From legacy architecture to Cloudflare One

Cloudflare and CDW present a phased, risk-aware methodology for migrating large organizations from legacy VPN infrastructure to a SASE/Zero Trust architecture. The approach avoids 'big bang' cutovers by tiering applications by complexity (modern SaaS to legacy enterprise apps), using Cloudflare Access and Cloudflare Tunnel to 'wrap' legacy apps with MFA and SSO without rewriting code, and running a dual-client coexistence period for safe rollback. Key steps include auditing identity providers, mapping backend dependencies, separating strategy and implementation teams, and scaling in three phases. The methodology is positioned as treating migration as an application modernization project rather than a simple connectivity swap.