This article explores border crossing and the Palestinian city as a literary metropolis—two major themes in the works of emerging Palestinian novelists in Israel. It looks at the “re-Palestinization” of urban space by writers who belong to a post-Oslo generation of Palestinian intellectuals that left villages and small towns in Israel to go and study, work, and live in the city. What distinguishes the literature of this generation is its negotiation of border crossing in a fragmented geography and its engagement with the city as a space of paradoxical encounter between a national imaginary and a settler-colonial reality. Based on a critical reading of their works, the article argues that Adania Shibli and Ibtisam Azem challenge colonial border discourse, exposing the ongoing Zionist erasure of the Palestinian city and creating a new topography for Palestinian literature. The article also traces the role of these writers in the “twinning” of Haifa and Ramallah starting in the late 1990s, and it examines how this literary and cultural “sisterhood” informs spatial resistance.