In the age of remarkable technological innovations such as AI, quantum computing, IoT, and blockchain, one could argue that the world is becoming an increasingly connected, advanced, enlightened, and peaceful place. Nevertheless, paradoxically, conflicts and wars are still born deeply rooted in complex strategic, historical, and economic dynamics, and continue to arise finding a direct representation in both physical and digital battlefields through powerful and dynamic environments like social media. This environment enabled unprecedented connectivity and ideas, thoughts, ideologies, and experiences exchange shaping the narrative, amplifying ideas, feelings, and experiences while directly addressing the underlying causes, dynamics, and implications of conflicts and war through a multifaceted and multi-nuanced approach. The outbreak and ongoing war in Ukraine took the international community off guard representing a significant turning point in the contemporary era that received immediately intensive global attention, united global humanitarian, and strategic efforts to support and help the ones in need, and reflected its geopolitical and economic global complexities, dynamics, and implications. At the same time, a high degree of disinformation and misinformation exists surrounding different aspects about this war e.g., actions taken, and impact produced on civilians, which contributes to creating an altered perspective of reality. While different conventional media and social media outlets together with research, governmental, and practitioner efforts revealed and reflected on the nature, major incidents, and their known impact on civilians and civilian objects as well as military personnel and military objects, yet limited attention and a lower voice is given through dedicated studies to thoughts and emotions of Ukrainian users in unconventional social media platforms like Telegram. This represents the knowledge gap tackled in this research by building a set of Machine Learning-based solutions for analysing the discourses and sentiments of Ukrainian users using the Design Science Research methodology in a Data Science research approach. From this analysis, reflection is provided to important days and incidents experienced by Ukrainian population since February 2022 in the first year of war.