You’re two weeks into your migration project, and you can already see that the cutover will be more difficult than what was promised in the kickoff presentation?

I can usually tell within the first two week after multiple migration programs have been completed and more than 1,000 mailboxes have been migrated if a project is on track for a smooth cutover, or if it’s heading toward a prolonged post-migration incident. The signals are consistent.

The first sign is a runbook which is only a list of tasks. A task list explains to the team what they should do when things go according to plan. A runbook will tell them what to do if it doesn’t. If rollback procedures and failure threshold triggers are not documented prior to the first batch run, these decisions will be made under pressure at the cutover.

The second sign is an unassessed environment. If an engineer reads the item-level errors reports, they will find orphaned accounts, objects with mail enabled but no mailbox, and authentication policies that are in conflict with the tenant configuration at the destination during MigrationWiz trials migrations. If no one ran the migration trial or reviewed the output, these problems will be waiting for cutover.

The third signal is coexistence which has not been planned. During the transition period, users on both sides of tenant-to-tenant migrations are collaborating. If no one has defined the mail routes between them during the transition period, how calendar sharing works, or how Teams interoperability functions, these gaps will become urgent problems after the cutover.

The fourth signal is that identity should be treated as a prerequisite rather than a separate workstream. Entra ID synchronization sequence, domain rehoming sequence, hybrid identity configuration, and timing of Entra ID must be validated prior to mailbox migration, not as a pre-task completed the week before cutover.

The fifth sign is a lack of a Hyper Care Support plan. A migration without a defined support structure after cutover means that the migration engineer becomes part of the support team. A 5-person team that managed 500+ clients in multiple post-migration stages worked because the structure was designed prior to cutover and not assembled by whoever was available after.

The sixth sign is that PowerShell is not being used pro-actively. Bulk operations to validate and verify pre-migration and post-migration are done one record at a a time through admin portals. This is a scaling issue that compounds after and during cutover.

The seventh sign is the lack of stakeholder communications. Users who don’t know what is changing and when, or who to contact if something doesn’t work, generate a high volume of help desk traffic, which turns manageable issues into long incidents.

These signals are all fixable. The more you wait to see these signals, the more expensive it becomes.

Which of these signals are you currently experiencing on your project?

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