The Ultimate MSP Checklist for Customer Data Migration to Microsoft 365

Helping MSPs Navigate Seamless, Secure, and Scalable Cloud Migrations

Microsoft 365 has emerged as the preferred productivity suite for companies of all sizes in today's cloud-first world. It's no surprise that many businesses are switching from legacy systems to Microsoft 365 because of its enterprise-grade security and smooth collaboration features. Although the destination is appealing, there may be obstacles along the way, particularly in the case of data migration.

As an MSP, you are aware of the stakes. Your clients rely on you to transfer their important data without any delays, interruptions, or data loss. Even the most seasoned teams may overlook a detail that could affect the success of the migration because there are so many moving components.

Why MSPs Need a Bulletproof Migration Checklist

Data migrations are more than just a technical undertaking for Managed Service Providers (MSPs). Long-term client relationships are shaped by these strategic initiatives. MSPs are under pressure to complete migrations flawlessly, with the least amount of disruption and the highest level of security, as more businesses switch to Microsoft 365 to embrace cloud productivity and collaboration.

Let's face it, though: every migration has a unique set of complications, whether they are related to coexisting systems, legacy infrastructure, data sprawl, or permissions issues. For this reason, a well-defined, repeatable checklist is not only useful, but necessary.

In this article, we’ll walk you through the MSP migration checklist that ensures smooth transitions to Microsoft 365, powered by Cloudiway’s secure, scalable, and SaaS-based migration platform.

These best practices are applicable whether you're migrating from Google Workspace, Box, legacy Exchange, or SharePoint.

Pre-Migration Planning: Establishing the Foundation

1. Define Project Scope & Stakeholders

• List all of the destination Microsoft 365 tenants and source platforms (such as G Suite, Box, and Exchange).
• Clearly define the migration's objectives and key performance indicators (KPIs), such as complete permissions preservation and zero downtime.
• Engage all stakeholders: IT leads, department heads, compliance officers.

2. Evaluate the Source Environment

• Conduct a full audit: How many users, groups, mailboxes, and files are we migrating?
• Are there any legacy systems, PST files, or hidden archives to consider?
• Use Cloudiway’s discovery tools to generate pre-migration reports for content size, metadata, and potential blockers.

3. Validate Target Readiness

• Ensure Microsoft 365 licenses are provisioned.
• Confirm domain DNS is configured.
• Create destination mailboxes, OneDrive accounts, Teams, and SharePoint sites.

Cloudiway Tip: Use the Cloudiway Platform to simulate your migration and detect errors in advance with built-in test tools.

Migration Setup: Configuring the Tools

4. Create Connectors and Credentials

• Register source and destination connectors in the Cloudiway portal.
• Securely configure OAuth tokens or service accounts (e.g., for Google or Exchange).
• Grant necessary admin permissions—least privilege principle applies.

5. Build a Migration Matrix

• Map users, groups, aliases, and shared resources.
• Handle duplicate accounts or merged tenants.
• Use CSV import in Cloudiway for bulk mapping.

6. Configure Migration Options

• Select migration scope: mail, OneDrive, Google Shared Drives, SharePoint, Teams.
• Choose delta pass settings (for minimal downtime).
• Enable metadata, permissions, versioning, and timestamps if required.

Cloudiway Tip: Migrations are admin-driven and user-independent. No need for user intervention—perfect for enterprise-scale projects.

Execution: Running the Migration Like a Pro

7. Run Pilot Migrations

• Always test with a small group.
• Validate mailbox fidelity, folder structure, metadata, and file integrity.
• Review logs in the Cloudiway dashboard.

8. Monitor Live Migration Progress

• Track migration per user/resource.
• Watch for errors or throttling issues (Cloudiway auto-retries API calls!).
• Communicate progress with real-time status dashboards.

9. Perform Delta Passes

• After initial data sync, schedule delta passes to capture changes.
• This ensures zero data loss during final cutover.

Cloudiway Tip: For high-volume moves, use parallel connectors to scale migration throughput.

Post-Migration: Validation & Clean-Up

10. Perform Post-Migration Validation

• Validate migrated content for completeness.
• Ensure permissions and sharing links are intact.
• Test mail routing, OneDrive sync, Teams functionality, etc.

11. Redirect DNS or MX Records

• Final cutover should include mail routing updates.
• Decommission legacy mailboxes after verification.

12. Archive Reports & Compliance Logs

• Download audit reports from the Cloudiway platform.
• Store for compliance, client records, and billing validation.

Cloudiway Tip: Use the built-in logging and error reports to validate each migration batch and meet MSP compliance needs.

Bonus Tips for MSPs: How to Deliver Maximum Value

13. Plan for Coexistence (if needed)

• Hybrid or phased migrations may require calendar sharing or mail forwarding.
• Cloudiway supports calendar free/busy between tenants and platforms.

14. Offer Training and Support Post-Migration

• Help clients adapt to Microsoft 365 with quick-start guides or live Q&A.
• Ensure IT teams know how to use SharePoint, Teams, and Outlook effectively.

15. Upsell Value-Added Services

• Post-migration governance setup
• Ongoing M365 management and optimization
• Security audits and data lifecycle strategies

Why MSPs Choose Cloudiway

Cloudiway is purpose-built for MSPs managing migrations at scale. Our cloud-native platform offers:

• Multi-tenant dashboard to manage multiple customer projects
• No agent installation
• Delta passes and automatic retries for resilient transfers
• Secure, compliant architecture (ISO 27001 aligned)
• Support for mail, OneDrive, Teams, SharePoint, Google Drive, Box, etc.

Whether you're migrating one small business or an entire enterprise group, Cloudiway gives you the power, flexibility, and support you need.

Final Thoughts: Migration Success is in the Details

Your clients aren't satisfied with a simple lift-and-shift. They anticipate no disruption, security, and strategy. MSPs can confidently tackle any Microsoft 365 migration by using this checklist.

Additionally, when you work with Cloudiway as your technology partner, you do more than simply transfer data; you open the door to a more seamless, intelligent, and scalable future for your customers.

Want to try it yourself? Book a demo or start a free trial with Cloudiway today