Agent skill

Guidewire Migration And Upgrade

by jeremylongshore in jeremylongshore/tons-of-skills-marketplace

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)…

MITAuto-check passedDevOps & Cloud

Install Guidewire Migration And Upgrade

skills CLI
$ npx skills add jeremylongshore/tons-of-skills-marketplace --skill guidewire-migration-and-upgrade -a claude-code

Project install by default; add -g for ~/.claude/skills/.

GitHub CLI
$ gh skill install jeremylongshore/tons-of-skills-marketplace guidewire-migration-and-upgrade --agent claude-code

Project scope by default; add --scope user for a personal install. Needs GitHub CLI 2.90.0 or later (public preview).

Manual copy
$ git clone --depth 1 https://github.com/jeremylongshore/tons-of-skills-marketplace.git skills-src && mkdir -p .claude/skills && cp -r skills-src/skills/.curated/guidewire-migration-and-upgrade .claude/skills/guidewire-migration-and-upgrade && rm -rf skills-src

Use ~/.claude/skills/ instead of .claude/skills for a personal install. The folder must contain SKILL.md.

Claude Code skills documentation · loads skills from .claude/skills/

Facts

Skill name
guidewire-migration-and-upgrade
GitHub stars
2.8k
Token cost
~3.5k tokens
SKILL.md length
1,411 words
Files
3 (incl. references)
Skills in repo
3,342
Repo updated
First seen
Licence
MIT

At a glance

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)…

  • Works in 7 steps: Inventory the current state → Reconcile against the target → Design the data migration plan → …
  • Planning a cloud migration
  • SKILL.md covers Overview, Prerequisites, Instructions and Output, plus 4 more sections
  • Calls curl, jq and psql

What it does

Guidewire Migration And Upgrade is an agent skill from jeremylongshore/tons-of-skills-marketplace. 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. Use when planning a cloud migration, executing a version upgrade, or rehearsing a cutover. Trigger…

Its SKILL.md is about 3.5k tokens, which your agent loads only when the skill is triggered. The skill folder holds 3 other files, including reference files (for example `references/API_REFERENCE.md` and `references/implementation-guide.md`). Compatibility notes: Designed for Claude Code

It sits in DevOps & Cloud, covering Code migrations, Accounting and bookkeeping and Cloud architecture. The repository describes itself as: Model-agnostic agent-skills platform with a harness-free canonical layer, verified adapters, and the ccpi package manager. Explore at tonsofskills.com. The licence is MIT.

When your agent uses it

  • Planning a cloud migration
  • Executing a version upgrade
  • Rehearsing a cutover
  • With guidewire migration

Example prompts

  • “guidewire migration”
  • “guidewire upgrade”
  • “guidewire cutover”
  • “/guidewire-migration-and-upgrade”

Requirements

  • Compatibility (from SKILL.md): Designed for Claude Code
  • Pre-approved tools (allowed-tools): Read, Write, Edit, Bash(gradle:*), Bash(curl:*), Bash(jq:*), Bash(diff:*), Grep, Glob

Workflow steps

7 steps, taken from the step headings in SKILL.md.

  1. Inventory the current state
  2. Reconcile against the target
  3. Design the data migration plan
  4. Rehearse end-to-end
  5. Cutover with mid-flight abort path
  6. Post-cutover rollback (rare, hard)
  7. Communicate aggressively

What it can do on your machine

Read from SKILL.md and the folder at commit cfae287. It shows what the files ask for, not the result of running them.

  • Tool permissions

    Pre-approves these tools, so the agent can use them without asking each time:

    • Read
    • Write
    • Edit
    • Bash(gradle:*)
    • Bash(curl:*)
    • Bash(jq:*)
    • Bash(diff:*)
    • Grep
    • Glob

    From allowed-tools in the SKILL.md frontmatter.

  • Runs code

    Shell commands in SKILL.md call:

    • curl
    • jq
    • psql

    From the folder's file list and the shell code blocks in SKILL.md.

