Abstarct: Objective: The main objective of this study is to identify and prioritize the dark sides and barriers of digital transformation in the future of work (emphasizing factors such as employee resistance, resource scarcity, and infrastructure weaknesses) to enhance organizational resilience and sustainability. Methodology: This research is applied in purpose and employs a mixed-methods (qualitative-quantitative) approach. Initially, 7 key barriers/dark aspects were screened and validated using the Fuzzy Delphi technique. Subsequently, the baxse Criterion Method (BCM) was utilized to weight these criteria with minimal inconsistency. Finally, the novel Opportunity Losses-baxsed Polar Coordinate Distance (OPLO-POCOD) technique was applied to prioritize the criteria and evaluate organizational performance baxsed on the Degree of Opportunity Loss (DOL). The case study was conducted on 9 organizations operating in Iraq. Findings: The BCM results indicated that "Employee resistance to changes" (0.3488), "Lack of financial resources and budget" (0.2325), and "Absence of supportive laws and regulations" (0.1163) hold the highest importance from the experts' perspective. Conversely, the OPLO-POCOD analysis revealed that the lowest Degree of Opportunity Loss (DOL) belongs to "Traditional organizational culture" (0.0356) and "Lack of financial resources" (0.0462), which can be improved through quick corrective actions. In contrast, the highest gaps (highest DOL) are related to "Employee resistance to changes" (0.4394) and "Lack of performance evaluation and monitoring systems" (0.2015), necessitating long-term strategic planning. Furthermore, performance evaluation showed that organizations 7, 6, and 8 demonstrated the best status in managing these barriers. Conclusion: The studied organizations require a systematic approach to overcome the dark sides of transformation and move towards sustainability. The primary focus should be on short-term, targeted investments in criteria with rapid improvement potential (such as resource optimization and regulatory adjustments). Meanwhile, fundamental issues like managing employee resistance and enhancing top management awareness necessitate long-term strategic planning, continuous training, and deep cultural shifts.