Large-scale software systems frequently experience architectural degradation, which poses significant challenges to maintainability, scalability, and system effectiveness. To systematically uncover and analyze these architectural issues, we conducted an empirical study involving senior architects and developers from three major organizations. Our methodology began with an exploratory focus group where participants collaboratively identified and documented architectural challenges and pain points. Initial categorization yielded four challenge areas. These empirically identified challenges were then mapped to existing peer-reviewed literature to contextualize them within the broader field. We validated our findings through structured focus group sessions involving additional senior practitioners, ensuring robust and comprehensive perspectives. Our results highlight specific areas where architectural degradation impacts software development practices and system quality, and underline the complexity of addressing these issues at scale. This paper presents detailed insights from our empirical approach, along with implications for researchers and practitioners aiming to create awareness about architectural degradation in large-scale software systems.