Non-homeless youths outperform their homeless peers in school even if they live in extreme poverty. This disadvantage can have long-term consequences for engagement with and navigation of wider society. In this paper we examine how differences in achievement could be tackled outside of school through the re-envisioning of ecologies of digital education. Through interviews, design workshops, and a street visit with a total of 20 homeless young adults during a three-week engagement with a centre for people of low social stability in Bucharest, Romania, we examine the perceptions of education among street involved youth or adults. We identify the core values, aspirations, opportunities and barriers for education among these people, including survival, friendship, learning networks, and curiosity. These findings resulted in five implications for design: learning 'happens', learning 'works', designing for distanced learning, designing for the social politics of learning, and designing artefacts of everyday learning. These show the importance and necessity of educational reform in the field of HCI.