The Winding Cisticola is a species of bird in the Cisticolidae family. It is found in Angola, Benin, Botswana, Burkina Faso, Burundi, Cameroon, Central African Republic, Chad, Republic of the Congo, the Democratic Republic of the Congo, Ivory Coast, Eritrea, Ethiopia, Gabon, Gambia, Ghana, Guinea, Guinea-Bissau, Kenya, Malawi, Mali, Mauritania, Mozambique, Namibia, Niger, Nigeria, Rwanda, Senegal, Sierra Leone, Somalia, South Africa, Sudan, Tanzania, Togo, Uganda, Zambia, and Zimbabwe. Its natural habitats are subtropical or tropical seasonally wet or flooded lowland grassland and swamps.