Paths: File paths ( shared/ , references/ , ../ln-* ) are relative to skills repo root. If not found at CWD, locate this SKILL.md directory and go up one level for repo root. ln-823-pip-upgrader Type: L3 Worker Category: 8XX Optimization Parent: ln-820-dependency-optimization-coordinator Upgrades Python dependencies with automatic breaking change detection. Overview Aspect Details Input Project path, package manager type Output Updated requirements.txt/pyproject.toml Supports pip, poetry, pipenv Workflow Phases: Pre-flight → Detect Manager → Security Audit → Check Outdated → Apply Upgrades → Verify Installation → Report Phase 0: Pre-flight Checks Check Required Action if Missing requirements.txt OR pyproject.toml OR Pipfile Yes Block upgrade Virtual environment active No Warn user (risk of system pollution) Git clean state Yes Block (need clean baseline for revert) Workers assume coordinator (ln-820) already verified git state and created backup. Worktree & Branch Isolation MANDATORY READ: Load shared/references/git_worktree_fallback.md — use ln-823 row. Phase 1: Detect Manager Manager Indicator Files pip requirements.txt poetry pyproject.toml + poetry.lock pipenv Pipfile + Pipfile.lock Phase 2: Security Audit Commands Manager Command pip pip-audit --json poetry poetry audit (via plugin) pipenv pipenv check Actions Severity Action Critical Block upgrade, report High Warn, continue Moderate/Low Log only Phase 3: Check Outdated Commands Manager Command pip pip list --outdated --format=json poetry poetry show --outdated pipenv pipenv update --outdated Phase 4: Apply Upgrades Commands Manager Command pip pip install --upgrade pip (freeze) pip freeze > requirements.txt poetry poetry update pipenv pipenv update MCP Tools for Migration Search Priority Order (Fallback Strategy) Priority Tool When to Use 1 mcp__context7__query-docs First choice for library docs 2 mcp__Ref__ref_search_documentation Official docs and PyPI 3 WebSearch Latest info, community solutions Context7 Usage Step Tool Parameters 1. Find library mcp__context7__resolve-library-id libraryName: "pydantic" 2. Query docs mcp__context7__query-docs query: "pydantic v1 to v2 migration breaking changes" MCP Ref Usage Action Tool Query Example Search mcp__Ref__ref_search_documentation "python pydantic 2 migration guide" Read mcp__Ref__ref_read_url URL from search results WebSearch Fallback Use when Context7/Ref return no results: " python breaking changes migration" " fix" Phase 5: Verify Installation Commands Check Command Import test python -c "import " Tests pytest or python -m pytest Phase 6: Report Results Report Schema Field Description project Project path packageManager pip, poetry, or pipenv duration Total time upgrades[] Applied upgrades verification PASSED or FAILED Common Breaking Changes MANDATORY READ: Load breaking_changes_patterns.md for full patterns. Package Breaking Version Key Changes pydantic 1 → 2 V1 compatibility layer needed sqlalchemy 1 → 2 Query syntax changes fastapi 0.99 → 0.100+ Pydantic v2 required Configuration Options :

Upgrade scope

upgradeType : major

major | minor | patch

Security

auditLevel : high minimumReleaseAge : 14

Python specific

pythonVersion : "3.12" useVirtualenv : true

Verification

runTests : true Error Handling Error Cause Solution ImportError Breaking API change Search Context7/Ref for migration Dependency conflict Version mismatch Try pip-compile or poetry lock References breaking_changes_patterns.md python_venv_handling.md Definition of Done Package manager detected (pip/poetry/pipenv) from indicator files Security audit completed (pip-audit/poetry audit/pipenv check) Outdated packages identified and listed Upgrades applied with requirements.txt/pyproject.toml updated Breaking changes handled via MCP migration guides Import tests and pytest pass after upgrades Report returned with upgrades applied and verification status Version: 1.1.0 Last Updated: 2026-01-10