In a world where digital technology is omnipresent, North Korea stands as an outlier, with most citizens uninformed about its existence. This study explores the experiences of North Korean defectors as they transition to a highly digitally connected society—South Korea. Through 21 semi-structured interviews, we initially investigate the critical needs and challenges they encounter during their transitions. Then, we examine the role of digital technology as they adapt to the highly connected digital environment of South Korea. Our findings highlight that social media serves as a double-edged sword, providing the freedom to construct a desired identity while accentuating the gap between their real and ideal selves. This empirical research offers insights into how an underrepresented population navigates the digital landscape during life transitions, shedding light on the drawbacks and ways to better address their needs.