Tier 2 IT Support Engineer - Hybrid

Adastra; Chicago (IL); Hybrid; USD 65,000 - 85,000; Full time

Job summary

Adastra in Chicago is seeking an IT Help Desk Analyst to provide advanced technical support across end-user systems and core infrastructure, including servers, virtualization, networking, and databases. This role acts as an escalation point for Level I support and helps maintain system stability, performance, and security.

You will troubleshoot complex desktop, server, and network issues, support Windows/Mac, Active Directory, VMware/Hyper-V/Azure, DNS/DHCP, and ensure proper documentation and

Qualifications

• 3–5+ years of IT support experience in a Help Desk/Desktop/Infrastructure role.
• Strong troubleshooting skills across servers, networking, and end-user systems.
• Hands-on experience with Windows Server (2016/2019/2022), AD/GP, and virtualization (VMware/Hyper‑V/Azure).
• Solid networking fundamentals (DNS, DHCP, TCP/IP, VPN).
• Experience with ticketing systems such as ServiceNow or Jira.

Responsibilities

• Act as Tier 2 escalation point for complex desktop, application, and system issues.
• Maintain and troubleshoot Windows Server environments, patching, performance, and uptime.
• Administer and support virtual environments (VMware, Hyper-V, or Azure VMs).
• Troubleshoot LAN/WAN, VPN, and connectivity issues; support switches, firewalls, and wireless infra.
• Provide basic database administration support (SQL Server or similar) and enforce security policies.

Skills

Windows Server

Active Directory

Virtualization

Networking basics

Help desk tools

Tools

ServiceNow

Jira

Job description

Adastra in Chicago is seeking an IT Help Desk Analyst to provide advanced technical support across end-user systems and core infrastructure, including servers, virtualization, networking, and databases. This role acts as an escalation point for Level I support and helps maintain system stability, performance, and security.

You will troubleshoot complex desktop, server, and network issues, support Windows/Mac, Active Directory, VMware/Hyper-V/Azure, DNS/DHCP, and ensure proper documentation and