  • Network

    Links to these hosts (documentation or services it may open):

    • docs.guidewire.com
    • martinfowler.com

    From URLs in SKILL.md, links to its own repository left out.

  • Credentials

    Names no API keys, tokens, secrets or passwords.

    From names ending in _API_KEY, _TOKEN, _SECRET, _KEY or _PASSWORD in SKILL.md.

  • Compatibility

    Designed for Claude Code

    From compatibility in the SKILL.md frontmatter.

Context cost

Guidewire Migration And Upgrade loads about 3.5k tokens when it runs, and up to ~7.1k if it reads all its reference files. Until then it costs about 167 tokens; SKILL.md has 1,411 words of instructions outside code blocks.

Always · name and description, kept in context so the agent knows when to use it
~167
When it runs · the whole SKILL.md, loaded when a task matches
~3.5k
With references · SKILL.md plus every file in references/, read only if the agent opens them
~7.1k

Estimates: characters ÷ 4, the usual rule of thumb; real counts depend on the model's tokenizer. Scripts and assets cost tokens only if the agent reads them.

Safety

Auto-check passed

The automated check found no risky patterns in SKILL.md.

Automated static check — not a guarantee. Review scripts before installing. It scans the text of SKILL.md for risky patterns (piping downloads into a shell, reading credential files, hidden Unicode, destructive commands); files beside SKILL.md are not scanned.

SKILL.md

The full file from jeremylongshore/tons-of-skills-marketplace at commit cfae287, republished under its MIT licence (© jeremylongshore). 1,411 words, ~3,548 tokens.

Download SKILL.mdSave it as .claude/skills/guidewire-migration-and-upgrade/SKILL.md (or your agent's skills folder). This skill also uses 2 other files; get the full folder from GitHub.
name
guidewire-migration-and-upgrade
description
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. Use when planning a cloud migration, executing a version upgrade, or rehearsing a cutover. Trigger with "guidewire migration", "guidewire upgrade", "guidewire cutover", "guidewire on-prem to cloud", "202503 upgrade".
allowed-tools
Read, Write, Edit, Bash(gradle:*), Bash(curl:*), Bash(jq:*), Bash(diff:*), Grep, Glob
compatibility
Designed for Claude Code
version
1.26.0
license
MIT
author
Jeremy Longshore <jeremy@intentsolutions.io>
tags
guidewire, migration, upgrade, cutover, cloud, rehearsal

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:

  1. 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.
  2. 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.
  3. 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.
  4. 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.
  5. 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:

SurfaceCatalog
Custom Gosu codeevery file under modules/configuration/gsrc/; commit count, author distribution
Custom pluginsevery entry in plugin/registry/*.xml
Custom entity extensionsevery .eti file deviation from base
Outbound integrationsevery Service Application registered in GCC; their roles and endpoints called
Inbound integrationsevery messaging destination consuming App Events; their delivery destinations
Reports and queriesdashboards, scheduled batch jobs, ad-hoc Gosu Query API uses
Custom UI / PCFevery PCF file deviation from base

The inventory drives reconciliation. Skipping it is how 30-month "migration" projects happen — surprise customizations surface every other week.

2. Reconcile against the target

For migrations: identify each customization's status against the cloud base config (still applicable / superseded by base / requires re-implementation / no longer needed). For upgrades: identify each customization's status against the target version's base config.

Custom file          Base file (target)         Status
gsrc/.../UWRule1.gs  same path, same hash       no-op (carrier kept it through upgrade)
gsrc/.../UWRule2.gs  same path, different hash  manual merge required
gsrc/.../UWRule3.gs  not present in target      cut by Guidewire; verify if rule still needed
                     gsrc/.../NewRule.gs        new in target; no carrier override needed

Use diff -r between current and target base config zones; the output is the merge backlog. Each row gets an owner and a target completion date.

