SharePoint to S3 Migration Checklist

TL;DR

Migrating a sprawling SharePoint environment to Amazon S3, is a high-stakes, multi-phase project where preparation is everything. AWS admins know the risks: overlooked dependencies, metadata loss, and user confusion can cripple business operations faster than any technical glitch. If you want a frictionless, resilient migration that delivers long-term value, you need more than the right tools. You need a plan rooted in AWS best practices and proven assessment methods. We share our checklist for SharePoint to S3 migration…

Why SharePoint to S3 Migration Is Complex

SharePoint’s power comes with complexity: years of nested sites, custom workflows, and undocumented integrations. Migrating from SharePoint to S3 means tackling metadata mapping, permissions rewiring, and unwinding legacy dependencies. Overestimating the ease or speed of this transition is a classic pitfall. A successful migration is grounded in technical discovery, executive buy-in, and crystal-clear impact analysis.

The Strategic Assessment Approach

The foundation of every successful migration is a structured pre-migration assessment framework tailored for the AWS cloud. Start with these four assessment pillars:

Discovery

Inventory and audit your entire SharePoint environment—every site, library, and content type.

Analysis

Map dependencies, estimate migration effort, and identify compliance and security gaps.

Planning

Develop an actionable, milestone-driven migration roadmap and communication plan.

Validation

Test tools and migration strategies on a subset of content. Identify and mitigate risks early.

Deliverables should include a content inventory with metadata, a dependency map, a user impact matrix, and a phased migration timeline.

Implementation Steps

1. Content Discovery and Inventory

Automate site-level inventory using PowerShell or third-party tools to capture file types, sizes, and usage. Analyze for duplicates, obsolete content, and records requiring custom retention in S3. Output: A comprehensive spreadsheet for planning and clean-up.

2. Dependency Mapping and Integration Analysis

Document all SharePoint automations, third-party add-ins, and links to M365 apps. Tag each dependency as critical or nonessential. Assess replacements: Workflows might map to Lambda; sharing to S3 bucket policies. Build a matrix capturing complexity ratings and recommended AWS services.

3. User Impact Analysis

Identify stakeholders and typical user journeys. Plan user training and phased rollouts. Map out where permissions, search, or workflows will change—then communicate, mitigate, and test.

4. Timeline and Resource Planning

Start with a pilot migration, then batch by department or sensitivity level. Define owner accountability, allocate time for surprises, and lock in test/validate cycles. Prioritize rollback procedures and post-migration optimization.

Best Practices & Tips

Pilot migration on noncritical content to test and refine methods.
Use automation for discovery, mapping, and validation.
Engage stakeholders from day one, maintaining clear, continuous communication.
Carefully document processes, decisions, and governance changes.
Come prepared for ongoing S3 management—your journey doesn’t end at “cutover.”