In the complex manufacturing landscape, machine failures and unplanned stoppages frequently lead to production delays, energy wastage, and diminished product quality. Maintenance costs can represent a high portion of total production expenses, making efficient equipment maintenance crucial for operational success. The integration of cyber-manufacturing—marked by smart machines, the Internet of Things (IoT), and cloud computing—poses new challenges, as evidenced by a significant uptick in cyber-attacks. This study develops models to evaluate the financial implications and benefits of cybersecurity within maintenance outsourcing agreements. It proposes strategies for aligning the interests of manufacturers, who are vulnerable to cyber threats, with contractors accounting for potential cyber-attack costs. The findings offer actionable insights for optimizing profitability under the dual threats of mechanical failures and cyber-attacks, providing comprehensive strategies for managing maintenance and cybersecurity investments. This research is vital for manufacturers seeking to safeguard their operations and maximize profits amidst increasing cyber threats.