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Plan a Cloud Architecture Migration

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Your question is Plan a Cloud Architecture Migration. Take a moment with it on the right.

Talk me through your thinking if you like. When you're confident, submit your answer and I'll grade it like a real screen (7/10 or better passes).

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Scenario

You are the Engineering Manager for a healthcare operations platform that is moving a core service from a single-region setup to a cloud-based, multi-region architecture. The current system supports customer-facing workflows that cannot tolerate extended downtime, and the migration must preserve auditability and data integrity while improving reliability and deployment speed. Product wants the new architecture live before the next customer renewal cycle, Security wants stronger isolation and logging, and Support is already seeing incidents tied to the current infrastructure. The catch is that the team is small, the legacy service has undocumented dependencies, and one senior engineer who understands the current system is only available part-time.

Constraints

DetailValue
Team size6 engineers, 1 EM, 1 TPM
Migration scope3 services, 2 databases, 1 queueing layer
Availability target99.9% during migration window
Cutover window8 weeks
Compliance constraintsAudit logs retained for 7 years; PHI access must remain least-privilege
Rollback requirementFull rollback within 30 minutes

Question

How would you plan and execute this migration, including the trade-offs you would make, the risks you would watch most closely, and how you would keep stakeholders aligned if the plan changes?