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Upgrades Python pip/poetry/pipenv dependencies with breaking change handling

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SKILL.md

name ln-713-pip-upgrader
description Upgrades Python pip/poetry/pipenv dependencies with breaking change handling

ln-713-pip-upgrader

Type: L3 Worker Category: 7XX Project Bootstrap Parent: ln-710-dependency-upgrader

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

See diagram.html for visual 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Phases: Pre-flight → Detect Manager → Security Audit → Check Outdated → Apply Upgrades → Verify Installation → Report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)

Workers assume coordinator (ln-710) already verified git state and created backup.


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Phase 3: Check Outdated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pip pip list --outdated --format=json
poetry poetry show --outdated
pipenv pipenv update --outdated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 <package>
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:

  • "<package> python <version> breaking changes migration"
  • "<ImportError message> <package> fix"

Phase 5: Verify Installation

Commands

Check Command
Import test python -c "import <package>"
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

See 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


Version: 1.1.0 Last Updated: 2026-01-10