HubMub
-
Aarorn Technologies Inc

Systems Administrator (Windows Server Migration)

Aarorn Technologies Inc
Canada · Contract · Mid-Senior
Job Title: Systems Administrator – Windows Server Migration

Location: Toronto, ON (4x onsite a week)

Employment Type: Contract

Pay Rate: CAD$45 - $50/HR INC

Interview Type: Face 2 Face (Onsite Interview Only)

Job Description

We 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 strong scripting automation skills and experience with enterprise migration projects.

Key Responsibilities

  • Develop automated scripts and procedures for migrating Windows Server 2019 environments to Windows Server 2022
  • Migrate and configure legacy VB components, ASP applications, and .NET web services
  • Register all required certificates
  • Transition Windows services, scheduled tasks, and batch jobs to the new environment
  • Create comprehensive migration documentation and rollback procedures
  • Collaborate with development teams to troubleshoot application compatibility issues
  • Implement monitoring and validation processes to ensure successful migration
  • Maintain system security and compliance standards throughout the migration process
  • Provide post-migration support and optimization

Technical Requirements

Essential Skills

  • 5+ years experience in Windows Server administration (2016/2019/2022)
  • Expert-level scripting abilities with PowerShell for automation and migration tasks
  • Proficiency 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 services
  • Windows services and scheduled tasks
  • Strong knowledge of batch job migration and task scheduler management
  • Experience with server imaging, cloning, and configuration management
  • Understanding of Active Directory, DNS, DHCP, and other core Windows services

Desirable Skills

  • Knowledge of containerization (Docker) for legacy application isolation
  • Familiarity with CI/CD pipelines for deployment automation
  • Experience with monitoring tools (Dynatrace, Zabbix, or similar)
  • Understanding of networking concepts and firewall configuration
  • Previous experience with data center migrations or cloud migrations

Professional Requirements

  • Bachelor’s degree in Computer Science, Information Technology, or equivalent experience
  • Proven track record of successful enterprise-scale migration projects
  • Ability to create detailed technical documentation and procedures
  • Strong problem-solving skills and ability to troubleshoot complex system issues
  • Excellent communication skills for collaborating with technical and non-technical stakeholders
  • Relevant Microsoft certifications (MCSE, MCSA) preferred but not required
  • Experience working in Agile/Scrum project environments

Project-Specific Requirements

  • Experience with phased migration approaches and cutover planning
  • Knowledge of dependency mapping for interconnected systems
  • Ability to work with legacy systems while planning modernization pathways
  • Experience with testing methodologies for migration validation
  • Understanding of business continuity planning during migration activities

Disclaimer: 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.

Key Skills

Ranked by relevance

server windows server active directory containerization powershell firewall ai tools python docker cloud bash dhcp cicd mcsa dns ai
Login to Apply
🇨🇦

Country Guide

Canada

Express Entry & tech-friendly immigration

Posted
Feb 12, 2026
Type
Contract
Level
Mid-Senior
Location
Toronto
Company
Aarorn Technologies Inc

Industries

IT Services IT Consulting

Categories

Information Technology

Related Jobs

3 roles aligned with this opportunity

View all jobs
View Job Details
Resource Corner
Related

DevOps Engineer

2026-05-27

Contract
Entry
Australia
IT Services
Engineering
View Job Details
Optimyze Consulting
Related

Network Administrator (All Genders)

2026-05-28

Full-time
Mid-Senior
Germany
Telecommunications
Information Technology
View Job Details
Groupe SII
Related

Software Developer C# / .NET (m/w/x)

2026-05-21

Full-time
Not Applicable
Germany
IT Services
Engineering