Many online services and products require users to point and interact with user interface elements. For individuals who experience variable pointing ability due to physical impairments, environmental issues or age, using an input device (e.g., a computer mouse) to select elements on a website can be difficult. Adaptive user interfaces dynamically change their functionality in response to user behavior. They can support individuals with variable pointing abilities by 1) adapting dynamically to make element selection easier when a user is experiencing pointing difficulties, and 2) informing users about these pointing errors. While adaptive interfaces are increasingly prevalent on the Web, little is known about the preferences and expectations of users with variable pointing abilities and how to design systems that dynamically support them given these preferences. We conducted an investigation with 27 individuals who intermittently experience pointing problems to inform the design of an adaptive interface for web navigation. We used a functional high-fidelity prototype as a probe to gather information about user preferences and expectations. Our participants expected the system to recognize and integrate their preferences for how pointing tasks were carried out, preferred to receive information about system functionality and wanted to be in control of the interaction. We used findings from the study to inform the design of an adaptive Web navigation interface, PINATA that tracks user pointing performance over time and provides dynamic notifications and assistance tailored to their specifications. Our work contributes to a better understanding of users? preferences and expectations of the design of an adaptive pointing system.