A broad scan of negative feedback from multiple online platforms shows that despite its position as one of the world’s largest technology companies, Microsoft continues to face persistent dissatisfaction and backlash on several fronts; most prominently, customer service and support failures top the list, with many users reporting extremely long wait times, unhelpful automated systems, difficulty reaching human agents, unresolved support tickets, and widespread frustration with account access and recovery processes. Linked closely to this is widespread software quality and user experience criticism, especially around Windows 11 and integrated AI features such as Copilot and Recall, where many users feel forced updates and intrusive integrations have introduced bugs, confusing interfaces, and a loss of control rather than enhancing productivity, eroding confidence that Microsoft is prioritizing stability and reliability. Another major theme is pricing, subscription models, and perceived value, with long-standing customers highlighting the shift away from perpetual licenses toward subscription services that they feel lock them into recurring fees without commensurate improvements, coupled with complaints about lost data and account issues that compound the feeling of poor return on investment. Additionally, discussions in employee forums reflect internal culture stresses and concerns about layoffs, work-life balance, and management practices that have left some former and current staff critical of leadership transparency and organisational stability. To address these core issues, Microsoft could significantly strengthen its support infrastructure by ensuring accessible human assistance alongside automated tools, prioritise rigorous testing and clearer communication around major software changes, re-evaluate its pricing and subscription strategies with greater flexibility and transparency for long-term users, and enhance internal management practices and communication to support employee morale and clarity around strategic shifts – steps that together could improve trust and user satisfaction in both consumers and its workforce.