In June 2021, in the midst of the Palestinian Unity Intifada, Twitter users took to the platform to imagine a desired future in which Israel’s apartheid occupation and barriers fragmenting Palestinian communities no longer existed. The hashtag they used, #Tweet_Like_It’s_Free (#غرد_كانها_حرة), became an instant trend. In this article, the author examines a dataset of 600 of these tweets from June 2021 in order to explore the role of imagination in undoing fragmentation, emphasizing connection to the land, and disrupting a seemingly impenetrable status quo. The article argues that, despite limits to the use of digital media in the context of Israel’s settler-colonial occupation, playfulness and experimentation on social media are necessary political practices. Imaginative tweets do more than paint a picture; they narrate people’s right to movement and to hope, and reinforce their connection to the land and to each other across geographically fragmented communities in historic Palestine and the diaspora.