diff --git a/actionpack/lib/action_dispatch/routing/route_set.rb b/actionpack/lib/action_dispatch/routing/route_set.rb
index 3ae9f92c0b..fca663b2a3 100644
--- a/actionpack/lib/action_dispatch/routing/route_set.rb
+++ b/actionpack/lib/action_dispatch/routing/route_set.rb
@@ -184,12 +184,27 @@ module ActionDispatch
             def optimized_helper(args)
               path = @string_route.dup
               klass = Journey::Router::Utils
+              parameterized_args = args.map(&:to_param)
+              missing_keys = []
 
-              @path_parts.zip(args) do |part, arg|
+              parameterized_args.each_with_index do |arg, index|
+                if arg.nil? || arg.empty?
+                  missing_keys << @path_parts[index]
+                end
+              end
+
+              unless missing_keys.empty?
+                message = "No route matches #{Hash[@path_parts.zip(args)].inspect}"
+                message << " missing required keys: #{missing_keys.inspect}"
+
+                raise ActionController::UrlGenerationError, message
+              end
+
+              @path_parts.zip(parameterized_args) do |part, arg|
                 # Replace each route parameter
                 # e.g. :id for regular parameter or *path for globbing
                 # with ruby string interpolation code
-                path.gsub!(/(\*|:)#{part}/, klass.escape_fragment(arg.to_param))
+                path.gsub!(/(\*|:)#{part}/, klass.escape_fragment(arg))
               end
               path
             end
diff --git a/actionpack/test/routing/helper_test.rb b/actionpack/test/routing/helper_test.rb
index a5588d95fa..0028aaa629 100644
--- a/actionpack/test/routing/helper_test.rb
+++ b/actionpack/test/routing/helper_test.rb
@@ -22,7 +22,7 @@ module ActionDispatch
         x = Class.new {
           include rs.url_helpers
         }
-        assert_raises ActionController::RoutingError do
+        assert_raises ActionController::UrlGenerationError do
           x.new.pond_duck_path Duck.new
         end
       end