Pervasive technologies are used to investigate various phenomena outside the laboratory setting, providing valuable insights into real-world human behavior and interaction with the environment. However, conducting longitudinal field trials in natural settings remains challenging due to factors such as low recruitment success and high dropout rates due to participation burden or data quality issues with wireless sensing in changing environments. This study gathers insights and lessons from 3 real-world longitudinal field studies assessing human behavior and derives factors that impacted their research success. We aim to categorize challenges, observe how they were managed, and offer recommendations for designing and conducting studies involving human participants and pervasive technology in natural settings. We developed a qualitative coding framework to categorize and address the unique challenges encountered in real-life studies related to influential factor identification, stakeholder management, data harvesting and management, and analysis and interpretation. We applied inductive reasoning to identify issues and related mitigation actions in 3 separate field studies carried out between 2018 and 2022. These 3 field studies relied on gathering annotated sensor data. The topics involved stress and environmental assessment in an office and a school, collecting self-reports and wrist device and environmental sensor data from 27 participants for 3.5 to 7 months; work activity recognition at a construction site, collecting observations and wearable sensor data from 15 participants for 3 months; and stress recognition in location-independent knowledge work, collecting self-reports and computer use data from 57 participants for 2 to 5 months. Our key extension for the coding framework used a stakeholder identification method to identify the type and role of the involved stakeholder groups, evaluating the nature and degree of their involvement and influence on the field trial success. Our analysis identifies 17 key lessons related to planning, implementing, and managing a longitudinal, sensor-based field study on human behavior. The findings highlight the importance of recognizing different stakeholder groups, including those not directly involved but whose areas of responsibility are impacted by the study and therefore have the power to influence it. In general, customizing communication strategies to engage stakeholders on their terms and addressing their concerns and expectations is essential, while planning for dropouts, offering incentives for participants, conducting field tests to identify problems, and using tools for quality assurance are relevant for successful outcomes. Our findings suggest that field trial implementation should include additional effort to clarify the expectations of stakeholders and to communicate with them throughout the process. Our framework provides a structured approach that can be adopted by other researchers in the field, facilitating robust and comparable studies across different contexts. Constantly managing the possible challenges will lead to better success in longitudinal field trials and developing future technology-based solutions.