The years 1997–2020 were defined by intensive but ultimately failed peace negotiations under the auspices of the trilateral OSCE Minsk Group co-chairs (Russia, France, U.S.). They presented six major proposals, including the “Package” deals (1997), “Step-by-Step” approaches (1997), and the “Common State” concept (1998), which were all rejected by one or both sides, or undermined by domestic political turmoil, such as the 1998 resignation of Armenian President Ter-Petrossian. High-level bilateral negotiations between Presidents Kocharyan and Aliyev in 1999–2001 explored the Azerbaijani proposal of territorial swap (Nagorno-Karabakh for the Meghri corridor to Nakhichevan) as a starting point, then pivoting to a right of passage for Azerbaijan via Armenian territory, but stalled, notably after the 1999 Armenian parliament assassinations and Azerbaijan’s subsequent rejection at the Key West summit in 2001. The subsequent Prague Process led to the Basic/Madrid Principles (2006-2007), proposing a phased settlement: Armenian withdrawal from surrounding regions, an interim self-governance status for Nagorno-Karabakh, and a future plebiscite on final status. Despite endorsement by international leaders, Azerbaijan’s intransigence, fueled by rising oil revenues and military buildup, blocked the final agreement at the 2011 Kazan Summit. This diplomatic failure and increased Armenian provocative rhetoric and poor military preparation led to the decisive 2020 44-Day War, ultimately ending with a Russian-brokered ceasefire and a shift in regional power dynamics.