Have you noticed that the migrations that look simpler on the surface are often the ones that produce the worst cutover surprises?

My M365 migration work started in 2019; Exchange mailboxes to M365 via BitTitan MigrationWiz, SharePoint migration via ShareGate. From there: Azure and Entra ID work, then in 2025 and 2026 running full tenant-to-tenant acquisition migrations covering M365, Teams, OneDrive, SharePoint, and SSO.

What gets harder with experience isn’t the technical execution. It’s setting accurate expectations. A migration that looks like a straightforward 300 plus mailbox move to a stakeholder is often sitting on top of an undocumented shared mailbox structure, 12 distribution lists with stale membership, and a source tenant where nobody knows who the global admin is anymore.

The AZ-305, AZ-104, MCSE: Productivity, and BitTitan dual certifications give me the architecture and tooling foundation. The years of production migrations is what tells me which questions to ask before we start.

I write about these patterns at CloudMigrationMindset.com if you want to dig further.

What’s the most unexpected migration discovery you’ve had to work around?

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