Digital Assistive Technologies (digital AT) show great potential to enhance workplace inclusion for people with disabilities (PwD) by reducing employment barriers, increasing autonomy, and improving task performance. However, their adoption in real-world workplaces remains limited. Consequently, more feasibility studies are needed to support broader integration and identify key factors for successful implementation across industries, considering employee and employer needs. This paper presents preliminary findings from a feasibility study conducted in the second phase of a two-phase field study investigating the implementation of digital AT in different industry sectors. Results highlight that successful deployment requires thoroughly assessing workplace-specific infrastructure, employer expectations, and usability factors. The study provides insights into essential conditions for digital AT adoption and offers a methodological framework for future large-scale research. By identifying key implementation requirements and usability characteristics, this research contributes to closing knowledge gaps and advancing the integration of digital AT in inclusive labor markets.