diff --git a/lib/jekyll/url.rb b/lib/jekyll/url.rb
index aeb2ac0d..d57352c4 100644
--- a/lib/jekyll/url.rb
+++ b/lib/jekyll/url.rb
@@ -144,7 +144,13 @@ module Jekyll
       #   pct-encoded   = "%" HEXDIG HEXDIG
       #   sub-delims    = "!" / "$" / "&" / "'" / "(" / ")"
       #                 / "*" / "+" / "," / ";" / "="
-      Addressable::URI.encode(path).encode("utf-8").sub("#", "%23")
+      #
+      # `Addressable::URI::CharacterClassesRegexps::PATH` is used to encode
+      # non-alphanumeric characters such as "[", "]", etc.
+      Addressable::URI.encode_component(
+        path,
+        Addressable::URI::CharacterClassesRegexps::PATH
+      ).encode("utf-8").sub("#", "%23")
     end
 
     # Unescapes a URL path segment
diff --git a/test/test_url.rb b/test/test_url.rb
index 859babd4..430789aa 100644
--- a/test/test_url.rb
+++ b/test/test_url.rb
@@ -80,5 +80,16 @@ class TestURL < JekyllUnitTest
         ).to_s
       end
     end
+
+    should "not treat colons in placeholders as uri delimiters" do
+      assert_equal "/foo/foo%20bar:foobar/", URL.new(
+        :template     => "/:x/:y/",
+        :placeholders => { :x => "foo", :y => "foo bar:foobar" }
+      ).to_s
+    end
+
+    should "unescape urls with colons" do
+      assert_equal "/foo/foo bar:foobar/", Jekyll::URL.unescape_path("/foo/foo%20bar:foobar/")
+    end
   end
 end