Job Title: Systems Administrator – Windows Server MigrationLocation: Toronto, ON (4x onsite a week)Employment Type: ContractPay Rate: CAD$45 - $50/HR INCInterview Type: Face 2 Face (Onsite Interview Only)Job DescriptionWe are seeking two experienced Systems Administrators to join our IT development team for a critical Windows Server migration project.You will be responsible for programmatically migrating legacy systems from Windows Server 2019 to Windows Server 2022, ensuring minimal downtime and maintaining system integrity.This is a hands-on technical role requiring solid scripting automation skills and experience with enterprise migration projects.Key ResponsibilitiesDevelop automated scripts and procedures for migrating Windows Server 2019 environments to Windows Server 2022Migrate and configure legacy VB components, ASP applications, and .NET web servicesRegister all required certificatesTransition Windows services, scheduled tasks, and batch jobs to the new environmentCreate comprehensive migration documentation and rollback proceduresCollaborate with development teams to troubleshoot application compatibility issuesImplement monitoring and validation processes to ensure successful migrationMaintain system security and compliance standards throughout the migration processProvide post-migration support and optimizationTechnical RequirementsEssential Skills5+ years experience in Windows Server administration (2016/2019/2022)Expert-level scripting abilities with PowerShell for automation and migration tasksProficiency with additional scripting languages (Bash, Python,



or similar)Hands-on experience with IIS configuration and migration (IIS 10 to IIS 11)Proven experience migrating legacy applications including:VB6 components and ASP classic applications.NET Framework web applications and web servicesWindows services and scheduled tasksStrong knowledge of batch job migration and task scheduler managementExperience with server imaging, cloning, and configuration managementUnderstanding of Active Directory, DNS, DHCP, and other core Windows servicesDesirable SkillsKnowledge of containerization (Docker) for legacy application isolationFamiliarity with CI/CD pipelines for deployment automationExperience with monitoring tools (Dynatrace, Zabbix, or similar)Understanding of networking concepts and firewall configurationPrevious experience with data center migrations or cloud migrationsProfessional RequirementsBachelor's degree in Computer Science, Information Technology, or equivalent experienceProven track record of successful enterprise-scale migration projectsAbility to create detailed technical documentation and proceduresStrong problem-solving skills and ability to troubleshoot complex system issuesExcellent communication skills for collaborating with technical and non-technical stakeholdersRelevant Microsoft certifications (MCSE, MCSA) preferred but not requiredExperience working in Agile/Scrum project environmentsProject-Specific RequirementsExperience with phased migration approaches and cutover planningKnowledge of dependency mapping for interconnected systemsAbility to work with legacy systems while planning modernization pathwaysExperience with testing methodologies for migration validationUnderstanding of business continuity planning during migration activitiesDisclaimer: AI tools may assist in the recruitment process; however, all hiring decisions are made by the recruitment team based on a comprehensive evaluation of candidates.

📌 Systems Administrator - C$45 - C$50 An Hour (Toronto)
🏢 Aarorn Technologies
📍 Toronto