Although working from home and various other forms of flexible work are often presented as measures to strengthen work–life balance, research depicts a less optimistic picture. Previous research has shown that the impact of telework on work–home conflict is controversial, depending on various factors that are also frequently gender-specific. In this study, the authors evaluate and compare the effects of external expectations (i.e., an organizational overwork climate) and internal expectations (i.e., high personal standards) on changes in work–home conflict between working men and women during the COVID-19 pandemic in Lithuania. Both types of expectations were associated with difficulties reconciling work and private life. Due to their interactions with stereotypical gender roles, organizational expectations encouraging overtime work had a more pronounced effect on male employees. Results suggest that an overwork climate within organizations is a problem not only for employees’ well-being but also poses a risk to gender equality in work and private life.