skills/secondsky/claude-skills/dependency-upgrade

dependency-upgrade

Installation
SKILL.md

Dependency Upgrade

Manage dependency upgrades with supply chain security, compatibility analysis, staged rollout, and comprehensive testing across all major package managers.

When to Use This Skill

  • Upgrading major framework or library versions
  • Configuring supply chain attack prevention (cooldown, script blocking, lockfile hardening)
  • Setting up secure package manager configuration
  • Resolving dependency conflicts or peer dependency issues
  • Planning incremental upgrade paths with testing
  • Automating dependency updates with Renovate, Dependabot, or Snyk
  • Auditing dependencies for vulnerabilities
  • Setting up CI/CD dependency security workflows

Two Modes of Operation

Interactive — Walk through setup questions to generate tailored config. Use for fresh setup.

Default — Apply recommended defaults immediately: 7-day cooldown, block all scripts, frozen-lockfile, lockfile-lint, Dependabot with cooldown. Customization optional.

Interactive Setup Flow

When the user wants tailored configuration, walk through these decisions. Skip this section entirely if using default mode.

Tier 1: Required Decisions

Always ask these 3 questions before generating any config:

1. Package Manager

"Which package manager does this project use?"

Answer Generates
npm .npmrc
Bun bunfig.toml
pnpm pnpm-workspace.yaml
Yarn .yarnrc.yml
Deno deno.json config

2. Cooldown Period

"How many days should newly published packages age before install? This prevents supply chain attacks where malicious packages are discovered and unpublished within days."

Option Days Use Case
Aggressive 3 Catches most typosquatting
Recommended 7 Good balance for most projects
Conservative 14 Critical/production systems
Paranoid 21 Matches Snyk's built-in default
Custom N User specifies

3. Post-Install Script Policy

"How should lifecycle scripts (postinstall, preinstall) be handled? These are the #1 attack vector for supply chain attacks."

Option Behavior
Block all (recommended) --ignore-scripts + allow-git=none
Allowlist Block by default, allow specific trusted packages
Review only Warn but don't block

Tier 2: Security Tooling (Offer as Batch)

"Which of these security features would you like to configure? Select any that apply."

4. CI/CD Automation Tool

Answer Generates
Dependabot .github/dependabot.yml with cooldown
Renovate renovate.json with minimumReleaseAge
Snyk No config needed (21-day cooldown built-in)
None Skip

5. Automerge Policy

Option Behavior
None All updates require manual review
Minor+Patch only Auto-merge safe updates, review majors
All with approval Auto-merge after team approval

6. Update Schedule

Option Config Value
Daily "daily"
Weekly (default) "weekly"
Biweekly "biweekly"
Monthly "monthly"

7. Install-Time Auditing

Option Installs
npq Pre-install package auditor (open source)
Socket Firewall (sfw) Real-time malicious package blocker
Both Both tools with shell aliases
None Skip

8. Lockfile Validation

Option Behavior
Yes (recommended) Adds lockfile-lint + CI script
No Skip

Tier 3: Advanced Options (Only If User Opts In)

"Would you like to configure any advanced options?"

9. Dev Containers — Generate hardened .devcontainer/devcontainer.json (Yes/No)

10. Secrets Manager — 1Password CLI / Infisical / None

11. pnpm Trust Policy — Enable trustPolicy: no-downgrade (pnpm 10.21+ only, Yes/No)

12. Cooldown Exclusions — Package names that bypass cooldown (e.g., @types/react, typescript, esbuild)

Security-First Upgrade Principles

  1. Cooldown before installing — Wait 7 days for new package versions to be vetted by the community
  2. Block post-install scripts — Prevent arbitrary code execution during npm install
  3. Freeze lockfiles in CI — Use deterministic installs (npm ci, --frozen-lockfile)
  4. Validate lockfile integrity — Use lockfile-lint to detect injection
  5. Audit before trusting — Use npq or sfw to check packages before installing
  6. Upgrade incrementally — One major version at a time with testing between each
  7. Never blindly upgrade — Avoid npm update or npm-check-updates -u without review

Cooldown Period: Prevent Supply Chain Attacks

Newly published packages may contain malicious code discovered within hours. Configure a cooldown period to delay installation.

Quick Setup

npm (.npmrc):

min-release-age=7

Bun (bunfig.toml):

[install]
minimumReleaseAge = 604800  # 7 days in seconds
minimumReleaseAgeExcludes = ["@types/bun", "typescript"]

pnpm (pnpm-workspace.yaml):

minimumReleaseAge: 10080  # 7 days in minutes
minimumReleaseAgeExclude:
  - '@types/react'
  - typescript

Yarn (.yarnrc.yml):

npmMinimalAgeGate: "7d"
npmPreapprovedPackages:
  - "@types/react"
  - "typescript"

Load references/cooldown-config-guide.md for detailed per-PM configuration, CI tool integration, and exclusion patterns.

