diff --git a/middleman-core/features/directory_index.feature b/middleman-core/features/directory_index.feature
index 99dbe60e..c1b8f2ef 100644
--- a/middleman-core/features/directory_index.feature
+++ b/middleman-core/features/directory_index.feature
@@ -27,12 +27,12 @@ Feature: Directory Index
     And the file "regular/index.html" should contain "Regular"
     And the file "evil spaces/index.html" should contain "Spaces"
 
-    
+
   Scenario: Preview normal file
     Given the Server is running at "indexable-app"
     When I go to "/needs_index/"
     Then I should see "Indexable"
-    
+
   Scenario: Preview normal file with spaces in filename
     Given the Server is running at "indexable-app"
     When I go to "/evil%20spaces/"
@@ -42,7 +42,7 @@ Feature: Directory Index
     Given the Server is running at "indexable-app"
     When I go to "/a_folder/needs_index/"
     Then I should see "Indexable"
-    
+
   Scenario: Preview ignored file
     Given the Server is running at "indexable-app"
     When I go to "/leave_me_alone/"
@@ -69,14 +69,13 @@ Feature: Directory Index
     And the Server is running at "indexable-app"
     When I go to "/link_to/"
     Then I should see 'link_to: <a href="/needs_index/">Needs Index</a>'
-    Then I should see 'explicit_link_to: <a href="/needs_index/index.html">Explicit</a>'
+    Then I should see 'explicit_link_to: <a href="/needs_index/">Explicit</a>'
     Then I should see 'unknown_link_to: <a href="/unknown.html">Unknown</a>'
     Then I should see 'relative_link_to: <a href="/needs_index/">Relative</a>'
     Then I should see 'link_to_with_spaces: <a href="/evil%20spaces/">Spaces</a>'
     When I go to "/link_to/sub/"
     Then I should see 'link_to: <a href="/needs_index/">Needs Index</a>'
-    Then I should see 'explicit_link_to: <a href="/needs_index/index.html">Explicit</a>'
+    Then I should see 'explicit_link_to: <a href="/needs_index/">Explicit</a>'
     Then I should see 'unknown_link_to: <a href="/unknown.html">Unknown</a>'
     Then I should see 'relative_link_to: <a href="/needs_index/">Relative</a>'
     Then I should see 'link_to_with_spaces: <a href="/evil%20spaces/">Spaces</a>'
-
diff --git a/middleman-core/lib/middleman-core/util.rb b/middleman-core/lib/middleman-core/util.rb
index 5ce84523..eabd3e8e 100644
--- a/middleman-core/lib/middleman-core/util.rb
+++ b/middleman-core/lib/middleman-core/util.rb
@@ -247,7 +247,16 @@ module Middleman
         current_source_dir = Pathname('/' + this_resource.path).dirname
         url_path = current_source_dir.join(url_path) if url_path.relative?
         resource = app.sitemap.find_resource_by_path(url_path.to_s)
-        resource_url = resource.url if resource
+        if resource
+          resource_url = resource.url
+        else
+          # Try to find a resource relative to destination paths
+          url_path = Pathname(uri.path)
+          current_source_dir = Pathname('/' + this_resource.destination_path).dirname
+          url_path = current_source_dir.join(url_path) if url_path.relative?
+          resource = app.sitemap.find_resource_by_destination_path(url_path.to_s)
+          resource_url = resource.url if resource
+        end
       elsif options[:find_resource] && uri.path
         resource = app.sitemap.find_resource_by_path(uri.path)
         resource_url = resource.url if resource