Act 1 · Wake-up call

Acme has 14 months to leave Oracle.

A four-hour outage on Monday. The fourth in 18 months. Oracle support expires in 14 months — and the GSI says it'll take five years to migrate. The board wants an answer in nine days.

Gmail · Inbox6 days ago
From: Priya N., CEO
To: Miguel R., VP Engineering
Cc: Dana L., CFO · Sam K., GC
We can’t kick this down the road again.

Miguel,

Yesterday’s outage cost us $1.2M in missed orders and four customer escalations. That’s the fourth Sev-1 on OrdersService in 18 months. Same root cause every time — a 20-year-old WebSphere monolith on Oracle 12c that no one on the team has touched in years.

We’ve been deferring this migration for two budget cycles. Now the deadline is on top of us: Oracle Database EE goes out of support Dec 31, 2027. After that, no patches, no security fixes — anything left on Oracle becomes an open audit finding.

The GSI’s answer is $14M and five years. That finishes after Oracle support ends — meaning we’d also owe Oracle ~$8M for a 3-year Sustaining Support extension just to keep the lights on while the GSI catches up. Dana won’t sign that.

I need a real plan by the Dec 15 board meeting. Not a deck — a plan that finishes before Dec 31, 2027.

— Priya

Incident · INC-2026-1013SEV-1
OrdersService — thread-pool exhaustion at peak load
Mon, Apr 19 · resolved after 4h 12m · 1,400+ orders rejected
Missed revenue
$1.2M
Time to resolve
4h 12m
Customers paged
4 escalations
Service maintainer
None since 2019
Recurrence — same root cause, 4th time in 18 months
  • INC-2024-0418Apr 20242h 51m$0.6M
  • INC-2025-0214Feb 20253h 18m$0.9M
  • INC-2025-1107Nov 20255h 02m$1.1M
  • 18-mo total$3.8M lost
FINAL
signature due Dec 15
Statement of Work · Hyperscale GSI
$14M
fixed bid
5-year program 40 consultants· 38 services · 4 waves
Timeline vs. Oracle deadline
Today
Oracle EoL
GSI finish
First cutover · Month 14Portfolio finish · May 2030Oracle EoL · Dec 31, 202730 months past the deadline
Hidden cost: ~$8M Oracle Sustaining Support for the 3-year bridge while the GSI catches up.Real all-in: ~$22M · 14 months, 03 days until Oracle EoL.
The three options on the tableSame destination · same Oracle deadline
Option A
Extend Oracle support
All-in cost
≈ $8M
Timeline
3-yr Sustaining Support
Nothing migrated
  • Buys time, doesn’t solve the problem
  • Audit-finding risk grows every quarter
  • Defers — doesn’t kill — the $14M GSI bill
Option B
Sign the GSI quote
All-in cost
$14M + $8M
quote + Oracle bridge
Timeline
60 months
Done May 2030 · 30 mo late
  • First cutover lands Month 14 — already too late
  • Still owes Oracle for the 3-yr support gap
  • 40 consultants spun up, then spun down
Option CRecommended
Cursor Cloud Agents on AWS
The only option that finishes before Oracle EoL.
All-in cost
≈ $1.4M
agent compute + AWS
Timeline
22 days, first cutover
Whole portfolio by Feb 2028
  • 10 months ahead of the Oracle deadline
  • Senior reviewers still sign every gate
  • Same 4-person team — no new headcount, no SOW

Watch the same team use Cursor to ship a real production cutover in 22 days, not 14 months.