The practice of concurrent sexual partnerships (CP) is posited to be a contributor to the elevated risk of HIV transmission among youth in Malawi. The lens through which Malawian youth conceptualize the practices of CP and condom use has yet to be fully explored. The current study--a secondary data analysis of semi-structured in-depth interviews (n = 19) with Malawian youth aged 18 to 22 years--addresses this gap. Participants were interviewed about their sexual relationships and behavior, as well as their perceptions and knowledge regarding condom use and CP. In order to ensure that youth engaged in CP were oversampled, the recruitment process asked potential respondents to self-identify whether they currently participated in CP. Of the total sample (n = 19), 13 self-identified as currently engaging in CP. Data were analyzed using a grounded theory approach. This qualitative study highlights a disconnect between the high level of knowledge youth exhibit about HIV prevention methods and their actual reported condom use and CP behaviors. While some youth claimed to use condoms, their discourse demonstrated fluidity in that use changed over time, or interest in changing behavior was expressed, or was inconsistent between partnerships. The disconnect between knowledge of the consequences of risky sexual behavior and actual behavior was most evident among inconsistent condom users engaged in CP. This finding indicates knowledge alone has a limited role in the adoption of lower risk behaviors such as condom use and reduction of CP among youth. Moreover, findings from this study can inform HIV prevention programs operating in Malawi and the sub-Saharan Africa region by enabling them to provide tailored, more persuasive health promotion and prevention messaging.