This talk explores how, within the context of a nationalist and settler-colonial project, gender roles can be both reinforced and, at times, transgressed and even deconstructed. It specifically focuses on the religious-Zionist settlers in the West Bank who live in isolated hilltop communities. Over the past two decades, the illegal outposts (ma’achazim halo choki’im) have become the primary tool by which religious-Zionist settlers appropriate land in the West Bank against Palestinian resistance. These outposts are typically small-scale rustic communities constructed on hilltops, deep inside West Bank territory. Almost all of them are relatively isolated and can be reached only by driving on a rugged gravel road. Based on almost two years of anthropological fieldwork during which I lived in one of these outposts in the Judean Desert, in this talk I focus on how many settlers are driven to “ascend” to the hilltop outposts in search of cultivating particular and surprising gender roles. In essence, we will see how for the young settler couples, the hilltops of the outposts serve as spaces where they can become what they imagine as proper “men” and “women” (raising children together in a tight-knit isolated frontier-style manner as each partner adheres to traditional gender roles), while for others it is the opposite: for them, the outposts is where this small-house-on-the-prairie fantasy can be transgressed (as they break from traditional gender roles, and partake in rather radical experiments in terms of gender performance and sexuality). I will show how among a specific segment of outpost society, most settlers, as they mature, shift from the first model to the second. Ultimately, by focusing on the outpost people, my aim is to illuminate the relationship between nationalism, religion, settler-colonialism, and gender.