aws-samples / aws-samples/technical-notes-for-microsoft-workloads-on-aws
Add a new section for Windows Server 2016 to 2022 in-place upgrade, mirroring the existing 2016→2019 guide structure.
- Dominant language
- PowerShell
- Stars
- 2
- Forks
- 8
- Avg merge
- 2h 42m
- Merged PRs (30d)
- 6
Description
## Motivation
- Windows Server 2016 reaches end of support in January 2027
- Customers may want to skip 2019 and go directly to 2022 (Microsoft supports this two-version jump via installation media)
- Windows Server 2022 offers longer support runway (mainstream support through October 2026, extended through October 2031)
- The existing 2016→2019 SSM automation can be adapted with minimal changes for a 2022 target
## What's Included
- **SSM Automation Documents:**
- `Windows-2016-to-2022-Upgrade.json` (65 steps, adapted from 2016→2019)
- `windows-2016-to-2022-precheck.json` (11 steps)
- **Documentation:**
- Upgrade Guide (with both AWS CLI and PowerShell commands)
- IAM Roles Setup
- Automation Flowchart
- **Key differences from 2016→2019:**
- Targets `Windows 2022 {lang} Installation Media` snapshots
- Verifies OS build 20348.x (Server 2022)
- .NET 4.8 in-box (vs 4.7.2 on 2019)
- Pinned CUs target Server 2022
## Testing
- Tested successfully on t3.large (us-east-1)
- Source: Windows Server 2016 Base AMI (license-included)
- Result: Windows Server 2022 Datacenter, build 20348
- All 65 automation steps passed
- Total upgrade time: ~37 minutes
## Microsoft Reference
[Plan your Windows Server upgrade](https://learn.microsoft.com/en-us/windows-server/get-started/install-upgrade-migrate?tabs=media) confirms 2016→2022 is a supported in-place upgrade path via installation media.
## TODO before merge
- [ ] Replace placeholder CU URLs with real Server 2022 June 2026 cumulative update URLs
- [ ] Verify 2022 installation media snapshots exist in all target regions
- [ ] Add IAM Roles Setup page (adapt from 2019 version)
- [ ] Add Automation Flowchart (adapt from 2019 version)
Contributor guide
Research direction
Start by comparing Windows-2016-to-2022-Upgrade.json and windows-2016-to-2022-precheck.json with the existing 2016→2019 automation, then review the Upgrade Guide and related 2019 IAM Roles Setup and Automation Flowchart materials. Verify the Server 2022 CU URLs and installation-media snapshots across target regions. Done means the documents, guide, IAM page, and flowchart are complete and the 65-step automation succeeds on the stated test setup.
Written by the indexing model from the issue text.
Assessment
- Tech stack
- aws, powershell
- Domain
- cloud, devops, documentation
- Issue type
- Feature
- Difficulty
- 4/5
- Estimated time
- 3-5 days
- Activity status
- Quiet
- Clarity
- Mostly clear
- Newbie friendliness
- 56/100