3. Design the data migration plan

For migrations between deployments, every entity needs to move. The non-obvious challenges:

  • Foreign-key resolution: claim.Policy is a reference to a Policy resource id; new tenant assigns new ids; mapping table required.
  • Checksum continuity: Cloud API uses checksum for optimistic locking; migration must populate plausible checksums or downstream PATCH calls fail until they refresh through GET-then-PATCH.
  • Audit log retention: regulatory requirement to retain claim-state history; the old system's audit log must migrate or be archived in a regulator-acceptable format.
  • Document attachments: claim photos, declaration pages, evidence; can be GBs per claim; needs separate transfer plan.
  • In-flight resources: submissions in Quoted, claims in Open; cutover plan must decide: complete in old, suspend through cutover, or recreate in new.

A typical large-tenant migration moves 100M+ entity rows; rehearsal at production scale (or close to it) is non-negotiable.

4. Rehearse end-to-end

Before the real cutover, run the full migration against the staging environment with production-shape data. Measure:

  • Total wall-clock time of data migration
  • Per-entity throughput
  • Failure rate per entity type
  • Post-migration reachability check (every integration's first call works against the new system)
  • Time to roll back if abort triggered at each phase

A first rehearsal failing somewhere is normal and expected; the second rehearsal failing somewhere is also normal; the third rehearsal failing somewhere means the plan has gaps. Do not cut over from a third-failure plan.

5. Cutover with mid-flight abort path

The cutover is a sequence of phases, each with a defined abort point:

Phase 0: Quiesce — pause non-essential writes; communicate to brokers.        [ABORT: resume; reschedule]
Phase 1: Snapshot — capture point-in-time of source.                           [ABORT: discard snapshot]
Phase 2: Migrate data — bulk move per the data plan.                           [ABORT: drop staging; resume source]
Phase 3: Cut integrations — repoint downstream systems to new tenant.          [ABORT: revert integration config]
Phase 4: Validate — run smoke tests + spot-check 100 random policies.          [ABORT: revert integrations + consider replay]
Phase 5: Open — accept production writes on new tenant.                        [ABORT: difficult; requires rollback plan from §6]
Phase 6: Decommission window — keep source read-only for 30 days for audit.    [ABORT: not applicable; cutover complete]

The abort criterion at each phase is a quantitative threshold (data migration error rate > 0.5%, smoke test failure on >10 of 100 spot checks, etc.) decided in advance, not improvised at 2am. Each abort path has a documented runbook.

6. Post-cutover rollback (rare, hard)

After Phase 5, the new system is authoritative. Rollback after this point is genuinely hard because writes have happened on the new tenant that did not happen on the old. Two options:

  • Forward fix: keep new tenant; fix issues in place. Always preferred when possible.
  • Reverse migration: replay writes from new tenant back to old. Possible only if the cutover preserved a write-audit log on the new side; absent that, data is lost.

Document the cutoff time after which forward fix is the only option (typically Phase 5 + 1 hour). Past that line, communicate honestly to stakeholders about what is and is not recoverable.

Show full SKILL.md (544 more words)Show less
7. Communicate aggressively

Stakeholders to brief, in priority order:

StakeholderWhenContent
Underwriting + claims operationsT-30 dayswhat changes, what stays the same, training schedule
Broker networkT-14 daysURL changes, login changes, transition for in-flight quotes
Claimants with open claimsT-7 daysclaim numbers stable; new portal URL
State insurance regulatorsper regulatory requirementsNAIC notification if applicable
Internal IT / securityT-14 daysnew tenant URLs for firewall, new audit log location

Crucially: the message includes the cutover timing and what to do if something looks wrong. Brokers panicking at 9am Monday because they cannot log in to the old URL is preventable.

