Injection drug use is especially risky for new injectors. To understand the social and environmental contexts in which risks occur, we interviewed individuals who had initiated injection within the past 3 years (n = 146, 69.2% male) about the circumstances and rationales for their initial injection events. Respondents typically initiated injection due to tolerance (49.3%) and/or for experimentation (61.1%). Most (86.2%) did not possess the technical skills required to self-inject, and relied on the assistance of someone older (58.5%). While low levels of syringe sharing (5.8%) were reported, a majority of respondents (60.5%) engaged in at least one type of behavioral risk. Female injectors were more likely than male injectors to rely on another individual (95.5 vs. 82.2%), often a sex partner (40.5 vs. 7.2%), for assistance. The diversity seen in early injection practices highlights the need for tailored prevention messages to reach this population prior to the onset of injection risk.