Lanius ludovicianus (Loggerhead Shrike) is a predatory songbird that has experienced a severe population decline throughout its range since the 1940s, likely driven by a combination of factors, including habitat loss and fragmentation. Occupying larger territories compared to many other passerines, L. ludovicianus requires open habitat with interspersed trees and shrubs for nesting and perching and heterogeneous ground cover that provides hunting opportunities. Despite the general knowledge of L. ludovicianus habitat during breeding and nonbreeding seasons in many parts of its range, factors influencing long-term occupancy dynamics remain poorly understood. We addressed these knowledge gaps by analyzing 10 yr of L. ludovicianus detection data collected from breeding bird point-count surveys at a grassland-sagebrush ecotone in northeastern Wyoming, USA. We quantified L. ludovicianus detection and occupancy probabilities using a dynamic (multi-season) occupancy modeling framework and evaluated how initial occupancy and dynamic parameters (i.e., colonization and local extinction) were influenced by land-cover composition and change using remotely sensed land-cover data. Additionally, we used observer survey data to assess the influence of survey date and cloud cover on detection probability. We found that detection probability was influenced by survey date, while initial occupancy probability was positively associated with fences and presence of trees. Colonization probability increased with increased litter cover, whereas extinction probability was not influenced by land-cover and remained low throughout our study period. These findings highlight the importance of habitat features, such as fences and tree presence in shaping L. ludovicianus occupancy patterns. Further research is needed to understand the relationships between L. ludovicianus occupancy dynamics and demographic processes such as reproduction and survival. Identifying factors that influence occupancy dynamics and associated demographic processes can guide efforts to conserve and sustain L. ludovicianus populations.