If you’re seeing any of these during planning, pay attention.

Discovery is still expanding two weeks before cutover. New dependencies surfacing that late aren’t a scope problem — they’re an assessment problem. If the environment wasn’t mapped thoroughly at the start, the plan isn’t ready for the window.

The rollback strategy is a sentence, not a procedure. “We’ll restore from backups if needed” isn’t a rollback plan. If there’s no timeline, no tested procedure, and no named decision-maker for when to pull the trigger, nobody has thought through what rollback looks like at 2am under pressure.

Stakeholder communication only runs one direction. IT sends updates. Business units receive them. If there’s no meaningful input coming back before cutover, that gap shows up during it.

None of these guarantee failure. All of them need to be closed before the cutover window opens.

When did a migration you were part of first show you something was wrong?

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