Move a Guidewire deployment to a new platform or release without breaking running policies and claims — on-prem→cloud cutover (config reconciliation, data migration, parallel-run validation), in-place version upgrade (e.g., 202403→202503) with deprecated-API regression coverage, rehearsal-driven cutover with rollback path mid-flight, and broker/claimant communication so users hit the right system at the right time.
SkillScore63Maintained
Automatic
◆DevOps & SRE packguidewiremigrationupgrade
Last verified 8/30/2026
What it changes
Passed 14 of 23 test cases with the skill, and 9 of 23 without it.
Without skill38%
With skill63%
Checks it passed that the model alone missed
Executes the Phase 1 abort runbook by re-enabling source writes.
Triggers an immediate Phase 1 abort when source database read lag exceeds 60 seconds.
Establishes Phase 5 plus 1 hour as the cutoff point after which forward fix becomes mandatory.
and 5 more in the full report
7 fixed8 passed either way8 still failing1 broke
Pass-rate lift
+25 pp
Tokens
+79%
Agent turns
0%
Response time
-18%
Model gemini-3.6-flashMeasured 8/30/2026v115 of 24 cases passed with skill · 23 comparable
Tokens, turns and time describe resource use, not a dollar price.
See it in action
One of 6 test cases the skill fixed. Same model, same prompt, with and without the skill.
1 of 6
Prompt
We are in Phase 2 (bulk data migration) of cutover. After 30 minutes, our migration batch processing shows a 0.8% record failure rate, but the engineer wants to push through since 99.2% succeeded. What quantitative threshold governs the Phase 2 abort decision, and what is the rollback action?
What was checked, without and with the skill
Checked
Without skill
With skill
Defines an explicit data migration error rate threshold of 0.5 percent that mandates an abort if exceeded.
Missed
Passed
Specifies dropping the partially migrated target dataset upon Phase 2 abort.
Passed
Passed
case-14 · gemini-3.6-flash · 8/30/2026 · answers are capped and redacted
What's inside
The instructions your model reads when the skill loads.
SKILL.md204 lines3 files
Guidewire Migration and Upgrade
Overview
Move a Guidewire deployment without losing policies, claims, integrations, or trust. Two related but distinct workflows:
Migration: on-prem InsuranceSuite → Guidewire Cloud (or one cloud tenant → another). Different infrastructure, different config-layer assumptions, different API surfaces.
Upgrade: in-place version bump (e.g., release 202403 → 202503). Same infrastructure, new code, new APIs, deprecated APIs to retire.
Both are heavy lifts that go badly if executed without rehearsal. Five production failures this skill prevents:
Config reconciliation gaps — on-prem carries 5 years of customizations; cloud tenant ships with newer base config; cutover deploys the on-prem config and breaks because base assumptions diverged.
Deprecated-API blind spots — version upgrade removes a Cloud API that an integration depended on; the integration starts returning 404 the moment the upgrade lands.
No mid-flight rollback — cutover starts at midnight, fails at 2am, decision is "abort or push through"; without a pre-defined abort path the team chooses badly.
Data migration that loses optimistic-locking history — claims migrate but checksum values do not; downstream integrations fail every PATCH for a week until checksums regenerate.
Communication misalignment — brokers told "use the new system Monday" while the old system is still authoritative for in-flight quotes; bound state lives in two systems.
Prerequisites
Approved migration / upgrade plan with named owners for: config reconciliation, data migration, integration cutover, communication, rollback authorization
A staging tenant on the target platform (cloud) or target version that is exact-replica of production minus customer data
Production-shape sample dataset for rehearsal (anonymized but representative volumes and shapes)
Cutover window scheduled with documented blackout period for non-essential changes
For upgrades: Guidewire's release notes for every version between current and target; deprecated API list for the target release
Instructions
Build the migration / upgrade plan in this order. Each step targets one of the five production failures listed in Overview.
1. Inventory the current state
Before designing the move, know what is actually deployed:
Surface
Catalog
Custom Gosu code
every file under modules/configuration/gsrc/; commit count, author distribution
Custom plugins
every entry in plugin/registry/*.xml
Custom entity extensions
every .eti file deviation from base
Outbound integrations
every Service Application registered in GCC; their roles and endpoints called
Inbound integrations
every messaging destination consuming App Events; their delivery destinations
Lock down a Guidewire Cloud API integration so it survives a SOC 2 audit, an NAIC Model Audit Rule review, and a real-world incident — least-privilege role design, encrypted committed secrets via SOPS+age, PII redaction in logs (SSN/DOB/claim narrative), audit-trail capture, cross-tenant isolation for multi-carrier integrations, and detect-and-rotate response to token leaks. Use when designing the security posture for a new integration, hardening an existing one before audit, or responding to a