diff --git a/CHANGELOG.md b/CHANGELOG.md
index bdda7ab3be..6ab7a42b35 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -12,6 +12,7 @@
 * [#2370](https://github.com/ruby-grape/grape/pull/2370): Remove route_xyz method_missing deprecation - [@ericproulx](https://github.com/ericproulx).
 * [#2372](https://github.com/ruby-grape/grape/pull/2372): Fix `declared` method for hash params with overlapping names - [@jcagarcia](https://github.com/jcagarcia).
 * [#2373](https://github.com/ruby-grape/grape/pull/2373): Fix markdown files for following 1-line format - [@jcagarcia](https://github.com/jcagarcia).
+* [#2382](https://github.com/ruby-grape/grape/pull/2382): Fix values validator for params wrapped in `with` block - [@numbata](https://github.com/numbata).
 * Your contribution here.
 
 ### 2.0.0 (2023/11/11)
diff --git a/lib/grape/validations/validators/values_validator.rb b/lib/grape/validations/validators/values_validator.rb
index 3be7d609b6..8475ffb822 100644
--- a/lib/grape/validations/validators/values_validator.rb
+++ b/lib/grape/validations/validators/values_validator.rb
@@ -85,7 +85,12 @@ def except_message
         end
 
         def required_for_root_scope?
-          @required && @scope.root?
+          return false unless @required
+
+          scope = @scope
+          scope = scope.parent while scope.lateral?
+
+          scope.root?
         end
 
         def validation_exception(attr_name, message)
diff --git a/spec/grape/validations/validators/values_spec.rb b/spec/grape/validations/validators/values_spec.rb
index d8ef17c95b..5d8daab914 100644
--- a/spec/grape/validations/validators/values_spec.rb
+++ b/spec/grape/validations/validators/values_spec.rb
@@ -261,6 +261,13 @@ def even?(value)
         optional :name, type: String, values: %w[a b], allow_blank: true
       end
       get '/allow_blank'
+
+      params do
+        with(type: String) do
+          requires :type, values: ValuesModel.values
+        end
+      end
+      get 'values_wrapped_by_with_block'
     end
   end
 
@@ -730,4 +737,13 @@ def app
       end
     end
   end
+
+  context 'when wrapped by with block' do
+    it 'rejects an invalid value' do
+      get 'values_wrapped_by_with_block'
+
+      expect(last_response.status).to eq 400
+      expect(last_response.body).to eq({ error: 'type is missing, type does not have a valid value' }.to_json)
+    end
+  end
 end