Before you start
How to use this checklist
Print it, or open it on a second monitor, and tick each item as you complete it. The eight stages run in the order a real migration follows. If you are already mid-flight, jump to the stage that matches where you are. Nothing here is theoretical; every checkpoint maps to a decision or a failure mode seen on actual SharePoint 2016 cutovers.
| Item | What it means |
|---|---|
| July 14, 2026 | SharePoint 2016 reaches end of support. The same day, InfoPath reaches end of life. |
| May 18, 2026 | InfoPath form publishing is blocked. No more form changes can be pushed after this date. |
| 5,000 items | The SharePoint Online list view threshold. Bigger lists need indexed views or restructuring. |
| 100,000 items | Above this, migration tools cannot set unique permissions. Plan to split the list or library. |
| 400 characters | Maximum file path length the migration API accepts. Longer paths are rejected outright. |
| ~250 GB / day | Realistic throughput per migration agent for document-heavy content. Use it to size the timeline. |
The eight stages
- 1Discovery and inventory6 checkpoints
- 2Identity and permissions7 checkpoints
- 3Customizations and solutions5 checkpoints
- 4Workflows and forms5 checkpoints
- 5Third-party integrations4 checkpoints
- 6Data classification, compliance, retention5 checkpoints
- 7Migration and cutover6 checkpoints
- 8Post-migration validation and decommission6 checkpoints
Stage one
Discovery and inventory
6 checkpoints
- Inventory every site collection: URL, owner, storage size, item count (Get-SPSite + Export-Csv, or the SPMT scan).
- Flag every list or library over 5,000 items. These hit the SharePoint Online view limit and need indexed views or restructuring.
- Flag lists or libraries over 100,000 items. Migration tools cannot set unique permissions above this, so plan to split them.
- Surface stale sites with no edits in 12+ months. Decide archive or migrate before you move anything.
- Document every non-default content type and managed metadata term set.
- Estimate total size and timeline: plan by content type, document-heavy content typically moves near 250 GB/day per migration agent.
Stage two
Identity and permissions
7 checkpoints
- Confirm Microsoft Entra ID sync is healthy and complete.
- Map every on-prem security group used in SharePoint to its Microsoft 365 destination group.
- Find every site with broken permission inheritance. Record the owner and the reason.
- Remove orphaned permissions tied to disabled or deleted accounts.
- Audit external sharing: who has access, and is it still needed?
- Redesign permissions to match how access should work. Do not copy the old model unchanged.
- Set the tenant default sharing level before users arrive (anyone / org / specific people).
Stage three
Customizations and solutions
5 checkpoints
- List every deployed solution package (.wsp) and its scope.
- Treat farm solutions as a rebuild-or-retire decision. They have no equivalent in SharePoint Online.
- Identify code-based sandboxed solutions. Their code no longer runs in SharePoint Online.
- Decide per customization: rebuild with the SharePoint Framework (SPFx), replace with a built-in feature, or retire.
- Catalogue custom master pages, page layouts, and CSS. Most do not carry over to modern pages.
Stage four
Workflows and forms
5 checkpoints
- Inventory every SharePoint 2010 and 2013 workflow. Both engines are already retired in SharePoint Online and will not run there.
- Rebuild any workflow still needed in Power Automate; retire the rest.
- Inventory every InfoPath form. InfoPath retires July 14, 2026, and form publishing is blocked after May 18, 2026.
- Rebuild needed forms in Power Apps or Microsoft Forms. There is no automatic conversion.
- Run rebuilt flows and forms in parallel with the originals before cutover to confirm they match.
Stage five
Third-party integrations
4 checkpoints
- List every integration touching SharePoint (Nintex, K2, custom apps, line-of-business systems).
- Confirm each vendor supports SharePoint Online, or has a documented migration path.
- Update API endpoints, app registrations, and secrets for the new tenant.
- Re-test every integration end to end during the pilot wave.
Stage six
Data classification, compliance, retention
5 checkpoints
- Identify sites holding personal, financial, or otherwise regulated content.
- Recreate on-prem DLP rules as Microsoft Purview DLP policies. There is no automatic translation.
- Recreate on-prem retention and records policies as Purview retention labels and policies.
- Apply Microsoft Purview sensitivity labels to your highest-risk sites before migration.
- Document any legal holds or in-flight eDiscovery so they survive the move.
Stage seven
Migration and cutover
6 checkpoints
- Run a pilot wave first: one or two representative sites, fully validated before you scale up.
- Resolve checked-out files with no checked-in version. Migration tools skip them.
- Confirm version-history settings: decide how many versions to carry, and verify they arrive.
- Fix file paths over 400 characters and files over 250 GB. Both are rejected by the migration API.
- Freeze the source as read-only at cutover so no content changes mid-migration.
- Schedule large transfers for evenings and weekends, when throttling is lighter.
Stage eight
Post-migration validation and decommission
6 checkpoints
- Confirm every migrated site is searchable. Allow up to 24 hours for the index to catch up.
- Spot-check permissions on a 10% sample of migrated sites.
- Confirm sharing, retention, and DLP policies behave as expected.
- Walk a sample of users through the new sites and gather issues early.
- Keep the old farm read-only until validation is signed off. Then verify redirects and decommission.
- Confirm cyber-insurance and audit posture once the unsupported farm is retired.
If you get stuck
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This checklist is the planning half of the job. If the inventory turns up more than you want to take on solo (farm solutions to rebuild, InfoPath forms with no owner, permissions nobody can explain), that is the part TenantCraft does for a living. A discovery call is free, 25 minutes, and ends with a written scope, not a sales pitch.
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Checklist last reviewed May 15, 2026. SharePoint 2016 reaches end of support on July 14, 2026. Every checkpoint above should be closed (or consciously deferred) before that date.