Servers · Upgrade and migration

Windows Server end-of-support upgrades, planned and done

Servers running Windows Server versions that no longer get security updates are the easiest way for a business to fail a cyber-insurance questionnaire. IT Perfection plans the upgrade, builds the new server or virtual machine, moves the roles and data, and retires the old server cleanly.

Windows Server 2012 / 2016 / 2019Physical or virtualRoles and data migrated
Network engineer patching fiber and cabling in a server rack
1 · ReviewWe review hosts, storage, patch levels and recovery options on your servers.

When to call us

When the upgrade is due

  • A server runs Windows Server 2012 R2, 2016 or 2019 and support has ended or ends soon
  • Your cyber-insurance or compliance questionnaire asks about unsupported operating systems
  • The server hardware is also out of warranty
  • Applications on the server still work but the vendor only supports newer Windows versions
  • You want to move the workload to Hyper-V, VMware or Azure at the same time
  • Nobody is sure what the server does any more

What you get

What the upgrade includes

Every role, share, application and dependency on the old server is listed before anything is moved.

Inventory and plan

Roles, shares, applications, services and who depends on them, with a written plan and written quote.

New server or VM

Current Windows Server built on new hardware, Hyper-V, VMware or an Azure virtual machine.

Server hardware installation

Active Directory

Domain controllers upgraded in the right order, FSMO roles and DNS moved.

Domain controller upgrade

Files and applications

File shares, permissions, print queues and line-of-business applications moved and tested.

Backup and cut-over

Full backup before cut-over, change made at an agreed time, rollback ready.

Backup and disaster recovery

Retirement

Old server removed from the domain and from monitoring, documentation updated.

How the work runs

How the upgrade runs

  1. Review

    Inventory of the old server and a written plan.

  2. Build

    New server or VM installed and patched.

  3. Move

    Roles, data and applications migrated.

  4. Test

    Users and applications checked before the old server goes.

  5. Retire

    Old server decommissioned and documented.

Every engagement starts with a written scope and a clear quote, so you know the expected cost before work starts. How pricing works

Technology and guides

Technology involved

Windows Server 2022 and 2025Hyper-VVMwareAzure virtual machinesActive DirectoryDFS and file servicesVeeam and Windows Server Backup

Free guides from our IT library on this topic:

Ali Hassani, CISSP and Certified CISO, IT Perfection

Who does the work

Ali Hassani, CISO

IT Perfection is led by Ali Hassani, who has 25+ years of experience in IT operations, Microsoft infrastructure, networking and cybersecurity. Design, implementation and troubleshooting work is planned and reviewed by Ali personally.

ISC2 CISSP certification badgeEC-Council Certified CISO badgeCisco CCNP Routing and Switching badgeMicrosoft Certified Solutions Expert Server Infrastructure badgeMicrosoft Certified Systems Engineer badgeMicrosoft Certified Systems Administrator badgeCisco CCNA Cybersecurity badgeMicrosoft Certified IT Professional badge

Need an independent security audit, compliance readiness or vCISO support instead? IT Perfection handles design, implementation and day-to-day IT; OC Security Audit is the related cybersecurity brand for audits, compliance readiness and vCISO work.

Related services

Often needed together

Server migration

View service

VMware and Hyper-V virtualization

View service

Azure migration

View service

Questions

Windows Server upgrades: common questions

Can you upgrade the server in place?

Sometimes, but a fresh install on a new server or VM is usually safer. The plan says which is right for each server.

Will there be downtime?

Some, at cut-over. It is scheduled outside business hours and the old server stays available until the new one is proven.

Our application vendor says they support only an older Windows version. What then?

That is found during the inventory. Options are an application upgrade, a separate isolated server, or keeping the old server off the internet until the vendor catches up.

Can the new server be in Azure instead?

Yes. Many file and application servers move to an Azure virtual machine during the upgrade.

What does it cost?

It depends on the number of servers, roles and applications. The first 30-minute review is free, and you get a written quote.

Get off unsupported Windows Server before the next questionnaire asks.

Start with the free 30-minute review. No obligation, and you leave with a clear list of what is fine and what needs attention.

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