This article compares the considerations, expectations, and realizations of Hong Kongers migrating to Taiwan and Australia. Based on interviews with 22 Hong Konger migrants, we identified some key drivers for Hong Kongers who moved to Taiwan or Australia. The findings add insights into the spatial–temporal nexus of migration and extend the static push–pull model by including migrants’ changing perceptions about the sociopolitical conditions of different destinations. In addition to offering a more nuanced understanding of migrants’ perceptions of and adaptations to the sociopolitical environment of the host society, we highlight that, after moving to Taiwan or Australia, Hong Kong migrants experience a gap between what they imagined at the time of migrating and the reality (political, social, and/or cultural). The imagination of the sociopolitical community in the destination countries before they leave and the gap between pre- and post-migration experiences constitute the “unsettling” characteristic of the recent Hong Kong exodus after 2019.