For decades, enterprises have relied on SQL Server for critical applications, but face challenges with downtime, costs, and modernization. Migrating SQL Server to Azure SQL is a common strategy to leverage AI and cloud-native trends. Successful migrations hinge on early answers to three key questions: acceptable downtime, post-migration costs, and the right target platform. Data administrators and architects must consider technical aspects before, during, and after modernization to avoid long-term issues.Several business triggers necessitate SQL modernization, including end-of-support timelines for older SQL Server versions, cybersecurity concerns, and the need to reinvest IT budgets. Capacity constraints due to business growth also drive data modernization to scalable platforms like Azure SQL. The three major blockers to SQL modernization are downtime risk, cost uncertainty, and compatibility with different Azure SQL offerings. Offline migration paths that cause significant downtime are often a concern, though zero-downtime options exist.Cost uncertainties arise from improper evaluation of infrastructure sizing, licensing, and disaster recovery. Choosing the right target platform is crucial, as a simple lift-and-shift to Azure VMs may forgo the benefits of PaaS services like Azure SQL Managed Instance. Azure SQL Managed Instance is presented as a solution that addresses all three migration blockers by offering near-full SQL Server compatibility with PaaS benefits. It provides robust resiliency through local redundancy, zone redundancy across availability zones, and cross-region disaster recovery with failover groups.Cost governance for enterprise buyers is facilitated by Azure SQL MI's flexible pricing, including right-sizing and serverless options. Azure SQL DB Hyperscale offers bundled services and independent compute/storage scaling, ideal for variable workloads. Azure Hybrid Benefit allows customers to leverage existing SQL Server investments for cost savings. Free tiers for Azure SQL DB and Azure SQL MI enable cost-effective proof-of-concepts and evaluations.For scenarios where data migration is restricted, Azure Arc's Pay-As-You-Go licensing provides cloud-style SQL licensing for any environment. Reserved instances offer further discounts for committed usage. Azure SQL supports diverse cloud cost models, empowering decision-makers to select the optimal solution for their workloads.