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In-place upgrade directly from Windows 7 → Windows 11 is not supported, but organizations can perform a staged upgrade by first upgrading devices to Windows 10 and then performing a supported in-place upgrade to Windows 11. Devices that cannot meet Windows 11 hardware requirements will still require a clean OS install or replacement.
Perform the Microsoft 365 / cloud data migration first (mailboxes → Exchange Online, user files → OneDrive/SharePoint). This preserves user data and minimizes risk when devices are reimaged or replaced. Use Known Folder Move (OneDrive KFM) or USMT to preserve user files and settings. Use Intune + Windows Autopilot (or Autopilot for existing devices) to provision Windows 11 where possible — this replaces SCCM for new/provisioned devices and integrates smoothly with cloud identities.
Consider the following step migration plan
Discovery & Inventory
- Inventory hardware (CPU, RAM, disk, TPM, Secure Boot, firmware). Windows 11 minimums (TPM 2.0, UEFI/Secure Boot, 64-bit CPU, 4 GB RAM, 64 GB disk) are mandatory. Flag devices that cannot meet these requirements.
- Collect app inventory and compatibility data (line-of-business apps, drivers). Use vendor compatibility lists or test VMs.
Output: spreadsheet with PC model, TPM status, firmware type, disk space, apps, and whether it can run Windows 10 and/or Windows 11.
Decide: refresh vs staged upgrade
- For many Windows 7-era devices, retrofitting (TPM, UEFI, etc.) is impractical — plan to replace these.
- Devices that meet Windows 10 (but not Windows 11) requirements can be upgraded first to Windows 10 to extend their lifecycle while preparing users for the modern OS.
- Devices that meet Windows 11 requirements can follow a two-step path:
- Windows 7 → Windows 10 (in-place or reimage).
- Windows 10 → Windows 11 (supported in-place upgrade).
Microsoft only supports in-place upgrades from Windows 10 → Windows 11, so ensure intermediate upgrades reach Windows 10 21H2 or later before moving to Windows 11.
Identity + Microsoft 365 Pre-Migration
- Decide your identity model:
- Cloud-only (Azure AD) — users created in Entra ID; simplest if retiring on-prem AD.
- Hybrid (Azure AD Connect) — sync existing credentials; common during staged migrations.
- Migrate mailboxes to Exchange Online and files to OneDrive or SharePoint. Having these cloud services active before OS changes ensures that data and user identity remain intact throughout device transitions.
Protect user files: OneDrive KFM + backups
- Enable OneDrive Known Folder Move (redirect Desktop/Documents/Pictures) via policy or staged rollout to sync user files to the cloud.
- For settings not covered by OneDrive, use USMT (User State Migration Tool) or a third-party equivalent to capture and restore user state between OS upgrades.
Choose a provisioning approach
- New PCs: use Windows Autopilot + Intune to automatically enroll, apply policies, and deploy apps.
- Existing PCs:
- Stage 1 – Upgrade Windows 7 → Windows 10 (via ISO, MDT, Intune, or third-party deployment).
- Stage 2 – Upgrade Windows 10 → Windows 11 (supported in-place).
- Alternatively, use Autopilot for existing devices (import hardware hashes) or reimage using Intune/MDT when performing clean installs.
Preserve settings and applications
- User data and settings: restore using OneDrive KFM + USMT (registry/app settings).
- Run
ScanStateon old OS → store migration data →LoadStateafter upgrade or reimage.
- Run
- Applications:
- Reinstall or redeploy supported apps via Intune, company portal, or package manager.
- For legacy applications, test on Windows 10/11 first; if incompatible, use virtualization (Azure Virtual Desktop, App-V, MSIX) or third-party migration tools (Zinstall, Laplink PCMover).
Pilot
- Select small user groups (1–3 departments).
- Migrate mailboxes and enable OneDrive KFM.
- Capture user state (USMT) or verify OneDrive sync.
- For pilot devices:
- Test both upgrade paths (Win7→Win10→Win11) and fresh reimage scenarios.
- Enroll upgraded/reimaged devices in Intune/Autopilot.