Use templates/<pm>-security.tmpl for copy-paste ready config files.

Disable Post-Install Scripts

Post-install scripts are the most common supply chain attack vector (Shai-Hulud, Nx, event-stream incidents).

Quick Setup

npm:

npm config set ignore-scripts true
npm config set allow-git none

Bun: Disabled by default. Allow specific packages in package.json:

{ "trustedDependencies": ["esbuild", "sharp"] }

pnpm (10.0+): Disabled by default. Allow specific packages in pnpm-workspace.yaml:

allowBuilds:
  esbuild: true
strictDepBuilds: true  # Hard error on unreviewed scripts

Load references/package-manager-security.md for full per-PM hardening including pnpm trustPolicy, blockExoticSubdeps, and @lavamoat/allow-scripts.

Deterministic & Frozen Installs

Always use frozen install commands in CI to ensure reproducible builds:

Package Manager Command What It Does
npm npm ci Deletes node_modules, installs exact lockfile versions
Bun bun install --frozen-lockfile Fails if lockfile is out of sync
pnpm pnpm install --frozen-lockfile Fails if lockfile is out of sync
Yarn yarn install --immutable --immutable-cache Validates lockfile and cache
Deno deno install --frozen Frozen installation

Commit all lockfiles to version control: package-lock.json, bun.lock, pnpm-lock.yaml, yarn.lock, deno.lock.

Lockfile Validation

Install and configure lockfile-lint to detect lockfile injection attacks:

npm install --save-dev lockfile-lint
{
  "scripts": {
    "lint:lockfile": "lockfile-lint --path package-lock.json --type npm --allowed-hosts npm --validate-https",
    "preinstall": "npm run lint:lockfile"
  }
}

Note: lockfile-lint does not currently support Bun's bun.lock / bun.lockb formats.

Pre-Install Security Auditing

npq — Pre-Install Auditor

npm install -g npq
npq install <package>          # Audit before installing
npq install <package> --dry-run # Audit without installing

# Shell alias for seamless use
alias npm='npq-hero'

# Use with other PMs
NPQ_PKG_MGR=pnpm npq install <package>
NPQ_PKG_MGR=bun npq install <package>

Socket Firewall (sfw) — Real-Time Blocker

npm install -g sfw
sfw npm install <package>      # Blocks malicious packages
sfw pnpm add <package>
sfw yarn add <package>

Load references/supply-chain-security.md for full comparison of npq vs sfw and what each validates.

Dependency Analysis

# Audit for vulnerabilities
bun audit       # Bun
npm audit       # npm
yarn audit      # Yarn

# Check for outdated packages
bun outdated
npm outdated

# Interactive upgrade (safe — review each)
bunx npm-check-updates --interactive

# Analyze dependency tree
npm ls <package-name>
yarn why <package-name>

Staged Upgrade Strategy

Upgrade one dependency at a time with testing between each:

# 1. Create feature branch
git checkout -b upgrade/<package>-<version>

# 2. Upgrade single package
bun add <package>@<version>

# 3. Test immediately
bun test && bunx tsc --noEmit && bun run build

# 4. Commit and continue
git add -A && git commit -m "chore: upgrade <package> to <version>"

Load references/staged-upgrades.md for codemod automation, custom migration scripts, and peer dependency handling.

Load references/compatibility-matrix.md for version compatibility tables (React 18/19, Next.js 13-15, TypeScript, Tailwind 3/4).

Automated Updates with Cooldown

Configure CI/CD tools to respect cooldown periods:

Dependabot (.github/dependabot.yml)

version: 2
updates:
  - package-ecosystem: "npm"
    directory: "/"
    schedule:
      interval: "weekly"
    cooldown:
      default-days: 7

Renovate (renovate.json)

{
  "extends": ["config:base"],
  "minimumReleaseAge": "7 days",
  "packageRules": [
    {
      "matchUpdateTypes": ["minor", "patch"],
      "automerge": true
    },
    {
      "matchUpdateTypes": ["major"],
      "automerge": false,
      "minimumReleaseAge": "14 days"
    }
  ]
}

Snyk

Snyk includes a built-in 21-day cooldown for upgrade PRs. No configuration needed.

Use templates/dependabot-security.tmpl or templates/renovate-security.tmpl for complete config files.