Output

A migration / upgrade ships with all of the following:

  • A complete inventory of customizations, integrations, and dependencies, owned and dated.
  • A reconciliation document mapping every customization to its disposition against the target.
  • A data migration plan with foreign-key resolution, checksum strategy, audit-log retention, document-attachment transfer, and in-flight resource handling.
  • ≥3 successful end-to-end rehearsals against staging at production scale.
  • A cutover runbook with phase-by-phase abort criteria and pre-written abort runbooks.
  • A post-cutover monitoring plan with elevated alert thresholds for the first 7 days.
  • Stakeholder communication delivered on the T-30 / T-14 / T-7 / T-0 schedule.

Examples

Example 1 — Customization inventory diff
bash
# diff carrier's current config zone against target version's base
diff -r --brief \
  ~/projects/policycenter-202403/modules/configuration \
  ~/projects/policycenter-202503-base/modules/configuration \
  > customizations.txt
# Each "Files differ" line is a customization to reconcile
Example 2 — Phase-2 abort criterion
yaml
phase: data-migration
abort_if:
  - error_rate > 0.005           # 0.5% failure rate
  - throughput < 1000_per_min    # falling behind cutover window budget
  - source_DB_read_lag > 60s     # source replication broken
on_abort:
  - drop_staging_dataset()
  - re-enable_source_writes()
  - notify_stakeholders("data migration aborted; investigation in progress")
Example 3 — Smoke-test spot check (Phase 4)
bash
# Pick 100 random policies; verify they read identically from new tenant
psql -tAc "SELECT policy_number FROM policies ORDER BY random() LIMIT 100" \
  | while read -r policy; do
      OLD=$(curl -fsS $OLD_PC/policies?policyNumber=$policy | jq '.data[0].attributes.totalPremium')
      NEW=$(curl -fsS $NEW_PC/policies?policyNumber=$policy | jq '.data[0].attributes.totalPremium')
      [ "$OLD" = "$NEW" ] || echo "DRIFT: $policy old=$OLD new=$NEW"
    done

If >10 drifts in the 100 sample, abort. Below that, accept and document the drift cases for forward fix.

Error Handling

SymptomCauseSolution
Customization inventory missing filesnon-tracked Gosu, untracked plugin entriescheck filesystem, not just git; some carriers have local-only customizations
Reconciliation step says "manual merge" for many filesbase config diverged significantly across versionsbudget more time; consider a phased upgrade through intermediate versions
Data migration throughput drops below plansource-DB read contention, network bottleneck, or staging-DB write contentionidentify bottleneck before cutover; cutover-day surprises mean abort
Spot-check shows premium drift on a sample policyrate plan migrated incorrectly or rule code differs in targetabort and investigate; do not accept "minor drift" — the next 100 spot checks will compound
Mid-cutover network partitioninfrastructure issue independent of the migrationif Phase ≤2 detected: abort. If Phase ≥3: depends on partition extent — partial cutover is the worst state
Phase-5 production traffic showing 5xxintegration cutover incomplete or new tenant's auth not yet primedenacted abort plan if past Phase 5 + 1h is unrealistic; usually forward-fix
Brokers calling support saying "can't log in"comms went out late or pointed at wrong URLaccept the goodwill cost; communicate the corrected URL; do not blame brokers
Audit log retention from old tenant lostmigration plan did not address itregulatory issue; retain a snapshot in cold storage and document for next audit

For deeper coverage (Migration Accelerator usage, parallel-run validation, blue-green migration tenant patterns, regulatory notification requirements per state), see implementation guide and API reference.

See Also

  • guidewire-ci-cd-pipeline — the deploy substrate that promotes the migrated config to the new tenant
  • guidewire-install-auth — the new tenant's auth setup; secrets rotation across the cutover
  • guidewire-sdk-patterns — checksum continuity considerations for migrated data
  • guidewire-observability-and-incident-response — elevated-threshold monitoring during the post-cutover stabilization window
  • guidewire-webhooks-integrations — App Event consumer cutover; potentially replay events from migration window

Resources

© jeremylongshore, MIT. Rendered from Markdown: HTML in the file is shown as text, images as links, and headings moved down two levels. Raw file

Files

SKILL.md and 2 other files (references) in skills/.curated/guidewire-migration-and-upgrade of jeremylongshore/tons-of-skills-marketplace.

