Cimpress, the global mass customization company behind Vistaprint, returned to profitability in fiscal 2026 with revenue climbing 10% to $3.74 billion — a signal that its deliberate shift toward higher-value customers is taking hold. Yet the market received the news with quiet skepticism, as the deeper question is not whether the company can earn, but whether it can convert those earnings into the cash needed to sustain a balance sheet still carrying nearly three times its EBITDA in debt. Recovery and risk are traveling together here, and the distance between them is measured in cash flow.