Publishing Security

For package maintainers:

# Enable 2FA
npm profile enable-2fa auth-and-writes

# Publish with provenance (cryptographic build proof)
npm publish --provenance

# Trusted publishing via OIDC (eliminates long-lived tokens)
# Configure on npmjs.com, then:
# In GitHub Actions: permissions: id-token: write

Load references/supply-chain-security.md for full publishing security guide including OIDC setup and dependency tree reduction.

Dev Environment Hardening

Isolate dependency execution from the host system:

  • Dev containers — limit blast radius of malicious packages
  • Secrets management — use 1Password CLI or Infisical instead of plaintext .env files
  • Dependency tree reduction — replace common packages with native JS

Use templates/devcontainer-security.tmpl for a hardened dev container config.

Load references/secrets-and-containers.md for dev container setup, secrets management, and dependency reduction patterns.

Testing Strategy

Run tests at every level after each upgrade:

# 1. Static analysis (fastest)
bunx tsc --noEmit && bun run lint

# 2. Unit tests
bun test

# 3. Build check
bun run build

# 4. Integration / E2E (after major upgrades)
bun run test:e2e

Load references/testing-strategy.md for full testing pyramid, CI integration, and bundle analysis.

Rollback Plan

#!/bin/bash
git stash
git checkout -b upgrade/<package>

bun add <package>@latest

if bun test && bun run build; then
  git add package.json bun.lock
  git commit -m "chore: upgrade <package>"
else
  echo "Upgrade failed, rolling back"
  git checkout main
  git branch -D upgrade/<package>
  bun install
fi

Upgrade Checklist

Pre-Upgrade:
- [ ] Review current dependency versions
- [ ] Read changelogs for breaking changes
- [ ] Create feature branch
- [ ] Tag current state (git tag pre-upgrade)
- [ ] Run full test suite (baseline)
- [ ] Verify cooldown period is configured

Security Pre-Checks:
- [ ] Post-install scripts are disabled
- [ ] Lockfile validation is active
- [ ] Install auditing tools configured (if applicable)
- [ ] CI uses frozen-lockfile install

During Upgrade:
- [ ] Upgrade one dependency at a time
- [ ] Respect cooldown period (don't force latest)
- [ ] Update peer dependencies
- [ ] Fix TypeScript errors
- [ ] Run test suite after each upgrade
- [ ] Check bundle size impact

Post-Upgrade:
- [ ] Full regression testing
- [ ] Performance testing
- [ ] Update documentation
- [ ] Deploy to staging
- [ ] Monitor for errors
- [ ] Deploy to production

Common Pitfalls

  • Upgrading all dependencies at once (use incremental upgrades)
  • Blindly running npm update or npm-check-updates -u without review
  • Not testing after each individual upgrade
  • Ignoring peer dependency warnings
  • Forgetting to update or commit the lock file
  • Not reading breaking change notes in changelogs
  • Skipping major versions instead of stepping through them
  • Not having a rollback plan
  • Trusting npmjs.org displayed source code (can differ from actual tarball)
  • Leaving post-install scripts enabled (most common attack vector)
  • Not configuring a cooldown period for new package versions

When to Load References

Load these reference files when the user needs detailed information beyond the quick-reference in SKILL.md:

Load This File When
references/cooldown-config-guide.md Configuring cooldown for a specific PM, CI tool integration, or exclusion patterns
references/package-manager-security.md Full per-PM hardening guide including pnpm trust policy, blockExoticSubdeps, cross-PM cheat sheet
references/supply-chain-security.md Understanding attack vectors, incident history, npq vs sfw comparison, publisher security (2FA, provenance, OIDC)
references/secrets-and-containers.md Setting up dev containers, secrets management with 1Password/Infisical
references/compatibility-matrix.md Checking version compatibility for React, Next.js, TypeScript, Tailwind upgrades
references/staged-upgrades.md Codemod automation, custom migration scripts, peer dependency handling, workspace upgrades
references/testing-strategy.md Full testing pyramid, CI integration, bundle analysis, performance testing

Template Files

Ready-to-use config files in templates/:

Template Purpose
npmrc-security.tmpl Secure .npmrc with scripts disabled + cooldown
bunfig-security.tmpl Secure bunfig.toml with cooldown + exclusions
pnpm-workspace-security.tmpl Secure pnpm-workspace.yaml with cooldown, allowBuilds, trustPolicy
yarnrc-security.tmpl Secure .yarnrc.yml with age gate + preapproved packages
dependabot-security.tmpl Dependabot config with 7-day cooldown
renovate-security.tmpl Renovate config with minimumReleaseAge + automerge rules
devcontainer-security.tmpl Hardened dev container with security options
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