Cyprus, as one of the most geopolitically strategic regions in the Eastern Mediterranean, is a place where the complexities of a bi-communal structure are acutely experienced. The concept of a federal system—defined as a form of governance bringing together communities with different identities, cultures, or languages under a single political framework—has frequently been proposed as one of the most viable solutions for the unification of the island, aiming to ensure equal political rights and address security concerns for both communities. This study aims to describe and analyze, within an academic framework, the development and applicability of federal and alternative solution models to the Cyprus issue between 1990 and 2020. Conducted through a qualitative methodology, the research employs content analysis based on official documents, political discourse by leaders, and international reports. The findings reveal that while federalism has been supported for many years as a solution model, confidence in this approach declined significantly following the rejection of the Annan Plan in 2004 and the failure of the Crans-Montana negotiations in 2017. The study also evaluates the feasibility of non-federal alternatives from strategic, legal, and diplomatic perspectives. The period between 1990 and 2020 marks the closest historical phase to a comprehensive settlement. In recent years, Turkiye, as one of the guarantor states, has shifted away from the federal model and now advocates for a two-state political framework as a more realistic path to resolution. This study offers a source-based evaluation of the applicability of various proposed solutions.