This study examined perceived needs, well-being, work/nonwork conflict and demands, and coping mechanisms among government and private schoolteachers in India while working from home during the COVID-19 pandemic. We employed a mixed method design, collecting 161 quantitative responses using questionnaires and 121 qualitative responses using open-ended questions. These were analyzed using inferential statistics and thematic analysis, respectively. Results highlight the negative impact of work/nonwork conflict on well-being. The missing work-home boundaries resulted in extended work hours, unorganized routines, and simultaneous work/nonwork demands. We describe the multifaceted nature of operational, pedagogical, and technological challenges faced by schoolteachers. We suggest psychological and operational resources and support mechanisms that can be developed at the family, school administration, and policy levels. Further, customized bundles of solutions are needed to address the variability in the challenges faced.