Multicultural issues have become central to the current global discourse following massive migration waves and the rise of identity politics, informing major trends in multicultural education, including in the arts. In 2011, the learner community at Hamidrasha—the Faculty of Arts at Beit Berl College in Israel—became multicultural with the opening of the preparatory school for art for Palestinian-Arab students. Using the visual auto-ethnography approach, this article reviews the process and change I have undergone, as a Jewish participant observer and lecturer, as part of the broader diversification of Hamidrasha. It focuses on my encounter with the image narratives of the Palestinian-Arab students and their encounters with their Jewish peers, and my process from cultural to multicultural compotence. I will discuss the dilemmas and challenges raised by these narratives with emphasis on the ability of art education to highlight cultural gaps as well as offer paths to reconciliation.