This experience report presents context of use research investigating the occupational and technological (e.g. navigational software/hardware) use habits of UBER/LYFT rideshare drivers in the Washington, D.C. metro (~20-mile radius) driving area. This study implemented structured observational context analysis and semi-structured interview to evaluate four (4) primary user interaction domains: 1) User Experience: Knowledge of Hardware, Software, and Technical Language; 2) Task-Specific Use: Effective Use of Device for Navigating and Driving; 3) User Control: Assistive Device and Job Design; 4) Use of Communication: Assistive Dialogue Used by Navigator. Findings were analyzed using quantitative and qualitative methods, with interaction factors evaluated for user impact. Discoveries included: discretionary use of software significantly impacted task performance, driver autonomy, and job satisfaction; error and choice-tolerant navigational devices facilitated occupational satisfaction; and technical language fluency improved device use accuracy and rideshare driver ethos. This study was approved by IRB (974251-1) and all participants provided informed consent.