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TL;DR Collapsed a billing model from à-la-carte features to plans-only, in four safe phases. Unified authorization across web, API, and MCP so all three obey one permission layer. Fixed a legacy Oracle password-sync writing to the wrong column. Four repos moved today. Here's the thread that ties most of them together: one source of truth beats two. Billing: plans-only Spent most of the day migrating a SaaS off per-feature à-la-carte subscriptions and onto plans-only entitlements. The interesting part isn't the model — it's doing it without a billing outage: seed plans, switch reads to plans, backfill every org, then delete the old machinery. Expand/contract, four deployable phases. Full write-up in the focused post. One permission layer for three surfaces An ops tool exposed the same actions three ways — web UI, API, and an MCP server for agent access. The bug: each surface checked authorization slightly differently, so an MCP tool could allow something the web UI blocked. The fix was to make the MCP tools gate on the same permission layer as everything else, so: web ─┐ API ─┼─► one permission check ─► allow / deny MCP ─┘ TL;DR: web ≡ API ≡ MCP — three doors, one lock. Also added a dedicated support-engineer role scoped for debugging without handing over the keys to everything, plus identity/diagnostics/SLA read tools so an agent can answer "why didn't this notification send?" without shell access. Before After Each surface authorizes its own way Single permission check, shared MCP tool could out-permission the UI MCP bound to the same guard No debug-scoped role support_engineer role, read-only diagnostics Legacy Oracle password sync Smaller but sharp: a password reset was writing to the wrong Oracle column and also touching a date_modified field it had no business updating. Routed the student reset to the correct password column and dropped the stray write. Lesson with legacy schemas — the column that looks right and the column the app actually reads from are not a

TL;DR Moved a SaaS from à-la-carte feature subscriptions (pay per feature) to plans-only (pay for a tier, get its features). Did it in four phases so nothing broke mid-flight: seed plans → gate on plans → migrate orgs → delete the old machinery. Lesson: model migrations are safest as expand → migrate → contract , not a big-bang swap. The problem The old billing let an org subscribe to individual features à la carte. Flexible on paper, painful in practice: entitlement logic had two sources of truth (per-feature subscriptions and an implicit plan), and every gate had to check both. Time to collapse it into one model — you buy a plan , the plan carries the features. The trap with this kind of change is the temptation to rip out the old columns and ship. Do that and every in-flight subscription, every gate check, and every webhook that still speaks the old language breaks at once. The phased plan I ran it as four ordered migrations. Each phase is deployable on its own and leaves the app working. Phase What it does Why this order F1 Seed Plans into the prerequisite chain New model must exist before anything reads it F2 Gate features on the plan, not the feature-sub Reads switch over while writes still dual-run F3 Deploy op migrates existing orgs onto a plan Backfill — nobody left on the old model F4 Remove the à-la-carte machinery Contract — safe only after F3 This is the expand/contract pattern applied to a domain model, not just a schema. Expand (F1) adds the new thing alongside the old. Migrate (F2–F3) moves reads then data. Contract (F4) deletes the old thing once nothing points at it. F1 seed F2 gate on plan F3 backfill orgs F4 drop features ┌────────┐ ┌──────────────┐ ┌──────────────┐ ┌──────────────┐ │ plans │ --> │ reads: plan │ -> │ every org on │ -> │ delete a-la- │ │ exist │ │ writes: both │ │ a real plan │ │ carte code │ └────────┘ └──────────────┘ └──────────────┘ └──────────────┘ safe safe safe safe Gating on the plan The gate collapses to a single question