Welfare technology (WT) use is increasingly advocated to facilitate aging in place. However, it remains unclear how older adults and homecare staff perceive these digital technologies in practice. This qualitative study investigated the ways in which current WT either facilitated or fell short in supporting older adults in their daily lives and homecare staff at work. Four key themes were developed using thematic analysis: 1) Successes and challenges with ease of use (i.e., how simple it is to interact with the WT); 2) Successes and challenges with usefulness (i.e., how effective the WT is in achieving its intended purpose); 3) Challenges with appearance, sounds and physical location; and 4) Challenges with technical maintenance and vulnerabilities. Findings revealed paradoxes in both older adult and homecare staff user perceptions. For instance, some successes with WT's usefulness were highlighted, like GPS safety alarms in supporting older adult independence. However, challenges in usefulness were also exposed, like staff hiding "overused" safety alarms. Except for the medication robot, none of the WT devices clearly alleviated anticipated homecare staff shortages. WT perceived as auditorily or visually inadequate, that required more effort than users could comfortably manage, or that organizations could seamlessly integrate, were generally regarded as challenging. To overcome such challenges, greater involvement from older adults and homecare staff in the design and implementation of WT within homecare contexts is necessary. Refined criteria for prescribing WT to individuals, particularly regarding cognitive status, are additionally recommended by the researchers.