Overview
This guide outlines a pragmatic, low-risk approach to move workloads from VMware vSphere/ESXi to Microsoft Hyper-V while keeping downtime to an absolute minimum. It combines pre-seeding data, repeatable validation, and a short, scripted cutover window.
1) Prerequisites & Planning
- Inventory: list VMs, OS versions, CPU/RAM, disks, NICs, VLANs/portgroups, IPs, dependencies, backup/DR status.
 - Target design: choose Hyper-V host versions, cluster or standalone, storage (CSV/S2D/SAN), and vSwitch layout.
 - Maintenance window: pick a cutover slot; define acceptable downtime (e.g., <5–15 minutes per VM).
 - Backups & rollback: verified backup or snapshot on VMware, plus a tested revert plan.
 - Tools ready: disk conversion utility (e.g., StarWind V2V or qemu-img), file replication (Robocopy/Rsync), and scripts.
 
2) Prepare Hyper-V & Convert Disks
- Create matching virtual switches and VLAN tagging on Hyper-V.
 - For each VM, convert VMDK → VHDX (fixed or dynamic). Prefer Generation 2 VMs for UEFI-capable OS; use Generation 1 for legacy BIOS OS.
 - Attach converted VHDX files to a placeholder VM on Hyper-V (do not boot yet).
 - Pre-create VM settings (CPU/Memory, checkpoints disabled for cutover, static MAC if needed).
 
3) Pre-Seed Data to Minimize Downtime
- Windows guests: Use 
Robocopywith multi-threading to pre-copy application/data volumes to attached VHDX (e.g., from a helper or via SMB). Example:robocopy D:\\Data \\HyperVHost\\Share\\VM\\Data /MIR /Z /R:1 /W:1 /MT:32 /XD Temp - Linux guests: Use 
rsyncfor initial sync to the VHDX mount, preserving ownership and ACLs. Example:rsync -aHAX --numeric-ids --info=progress2 /data/ /mnt/hv/data/ - Repeat the sync (incremental) right before cutover to reduce delta size.
 
4) Prepare OS for Hyper-V
- Uninstall VMware Tools on the source VM (or plan to remove on first boot). Hyper-V uses its own integration services (in-box for modern Windows; Linux uses LIS/virtio equivalents).
 - Change NIC type expectations: vmxnet3 → Hyper-V synthetic adapter. Note current IP settings for re-apply.
 - Ensure bootloader compatibility (UEFI/BIOS). For Gen2, confirm GPT/UEFI support; otherwise use Gen1.
 
5) Isolated Test Boot
- Boot the converted VM on Hyper-V in an isolated network (no production connectivity).
 - Verify: OS boots, disks & partitions correct, services start, app logs clean, time sync, RDP/SSH works.
 - Install/verify Hyper-V integration services as applicable; remove residual vSphere agents.
 - Shut down the test VM after validation; keep it ready for final delta sync.
 
6) Cutover Runbook (Per VM)
- Announce maintenance start; freeze changes at application layer (stop app services or set read-only).
 - Take a final VMware snapshot or backup (rollback point).
 - Power off the VMware VM.
 - Run a final incremental Robocopy/Rsync to sync the last delta to the VHDX on Hyper-V.
 - On Hyper-V, attach the up-to-date VHDX and configure NICs (VLAN, static MAC if needed). Apply the original IP/DNS.
 - Boot the VM on Hyper-V. Validate quickly: ping, RDP/SSH, app health checks, logs.
 - DNS, load balancer, and firewall updates (if IP or network changed). Flush ARP caches if necessary.
 - Hand back to users; monitor closely for the first 30–60 minutes.
 
7) Option: Use System Center VMM (Enterprise)
- SCVMM can orchestrate VMware discovery and conversion to Hyper-V at scale.
 - Still plan a controlled cutover: pre-checks, window, rollback, and scripted validation.
 
8) Post-Migration Hardening
- Re-enable backups on Hyper-V targets; run and verify restore tests.
 - Enable monitoring/alerts; update CMDB and diagrams.
 - Remove VMware snapshots and decommission old VMs only after a defined observation period.
 
Rollback Plan (If Needed)
- Power off Hyper-V VM; revert DNS/LB/firewall to VMware endpoints.
 - Revert VMware snapshot; start services; announce service restoration.
 - Investigate issue offline; repeat conversion after fix.
 
Common Pitfalls & Tips
- UEFI/BIOS mismatch (Gen2 vs Gen1) → choose correct VM generation.
 - Missing drivers after conversion → ensure integration services and storage/network drivers are present.
 - Time skew after cutover → verify NTP/Hyper-V time sync settings.
 - MAC/IP changes breaking licensing → preserve MAC or re-activate licenses as required.
 
Example Timeline (Per VM)
- T-7 to T-2 days: initial conversion + test boot (isolated), fix issues.
 - T-1 hour: announce window, stop non-essential jobs, incremental sync.
 - T-0: power off VMware, final delta sync (1–5 min typical), boot on Hyper-V, quick checks (2–10 min).
 - T+30 min: user validation, monitoring, close change.