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.



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 installationActive Directory
Domain controllers upgraded in the right order, FSMO roles and DNS moved.
Domain controller upgradeFiles 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 recoveryRetirement
Old server removed from the domain and from monitoring, documentation updated.
How the work runs
How the upgrade runs
Review
Inventory of the old server and a written plan.
Build
New server or VM installed and patched.
Move
Roles, data and applications migrated.
Test
Users and applications checked before the old server goes.
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
Free guides from our IT library on this topic:

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.








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 serviceVMware and Hyper-V virtualization
View serviceAzure migration
View serviceQuestions
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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