Windows Server Lifecycle Checklist

Use this checklist alongside your Server 2019 (and Server 2016) migration planning. Work through each section before committing to any upgrade or migration approach.

Inventory

• □ All Windows Server systems identified and listed
• □ Physical servers and virtual machines distinguished
• □ Each server's operating system version and build recorded
• □ Each server's primary role documented (AD, file, print, Hyper-V, RDS, SQL, application…)
• □ All applications installed on each server documented
• □ All users and systems that depend on each server identified

Lifecycle dates

• □ Microsoft Extended Support end date recorded for each OS version
• □ Application vendor support dates recorded for each installed application
• □ SQL Server lifecycle checked separately where SQL is present
• □ Hardware purchase date, warranty status and firmware currency checked
• □ Hardware compatibility with Server 2025 confirmed where applicable

Hardware assessment

• □ Purchase date and warranty period confirmed
• □ Firmware and BIOS currency checked against vendor releases
• □ RAID controller and disk health reviewed
• □ SSD wear levels checked where applicable
• □ Memory event log reviewed for errors
• □ Power supply and UPS battery condition reviewed
• □ Vendor hardware support availability confirmed
• □ TPM version and Server 2025 hardware requirements checked

Application compatibility

• □ Each application vendor contacted and asked about target OS support
• □ Windows Server 2025 compatibility confirmed or documented as pending
• □ Windows Server 2022 compatibility confirmed as fallback where needed
• □ SQL Server version and compatibility level reviewed
• □ Backup agent compatibility with target OS confirmed
• □ Endpoint protection compatibility confirmed
• □ Monitoring agent compatibility confirmed
• □ Print software and drivers reviewed

Security

• □ Current Windows security patches installed
• □ Application patches applied (SQL, backup agents, management tools)
• □ Endpoint protection in place and current
• □ External access reviewed (VPN, RDP, published services)
• □ Administrator and service account access reviewed
• □ Known vulnerability findings reviewed and remediated
• □ SMBv1 disabled
• □ RDP NLA configured

Backup and recovery

• □ Full backup confirmed successful
• □ System state backup confirmed where appropriate
• □ Application-aware backup confirmed for SQL and Exchange where present
• □ Database backups confirmed
• □ Offsite or immutable copy confirmed
• □ Recovery credentials and encryption keys documented
• □ Restore tested successfully to a non-production environment
• □ Recovery procedure documented

Target platform decision

• □ In-place upgrade to Server 2025 considered
• □ Migration to new server or virtual machine considered
• □ Cloud or SaaS replacement considered
• □ Workload retirement considered
• □ Target platform selected and documented
• □ Application vendor compatibility on target platform confirmed

Project planning

• □ Budget agreed
• □ Downtime windows agreed with the business
• □ Test plan written
• □ Rollback plan written
• □ Target completion date set
• □ Project owner identified

Retirement

• □ Data migrated and verified on new platform
• □ All services confirmed working on new platform
• □ Backups retained for appropriate period
• □ Old server removed from Active Directory and DNS
• □ Monitoring and backup agents removed from old server
• □ Licences reviewed
• □ Hardware securely disposed of or decommissioned appropriately