Pest abundance on urban trees often increases with surrounding impervious surface. Gloomy scale (Melanaspis tenebricosa Comstock; Hemiptera: Diaspididae), a pest of red maples (Acer rubrum L.; Sapindales: Sapindaceae) in the southeast United States, reaches injurious levels in cities and reduces tree condition. Here, we use a chronosequence field study in Raleigh, NC, to investigate patterns in gloomy scale densities over time from the nursery to 13 yr after tree planting, with a goal of informing more efficient management of gloomy scale on urban trees. We examine how impervious surfaces affect the progression of infestations and how infestations affect tree condition. We find that gloomy scale densities remain low on trees until at least seven seasons after tree planting, providing a key timepoint for starting scouting efforts. Scouting should focus on tree branches, not tree trunks. Scale density on tree branches increases with impervious surface across the entire studied tree age range and increases faster on individual trees that are planted in areas with high impervious surface cover. There is a lag between the onset of pest infestations and a decline in tree condition, indicating that gloomy scale management should begin prior to a visible decline in tree condition. Our results inform management of gloomy scale in cities.