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Migrating from old to new core platforms remains one of the genuinely difficult problems in insurance technology. First-time core modernization projects routinely surprise their leaders. Core insurance systems encode decades of business logic, https://relais-intl.com/digital-transformation-trends-in-the-insurance-industry/, relais-intl.com, regulatory accommodation, and operational reality. They contain hundreds of edge cases nobody remembers building in. Product variations launched and never quite retired all live in the existing platforms. Modernization initiatives meet this reality piece by piece throughout their lifecycles. What initially appears to be a defined scope grow as analysis exposes more edge cases. Initial dates almost always slip. This pattern is reliable enough that it deserves planning for, not lamenting. Better-performing initiatives build realistic schedules around what consistently happens. They favour incremental transitions over big-bang replacements. Lower-complexity policies transition before higher-complexity ones. Phased migration limits the impact of unexpected problems. It also takes longer in nominal terms. The longer schedule prevents larger problems. Change management requires resources comparable to technical implementation. Underwriters, claims handlers, and customer service teams using the new system require investment in their adoption. The insurers achieving meaningful core modernization exhibit these consistent patterns.