  • SKILL.md
  • references/API_REFERENCE.md
  • references/implementation-guide.md

Open the folder on GitHubat commit cfae287

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Questions about Guidewire Migration And Upgrade

What does Guidewire Migration And Upgrade do?

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)…. Guidewire Migration And Upgrade is an agent skill from jeremylongshore/tons-of-skills-marketplace., 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.

When should I use Guidewire Migration And Upgrade?

Guidewire Migration And Upgrade fits situations like: planning a cloud migration; executing a version upgrade; rehearsing a cutover; with guidewire migration.

How do I install Guidewire Migration And Upgrade in Claude Code?

Run `npx skills add jeremylongshore/tons-of-skills-marketplace --skill guidewire-migration-and-upgrade -a claude-code`. Or copy the skill folder (skills/.curated/guidewire-migration-and-upgrade in jeremylongshore/tons-of-skills-marketplace) into .claude/skills/guidewire-migration-and-upgrade in your project. Claude Code loads it when a task matches its description.

How do I install Guidewire Migration And Upgrade in Codex?

Run `npx skills add jeremylongshore/tons-of-skills-marketplace --skill guidewire-migration-and-upgrade -a codex`. Or copy the skill folder (skills/.curated/guidewire-migration-and-upgrade in jeremylongshore/tons-of-skills-marketplace) into .agents/skills/guidewire-migration-and-upgrade in your project. Codex loads it when a task matches its description.

Can I use Guidewire Migration And Upgrade in Cursor, Gemini CLI or GitHub Copilot?

Cursor, Gemini CLI, GitHub Copilot and OpenCode also load SKILL.md folders. With the skills CLI, run `npx skills add jeremylongshore/tons-of-skills-marketplace --skill guidewire-migration-and-upgrade -a cursor` (or -a gemini-cli, github-copilot or opencode for the others). To copy it by hand, put the folder in .cursor/skills/guidewire-migration-and-upgrade, .gemini/skills/guidewire-migration-and-upgrade, .github/skills/guidewire-migration-and-upgrade and .opencode/skills/guidewire-migration-and-upgrade in your project.

What does Guidewire Migration And Upgrade need to run?

Going by SKILL.md and its folder, Guidewire Migration And Upgrade needs the command-line tools its instructions call (curl, jq and psql). Its frontmatter pre-approves these tools: Read, Write, Edit, Bash(gradle:*), Bash(curl:*), Bash(jq:*), Bash(diff:*), Grep, Glob. Compatibility (from SKILL.md): Designed for Claude Code.

Does Guidewire Migration And Upgrade access the network?

SKILL.md names 2 domains. As links in the text: docs.guidewire.com and martinfowler.com. This is read from the text; nothing was executed.

Is Guidewire Migration And Upgrade safe to install?

Our automated static check of SKILL.md found no risky patterns, such as piping downloads into a shell, reading credential files or hidden Unicode. It is not a guarantee. Review the folder before installing.

What licence does Guidewire Migration And Upgrade use?

Guidewire Migration And Upgrade is published under the MIT licence (declared in SKILL.md). It allows redistribution, so the full SKILL.md is shown on this page.

How many tokens does Guidewire Migration And Upgrade use?

About 3.5k tokens (SKILL.md is roughly 14k characters). Agents keep only the skill's name and description in context until a task matches; then they load SKILL.md in full. Its references folder adds about 3.6k tokens, read only when the agent opens those files.

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Who maintains Guidewire Migration And Upgrade?

jeremylongshore (a GitHub user) maintains it in jeremylongshore/tons-of-skills-marketplace, which has 2,827 GitHub stars. The repository holds 3,342 skills in this directory. The repository was last updated on October 10, 2026.

Source: jeremylongshore/tons-of-skills-marketplace on GitHub. Facts on this page come from the repository at the commit we read; the author's words are quoted as theirs.