- Validate restored profiles, apps, printers, and sign-in behavior (Azure AD join/hybrid join).
- Refine based on pilot feedback and adjust tooling/policies.
Rollout
- Expand gradually (10% → 30% → 100%) with support staff available.
- Maintain rollback options and verified backups.
- Communicate clearly what will change, what’s preserved, and expected downtime.
Post-migration fixes
- Re-evaluate Group Policies inherited from Windows Server 2008 R2; modernize them for Windows 10/11.
- Consider raising forest/domain functional levels when ready.
- Move toward modern identity and security (Conditional Access, MFA, Intune compliance, Defender for Endpoint).
Decommission and secure
- Securely wipe or retire Windows 7 machines.
- Remove legacy infrastructure once all devices are migrated.
- Ensure all new devices comply with Windows Update for Business policies managed via Intune.
Common challenges & compatibility issues
- Hardware limitations: many Win7-era PCs fail TPM 2.0 / UEFI requirements — replacement likely.
- Driver availability: older hardware may lack Win10/11 drivers — test early.
- Legacy LOB apps: may require compatibility shims, virtualization, or redevelopment.
- Profiles and personalization: without OneDrive KFM, use USMT or migration tools.
- Licensing: OEM Windows 7 licenses may not transfer; ensure compliance for Win10/11.
- Identity transition: Azure AD or hybrid join changes sign-in/SSO behavior — plan user training.
- No SCCM/WSUS: replace with Intune + Windows Update for Business for cloud-based management.
Native Microsoft tools
- Microsoft 365 (Exchange Online, OneDrive, SharePoint): cloud mail + file hosting.
- Azure AD / Azure AD Connect: identity and sync.
- Intune (MEM): policy management, app deployment, and Windows Update for Business.
- Windows Autopilot: zero-touch provisioning for new or existing devices.
- User State Migration Tool (USMT): capture and restore profiles and settings at scale.
- OneDrive Known Folder Move (KFM): sync critical user folders to the cloud.
Third-party tools
- Zinstall / Laplink PCMover: transfer programs, settings, and files from Windows 7 to Windows 10 or 11 when reinstallation is impractical.
- Application compatibility / virtualization tools: Microsoft App-V, MSIX, VMware ThinApp for legacy apps.
Example pilot checklist (per device/user)
- Verify hardware compatibility (Win10 and Win11) or flag for replacement.
- Backup data and validate.
- Enable OneDrive KFM (verify sync).
- Run USMT
ScanState(if needed). - Upgrade path test:
- Step 1: Windows 7 → Windows 10 (ISO/Intune/MDT).
- Step 2: Windows 10 → Windows 11 (in-place).
- Enroll device in Intune / Autopilot.
- Install apps via Intune and run
LoadState(USMT). - Validate access to mail, files, printers, and business apps.
- Gather feedback and refine process.
Quick risk mitigations & best practices
- Migrate user data to OneDrive before any upgrade.
- Use USMT for settings OneDrive does not capture.
- Pilot small and iterate before large-scale rollout.
- Keep a fallback device and document rollback procedures.
- Communicate early with users on backups and downtime.
- Document app install order and printer configurations.
Given your setup (Windows Server 2016 AD, domain/forest at 2008 R2, Windows 7 clients, no SCCM/WSUS):
- Assess hardware — categorize devices for replacement, Win10-only, or Win11-ready.
- Establish Microsoft 365 identity and data migration first (mail + OneDrive).
- Perform staged upgrade: Windows 7 → Windows 10 → Windows 11 for eligible devices.
- Adopt Intune + Autopilot for management and provisioning.
- Use OneDrive and USMT to preserve profiles and settings across each upgrade step.
More at https://learn.microsoft.com/en-us/answers/questions/673598/win-7-to-win-10-or-11, https://learn.microsoft.com/en-us/sharepoint/redirect-known-folders, https://learn.microsoft.com/en-us/autopilot/existing-devices, https://learn.microsoft.com/en-us/windows/whats-new/windows-11-requirements, https://learn.microsoft.com/en-us/windows/deployment/usmt/usmt-overview
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hth
Marcin
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