diff --git a/django/contrib/staticfiles/storage.py b/django/contrib/staticfiles/storage.py
index a804c5626c..cf0c4a0e3a 100644
--- a/django/contrib/staticfiles/storage.py
+++ b/django/contrib/staticfiles/storage.py
@@ -113,13 +113,22 @@ class CachedFilesMixin(object):
                 return matched
             name_parts = name.split('/')
             # Using posix normpath here to remove duplicates
-            result = url_parts = posixpath.normpath(url).split('/')
-            level = url.count('..')
-            if level:
-                result = name_parts[:-level - 1] + url_parts[level:]
-            elif name_parts[:-1]:
-                result = name_parts[:-1] + url_parts[-1:]
-            joined_result = '/'.join(result)
+            url = posixpath.normpath(url)
+            url_parts = url.split('/')
+            parent_level, sub_level = url.count('..'), url.count('/')
+            if url.startswith('/'):
+                sub_level -= 1
+                url_parts = url_parts[1:]
+            if parent_level or not url.startswith('/'):
+                start, end = parent_level + 1, parent_level
+            else:
+                if sub_level:
+                    if sub_level == 1:
+                        parent_level -= 1
+                    start, end = parent_level, sub_level - 1
+                else:
+                    start, end = 1, sub_level - 1
+            joined_result = '/'.join(name_parts[:-start] + url_parts[end:])
             hashed_url = self.url(joined_result, force=True)
             # Return the hashed and normalized version to the file
             return 'url("%s")' % hashed_url
diff --git a/tests/regressiontests/staticfiles_tests/project/documents/cached/css/img/window.png b/tests/regressiontests/staticfiles_tests/project/documents/cached/css/img/window.png
new file mode 100644
index 0000000000..ba48325c0a
Binary files /dev/null and b/tests/regressiontests/staticfiles_tests/project/documents/cached/css/img/window.png differ
diff --git a/tests/regressiontests/staticfiles_tests/project/documents/cached/css/window.css b/tests/regressiontests/staticfiles_tests/project/documents/cached/css/window.css
new file mode 100644
index 0000000000..9fea4e8a5e
--- /dev/null
+++ b/tests/regressiontests/staticfiles_tests/project/documents/cached/css/window.css
@@ -0,0 +1,3 @@
+body {
+    background: #d3d6d8 url("img/window.png");
+}
\ No newline at end of file
diff --git a/tests/regressiontests/staticfiles_tests/project/documents/cached/img/relative.png b/tests/regressiontests/staticfiles_tests/project/documents/cached/img/relative.png
new file mode 100644
index 0000000000..ba48325c0a
Binary files /dev/null and b/tests/regressiontests/staticfiles_tests/project/documents/cached/img/relative.png differ
diff --git a/tests/regressiontests/staticfiles_tests/project/documents/cached/relative.css b/tests/regressiontests/staticfiles_tests/project/documents/cached/relative.css
index 40c4a256aa..afa658dbeb 100644
--- a/tests/regressiontests/staticfiles_tests/project/documents/cached/relative.css
+++ b/tests/regressiontests/staticfiles_tests/project/documents/cached/relative.css
@@ -1,2 +1,5 @@
 @import url("../cached/styles.css");
-@import url("absolute.css");
\ No newline at end of file
+@import url("absolute.css");
+body {
+    background: #d3d6d8 url(img/relative.png);
+}
\ No newline at end of file
diff --git a/tests/regressiontests/staticfiles_tests/project/documents/cached/styles.css b/tests/regressiontests/staticfiles_tests/project/documents/cached/styles.css
index 84936d1dcb..ca28fc35cd 100644
--- a/tests/regressiontests/staticfiles_tests/project/documents/cached/styles.css
+++ b/tests/regressiontests/staticfiles_tests/project/documents/cached/styles.css
@@ -1 +1 @@
-@import url("cached/other.css");
\ No newline at end of file
+@import url("other.css");
\ No newline at end of file
diff --git a/tests/regressiontests/staticfiles_tests/tests.py b/tests/regressiontests/staticfiles_tests/tests.py
index 40569484df..8a179141b9 100644
--- a/tests/regressiontests/staticfiles_tests/tests.py
+++ b/tests/regressiontests/staticfiles_tests/tests.py
@@ -300,11 +300,11 @@ class TestCollectionCachedStorage(BaseCollectionTestCase,
             """, "/static/test/file.dad0999e4f8f.txt")
         self.assertTemplateRenders("""
             {% load static from staticfiles %}{% static "cached/styles.css" %}
-            """, "/static/cached/styles.5653c259030b.css")
+            """, "/static/cached/styles.93b1147e8552.css")
 
     def test_template_tag_simple_content(self):
         relpath = self.cached_file_path("cached/styles.css")
-        self.assertEqual(relpath, "cached/styles.5653c259030b.css")
+        self.assertEqual(relpath, "cached/styles.93b1147e8552.css")
         with storage.staticfiles_storage.open(relpath) as relfile:
             content = relfile.read()
             self.assertFalse("cached/other.css" in content, content)
@@ -316,7 +316,7 @@ class TestCollectionCachedStorage(BaseCollectionTestCase,
         with storage.staticfiles_storage.open(relpath) as relfile:
             content = relfile.read()
             self.assertFalse("/static/cached/styles.css" in content)
-            self.assertTrue("/static/cached/styles.5653c259030b.css" in content)
+            self.assertTrue("/static/cached/styles.93b1147e8552.css" in content)
 
     def test_template_tag_denorm(self):
         relpath = self.cached_file_path("cached/denorm.css")
@@ -324,16 +324,26 @@ class TestCollectionCachedStorage(BaseCollectionTestCase,
         with storage.staticfiles_storage.open(relpath) as relfile:
             content = relfile.read()
             self.assertFalse("..//cached///styles.css" in content)
-            self.assertTrue("/static/cached/styles.5653c259030b.css" in content)
+            self.assertTrue("/static/cached/styles.93b1147e8552.css" in content)
 
     def test_template_tag_relative(self):
         relpath = self.cached_file_path("cached/relative.css")
-        self.assertEqual(relpath, "cached/relative.298ff891a8d4.css")
+        self.assertEqual(relpath, "cached/relative.8dffb45d91f5.css")
         with storage.staticfiles_storage.open(relpath) as relfile:
             content = relfile.read()
             self.assertFalse("../cached/styles.css" in content)
             self.assertFalse('@import "styles.css"' in content)
-            self.assertTrue("/static/cached/styles.5653c259030b.css" in content)
+            self.assertTrue("/static/cached/styles.93b1147e8552.css" in content)
+            self.assertFalse("url(img/relative.png)" in content)
+            self.assertTrue("/static/cached/img/relative.acae32e4532b.png" in content)
+
+    def test_template_tag_deep_relative(self):
+        relpath = self.cached_file_path("cached/css/window.css")
+        self.assertEqual(relpath, "cached/css/window.9db38d5169f3.css")
+        with storage.staticfiles_storage.open(relpath) as relfile:
+            content = relfile.read()
+            self.assertFalse('url(img/window.png)' in content)
+            self.assertTrue('url("/static/cached/css/img/window.acae32e4532b.png")' in content)
 
     def test_template_tag_url(self):
         relpath = self.cached_file_path("cached/url.css")