The Arab League (LAS)-European Union (EU)'s relationship is trapped in a cycle of engagement followed by distrust and failure, due to regional dynamics and a lack of resolve. Although the potential for a broad-based partnership exists, the EU's inability to act at pivotal moments, including the pressing situation in Gaza, continues to hinder meaningful collaboration between the two organisations. The LAS-EU partnership, reinforced by shared concerns over regional crises, has been further tested by the deepening Israel-Palestine conflict, emphasising the need for a united front on humanitarian issues and peace processes. The history of their interactions shows a pattern of initial progress followed by periods of stagnation in the face of crises, signalling a need for resilient diplomatic strategies that can break this cycle and foster more consistent collaboration. Previous focus on security threats that are of particular concern to the EU indicates the latter's dominant role in setting the agenda. This dominance reflects underlying issues in the LAS-EU relationship, such as unbalanced power dynamics, partnerships based more on convenience than trust, and mutual misunderstandings. Given the current critical political conditions in the region, particularly the intensifying conflict between Israel and Palestine and the indescribable humanitarian crisis in Gaza, it is crucial for both the EU and LAS to rethink their approach to collaboration. The partnership is currently fragile, threatened by potential regression or even animosity due to mistrust and misunderstanding