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The purpose of this study was to examine gendered perspectives on the digital divide, motivations for engaging in information technology (IT) education, and expectations regarding IT workforce participation in Kenya. Researchers interviewed 32 women and 31 men matriculating in an undergraduate IT-focused program at a Kenyan university. Interviewees reported that IT careers demand technical expertise, and a strong educational background in technology and business. However, their ability to meet these demands was hindered by significant national challenges such as restrictive IT policies, inadequate access to technology and educational resources, and a limited number of local firms that demonstrate the ability to manage advanced technology and IT workers. Women were particularly concerned about gender discrimination in the workplace. These findings imply that IT education and workforce entry require a complex mix of digital technologies, organizational capacity building, gender equity, and IT policy remedies.