Buying guide
· 8 min read· Updated 2026-05-04Upgrade to Windows Server 2025
Supported in-place upgrade paths to Windows Server 2025, the version-skip rules, downtime expectations and rollback options.
- Windows Server
- Upgrade
- IT
Supported upgrade matrix
| From | To 2025 | Notes |
|---|---|---|
| Server 2016 Standard/Datacenter | Two-step | Upgrade to 2019 or 2022 first |
| Server 2019 Standard | Direct | Same edition |
| Server 2019 Datacenter | Direct | Same edition |
| Server 2022 Standard | Direct | Same edition |
| Server 2022 Datacenter | Direct | Same edition |
| Server 2025 Eval | Direct | Run slmgr /ipk to swap key |
Pre-flight checklist
- · Full backup (system state + data). Test the restore on a separate machine.
- · Document IP, hostname, joined domain, roles installed.
- · Run setup.exe /scanonly to detect blockers — 3rd-party drivers, EOL antivirus.
- · For DCs: run adprep /forestprep and adprep /domainprep from the 2025 media on a 2019/2022 DC first.
- · Disable third-party antivirus during the upgrade.
Running the upgrade
Mount the 2025 ISO
Mount the ISO or attach the install media. Don't extract to a network share — local files only.
Launch setup.exe as admin
Choose 'Upgrade: Install Microsoft Server Operating System and keep files, settings, and applications'.
Pick the matching edition
Standard upgrades to Standard, Datacenter to Datacenter. Edition mismatch will fail.
Expect 60–90 minutes downtime
Multiple reboots. The 'Working on updates' phase is normal — do not interrupt.
Post-upgrade
Re-run Windows Update, verify roles, validate AD replication (repadmin /replsum) on DCs.
Rollback options
Windows.old retains the previous install for 10 days — you can roll back from Settings → Recovery → Go back to the previous version. After 10 days the rollback files are deleted and recovery requires bare-metal restore from your backup.
Frequently asked questions
- Can I move from Server Core to Desktop Experience during upgrade?
- No. The installation type (Core vs Desktop) cannot change during an in-place upgrade. Plan a clean install for that.
Recommended licenses
Windows Server 2022 Standard
Perpetual · 16-core · 2 VMs
16-core base Standard edition with up to 2 OSEs / Hyper-V containers.
Windows Server 2022 Datacenter
Perpetual · 16-core · Unlimited VMs
Unlimited virtualization for highly virtualized datacenter environments.
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