Remote work, propelled by digital tools and changing employee expectations, has reshaped team dynamics. Yet project leaders still lack evidence-based guidance on which teams struggle, when, and why. We analyze the first cross-regional dataset linking project-level outcomes to individual well-being: reports from 79 project managers. The design is convergent mixed-methods. A two-level logistic regression explained 42% of the variance in deadline slippage and revealed a three-way interaction that raised the odds of remote-work failure by 3.7 (p < .01). Quantitative predictors included technical disruptions, time-zone coordination issues, communication barriers, work-life balance conflicts, home-office distractions, limited resource access, and cybersecurity threats. Qualitative evidence described adaptive practices and mitigation tactics. Organizations invested in digital infrastructure, adopted unified communications tools, used AI-assisted scheduling platforms, and provided continuous training. The study offers practical guidance to strengthen resilience, productivity, and sustainability in remote project teams while clarifying organizational implications of digital transformation.