Telework presents two quite distinct faces: longer, more irregular work schedules; yet potentially a better reconciliation of work and family life, provided it is promoted. Yet the outcomes are clearly ambivalent. Teleworking in itself is no guarantee of co-responsibility or the transformation of gender roles. There is a risk that it is perceived as the most ‘appropriate’ working arrangement for women, in a way that perpetuates gender roles and, even, widens the labour gap. To address this danger, socio-economic and cultural alliances, policies and regulations must all row in the same direction and take steps to eliminate patriarchal structures and systemic discrimination This contribution emphasizes that telework is not gender-neutral because it brings paid work into the domestic sphere, a traditionally feminine domain where productive and reproductive spaces overlap. The chapter analyses the impact that labour legislation and business practices have on women, and explores issues to which teleworking gives rise in relation to working time and work–life balance. Additionally, and with the focus more firmly on business practices, the work addresses the opportunities afforded by telework as a working-time arrangement.