List* extendSelectorList(Selector_List* pSelectorList, Context& ctx, ExtensionSubsetMap& subset_map, bool isReplace, bool& extendedSomething);
+    static Selector_List* extendSelectorList(Selector_List* pSelectorList, Context& ctx, ExtensionSubsetMap& subset_map, bool isReplace = false) {
+      bool extendedSomething = false;
+      return extendSelectorList(pSelectorList, ctx, subset_map, isReplace, extendedSomething);
+    }
     Extend(Context&, ExtensionSubsetMap&);
     ~Extend() { }
 
diff --git a/src/functions.cpp b/src/functions.cpp
index 8078255611..0de627b88c 100644
--- a/src/functions.cpp
+++ b/src/functions.cpp
@@ -1889,8 +1889,7 @@ namespace Sass {
       ExtensionSubsetMap subset_map;
       extender->populate_extends(extendee, ctx, subset_map);
 
-      bool extendedSomething;
-      Selector_List* result = Extend::extendSelectorList(selector, ctx, subset_map, false, extendedSomething);
+      Selector_List* result = Extend::extendSelectorList(selector, ctx, subset_map, false);
 
       Listize listize(ctx.mem);
       return result->perform(&listize);
@@ -1906,8 +1905,7 @@ namespace Sass {
       ExtensionSubsetMap subset_map;
       replacement->populate_extends(original, ctx, subset_map);
 
-      bool extendedSomething;
-      Selector_List* result = Extend::extendSelectorList(selector, ctx, subset_map, true, extendedSomething);
+      Selector_List* result = Extend::extendSelectorList(selector, ctx, subset_map, true);
 
       Listize listize(ctx.mem);
       return result->perform(&listize);
diff --git a/src/remove_placeholders.hpp b/src/remove_placeholders.hpp
index 762dd2344c..ed583cddba 100644
--- a/src/remove_placeholders.hpp
+++ b/src/remove_placeholders.hpp
@@ -17,7 +17,7 @@ namespace Sass {
 
         void fallback_impl(AST_Node* n) {}
 
-    private:
+    public:
       Selector_List* remove_placeholders(Selector_List*);
 
     public: