diff --git a/actionpack/test/dispatch/static_test.rb b/actionpack/test/dispatch/static_test.rb
index e086d99b192fdc779fa77617d6a298223c2bced6..092ca3e20a8de3f96568ab13f1ad760c792e7478 100644
--- a/actionpack/test/dispatch/static_test.rb
+++ b/actionpack/test/dispatch/static_test.rb
@@ -1,5 +1,6 @@
 # encoding: utf-8
 require 'abstract_unit'
+require 'rbconfig'
 
 module StaticTests
   def test_serves_dynamic_content
@@ -35,32 +36,85 @@ def test_served_static_file_with_non_english_filename
     assert_html "means hello in Japanese\n", get("/foo/#{Rack::Utils.escape("こんにちは.html")}")
   end
 
-  def test_serves_static_file_with_encoded_pchar
-    assert_html "/foo/foo!bar.html", get("/foo/foo%21bar.html")
-    assert_html "/foo/foo$bar.html", get("/foo/foo%24bar.html")
-    assert_html "/foo/foo&bar.html", get("/foo/foo%26bar.html")
-    assert_html "/foo/foo'bar.html", get("/foo/foo%27bar.html")
-    assert_html "/foo/foo(bar).html", get("/foo/foo%28bar%29.html")
-    assert_html "/foo/foo*bar.html", get("/foo/foo%2Abar.html")
-    assert_html "/foo/foo+bar.html", get("/foo/foo%2Bbar.html")
-    assert_html "/foo/foo,bar.html", get("/foo/foo%2Cbar.html")
-    assert_html "/foo/foo;bar.html", get("/foo/foo%3Bbar.html")
-    assert_html "/foo/foo:bar.html", get("/foo/foo%3Abar.html")
-    assert_html "/foo/foo@bar.html", get("/foo/foo%40bar.html")
-  end
-
-  def test_serves_static_file_with_unencoded_pchar
-    assert_html "/foo/foo!bar.html", get("/foo/foo!bar.html")
-    assert_html "/foo/foo$bar.html", get("/foo/foo$bar.html")
-    assert_html "/foo/foo&bar.html", get("/foo/foo&bar.html")
-    assert_html "/foo/foo'bar.html", get("/foo/foo'bar.html")
-    assert_html "/foo/foo(bar).html", get("/foo/foo(bar).html")
-    assert_html "/foo/foo*bar.html", get("/foo/foo*bar.html")
-    assert_html "/foo/foo+bar.html", get("/foo/foo+bar.html")
-    assert_html "/foo/foo,bar.html", get("/foo/foo,bar.html")
-    assert_html "/foo/foo;bar.html", get("/foo/foo;bar.html")
-    assert_html "/foo/foo:bar.html", get("/foo/foo:bar.html")
-    assert_html "/foo/foo@bar.html", get("/foo/foo@bar.html")
+
+  def test_serves_static_file_with_exclamation_mark_in_filename
+    with_static_file "/foo/foo!bar.html" do |file|
+      assert_html file, get("/foo/foo%21bar.html")
+      assert_html file, get("/foo/foo!bar.html")
+    end
+  end
+
+  def test_serves_static_file_with_dollar_sign_in_filename
+    with_static_file "/foo/foo$bar.html" do |file|
+      assert_html file, get("/foo/foo%24bar.html")
+      assert_html file, get("/foo/foo$bar.html")
+    end
+  end
+
+  def test_serves_static_file_with_ampersand_in_filename
+    with_static_file "/foo/foo&bar.html" do |file|
+      assert_html file, get("/foo/foo%26bar.html")
+      assert_html file, get("/foo/foo&bar.html")
+    end
+  end
+
+  def test_serves_static_file_with_apostrophe_in_filename
+    with_static_file "/foo/foo'bar.html" do |file|
+      assert_html file, get("/foo/foo%27bar.html")
+      assert_html file, get("/foo/foo'bar.html")
+    end
+  end
+
+  def test_serves_static_file_with_parentheses_in_filename
+    with_static_file "/foo/foo(bar).html" do |file|
+      assert_html file, get("/foo/foo%28bar%29.html")
+      assert_html file, get("/foo/foo(bar).html")
+    end
+  end
+
+  def test_serves_static_file_with_plus_sign_in_filename
+    with_static_file "/foo/foo+bar.html" do |file|
+      assert_html file, get("/foo/foo%2Bbar.html")
+      assert_html file, get("/foo/foo+bar.html")
+    end
+  end
+
+  def test_serves_static_file_with_comma_in_filename
+    with_static_file "/foo/foo,bar.html" do |file|
+      assert_html file, get("/foo/foo%2Cbar.html")
+      assert_html file, get("/foo/foo,bar.html")
+    end
+  end
+
+  def test_serves_static_file_with_semi_colon_in_filename
+    with_static_file "/foo/foo;bar.html" do |file|
+      assert_html file, get("/foo/foo%3Bbar.html")
+      assert_html file, get("/foo/foo;bar.html")
+    end
+  end
+
+  def test_serves_static_file_with_at_symbol_in_filename
+    with_static_file "/foo/foo@bar.html" do |file|
+      assert_html file, get("/foo/foo%40bar.html")
+      assert_html file, get("/foo/foo@bar.html")
+    end
+  end
+
+  # Windows doesn't allow \ / : * ? " < > | in filenames
+  unless RbConfig::CONFIG['host_os'] =~ /mswin|mingw/
+    def test_serves_static_file_with_colon
+      with_static_file "/foo/foo:bar.html" do |file|
+        assert_html file, get("/foo/foo%3Abar.html")
+        assert_html file, get("/foo/foo:bar.html")
+      end
+    end
+
+    def test_serves_static_file_with_asterisk
+      with_static_file "/foo/foo*bar.html" do |file|
+        assert_html file, get("/foo/foo%2Abar.html")
+        assert_html file, get("/foo/foo*bar.html")
+      end
+    end
   end
 
   private
@@ -73,6 +127,14 @@ def assert_html(body, response)
     def get(path)
       Rack::MockRequest.new(@app).request("GET", path)
     end
+
+    def with_static_file(file)
+      path = "#{FIXTURE_LOAD_PATH}/public" + file
+      File.open(path, "wb+") { |f| f.write(file) }
+      yield file
+    ensure
+      File.delete(path)
+    end
 end
 
 class StaticTest < ActiveSupport::TestCase
diff --git a/actionpack/test/fixtures/public/foo/foo!bar.html b/actionpack/test/fixtures/public/foo/foo!bar.html
deleted file mode 100644
index 2928f2717fafe77e7282f47df7eb197d7e7959d7..0000000000000000000000000000000000000000
--- a/actionpack/test/fixtures/public/foo/foo!bar.html
+++ /dev/null
@@ -1 +0,0 @@
-/foo/foo!bar.html
\ No newline at end of file
diff --git a/actionpack/test/fixtures/public/foo/foo$bar.html b/actionpack/test/fixtures/public/foo/foo$bar.html
deleted file mode 100644
index 4f837df01da8579a588fdda20783f60d3e4997cb..0000000000000000000000000000000000000000
--- a/actionpack/test/fixtures/public/foo/foo$bar.html
+++ /dev/null
@@ -1 +0,0 @@
-/foo/foo$bar.html
\ No newline at end of file
diff --git a/actionpack/test/fixtures/public/foo/foo&bar.html b/actionpack/test/fixtures/public/foo/foo&bar.html
deleted file mode 100644
index c194e8de87b84177e4f45b98ef6bd26dd7b9fdcd..0000000000000000000000000000000000000000
--- a/actionpack/test/fixtures/public/foo/foo&bar.html
+++ /dev/null
@@ -1 +0,0 @@
-/foo/foo&bar.html
\ No newline at end of file
diff --git a/actionpack/test/fixtures/public/foo/foo'bar.html b/actionpack/test/fixtures/public/foo/foo'bar.html
deleted file mode 100644
index 25c3275736bc77844a845960fc73e3f8710fb975..0000000000000000000000000000000000000000
--- a/actionpack/test/fixtures/public/foo/foo'bar.html
+++ /dev/null
@@ -1 +0,0 @@
-/foo/foo'bar.html
\ No newline at end of file
diff --git a/actionpack/test/fixtures/public/foo/foo(bar).html b/actionpack/test/fixtures/public/foo/foo(bar).html
deleted file mode 100644
index 94fa4cb944cf4bc7a501b6f50c0323f2cbd6acb5..0000000000000000000000000000000000000000
--- a/actionpack/test/fixtures/public/foo/foo(bar).html
+++ /dev/null
@@ -1 +0,0 @@
-/foo/foo(bar).html
\ No newline at end of file
diff --git a/actionpack/test/fixtures/public/foo/foo*bar.html b/actionpack/test/fixtures/public/foo/foo*bar.html
deleted file mode 100644
index 79d5194c8d94fc79ffad020aa97c0df6d86a327f..0000000000000000000000000000000000000000
--- a/actionpack/test/fixtures/public/foo/foo*bar.html
+++ /dev/null
@@ -1 +0,0 @@
-/foo/foo*bar.html
\ No newline at end of file
diff --git a/actionpack/test/fixtures/public/foo/foo+bar.html b/actionpack/test/fixtures/public/foo/foo+bar.html
deleted file mode 100644
index 0fdc2ecabcfed3f75a1554427104b99af0bb6ced..0000000000000000000000000000000000000000
--- a/actionpack/test/fixtures/public/foo/foo+bar.html
+++ /dev/null
@@ -1 +0,0 @@
-/foo/foo+bar.html
\ No newline at end of file
diff --git a/actionpack/test/fixtures/public/foo/foo,bar.html b/actionpack/test/fixtures/public/foo/foo,bar.html
deleted file mode 100644
index f040fce197f4502077c0ee19ada8ee8c22ac4a3d..0000000000000000000000000000000000000000
--- a/actionpack/test/fixtures/public/foo/foo,bar.html
+++ /dev/null
@@ -1 +0,0 @@
-/foo/foo,bar.html
\ No newline at end of file
diff --git a/actionpack/test/fixtures/public/foo/foo:bar.html b/actionpack/test/fixtures/public/foo/foo:bar.html
deleted file mode 100644
index 7900a2642bc493f3fea385d9b424660fdf1bce3c..0000000000000000000000000000000000000000
--- a/actionpack/test/fixtures/public/foo/foo:bar.html
+++ /dev/null
@@ -1 +0,0 @@
-/foo/foo:bar.html
\ No newline at end of file
diff --git a/actionpack/test/fixtures/public/foo/foo;bar.html b/actionpack/test/fixtures/public/foo/foo;bar.html
deleted file mode 100644
index 224837695476f9d618048aa1609d99b1e3cdf04c..0000000000000000000000000000000000000000
--- a/actionpack/test/fixtures/public/foo/foo;bar.html
+++ /dev/null
@@ -1 +0,0 @@
-/foo/foo;bar.html
\ No newline at end of file
diff --git a/actionpack/test/fixtures/public/foo/foo=bar.html b/actionpack/test/fixtures/public/foo/foo=bar.html
deleted file mode 100644
index 206f69e286e26c93508340f8d489f3667dc0d772..0000000000000000000000000000000000000000
--- a/actionpack/test/fixtures/public/foo/foo=bar.html
+++ /dev/null
@@ -1 +0,0 @@
-/foo/foo=bar.html
\ No newline at end of file
diff --git a/actionpack/test/fixtures/public/foo/foo@bar.html b/actionpack/test/fixtures/public/foo/foo@bar.html
deleted file mode 100644
index 4e8e90f9b8e7845df08ad3e785c47eff0a380206..0000000000000000000000000000000000000000
--- a/actionpack/test/fixtures/public/foo/foo@bar.html
+++ /dev/null
@@ -1 +0,0 @@
-/foo/foo@bar.html
\ No newline at end of file