The convergence of employment tax systems and cybersecurity vulnerabilities poses significant challenges during the annual tax season, when digital transactions and sensitive data exchanges reach their peak. This paper examines the growing threats of cyberattacks targeting employment tax processes, with a focus on phishing schemes, ransomware, identity theft, and payroll data breaches. As governments and organisations increasingly adopt e-filing and cloud-based payroll systems, cybercriminals exploit weak authentication protocols and human error to gain unauthorised access to taxpayer information. The study explores how the complexity of employment tax compliance amplifies risk exposure, particularly in small and medium-sized enterprises with limited cybersecurity infrastructure. Using recent data and case studies, the research highlights how fraudulent tax filings and employer impersonation have become prevalent attack vectors. Moreover, it evaluates the role of artificial intelligence and machine learning in detecting anomalies within digital tax filings and enhancing preventive controls. The findings underscore the need for a multi-layered security strategy, combining employee awareness, regulatory compliance, and advanced encryption, to mitigate cyber threats during tax season. The paper concludes by emphasising the importance of continuous monitoring, cross-sector collaboration, and integrating cybersecurity frameworks into tax administration systems to ensure data integrity, taxpayer confidence, and a sustainable digital transformation.