In a recent webinar titled “From Oracle to CockroachDB: Lessons from Real Migrations,” experts Rohan Joshi and Alistair Parry explored how organizations successfully transitioned critical workloads from Oracle to CockroachDB, addressing challenges such as schema conversion and PL/SQL refactoring. The session highlighted how CockroachDB's MOLT (Migrate Off Legacy Technology) toolkit streamlines the migration process by providing a structured approach from planning to validation, ensuring transparency and control. The discussion underscored the importance of resilience over speed, with CockroachDB offering enhanced uptime compared to Oracle, as demonstrated in benchmark tests. Additionally, the webinar emphasized the significance of automation in database modernization, with Cockroach Labs developing AI tools to ease migration complexities, and advised starting with SQL-compliant and OLTP-focused workloads. Ultimately, the migration to CockroachDB is presented as a means to relieve engineering teams from maintenance burdens, enabling them to concentrate on innovation and organizational goals.