You can report specific city streetlight problems via the web
https://iframe.publicstuff.com/#?client_id=1000158&request_type_category_id=5110#picker-top (on left side scroll to bottom and select the Streetlight option)
You can also download the GOCOS! app at https://coloradosprings.gov/page/citizen-request-gocosprings-app and be able to "tag" the location with the app while standing next to the problem streetlight to help the city find the light you are reporting.
You can also call and report a problem via phone (719) 385-5918