Azure migration is where $5 million budgets meet reality and discover they needed $8 million plus another year. Microsoft's migration tooling assumes simple scenarios: Windows Server 2016+ with default configurations and public endpoints. Enterprise migrations involve Windows Server 2008 R2 that can't be upgraded, applications with undocumented dependencies, and security requirements that prohibit internet connectivity. Azure Migrate generates beautiful assessment reports while completely missing the integration complexity that kills migration projects.
Successful migration requires answering 55 questions about each application before touching Azure Migrate. Who owns this application? What databases does it connect to? Which file shares does it access? What SSL certificates will expire during migration? How do users authenticate? Real migration projects fail on these integration details, not Azure technical complexity. You need discovery tools that reveal actual dependencies, not just OS inventory. You need assessment frameworks that evaluate business continuity risk, not just Azure compatibility. And you need executives who understand that migration takes 18-24 months, not the 6 months promised in the business case.
