novahiz 0.1.0

package/skills/dependency-auditor/scripts/upgrade_planner.py

@@ -0,0 +1,1029 @@
+#!/usr/bin/env python3
+"""
+Upgrade Planner - Dependency upgrade path planning and risk analysis tool.
+
+This script analyzes dependency inventories, evaluates semantic versioning patterns,
+estimates breaking change risks, and generates prioritized upgrade plans with
+migration checklists and rollback procedures.
+
+Author: Claude Skills Engineering Team
+License: MIT
+"""
+
+import json
+import os
+import sys
+import argparse
+from typing import Dict, List, Set, Any, Optional, Tuple
+from pathlib import Path
+from dataclasses import dataclass, asdict
+from datetime import datetime, timedelta
+from enum import Enum
+import re
+import subprocess
+
+class UpgradeRisk(Enum):
+    """Upgrade risk levels."""
+    SAFE = "safe"
+    LOW = "low"
+    MEDIUM = "medium"
+    HIGH = "high"
+    CRITICAL = "critical"
+
+class UpdateType(Enum):
+    """Semantic versioning update types."""
+    PATCH = "patch"
+    MINOR = "minor"
+    MAJOR = "major"
+    PRERELEASE = "prerelease"
+
+@dataclass
+class VersionInfo:
+    """Represents version information."""
+    major: int
+    minor: int
+    patch: int
+    prerelease: Optional[str] = None
+    build: Optional[str] = None
+    
+    def __str__(self):
+        version = f"{self.major}.{self.minor}.{self.patch}"
+        if self.prerelease:
+            version += f"-{self.prerelease}"
+        if self.build:
+            version += f"+{self.build}"
+        return version
+
+@dataclass
+class DependencyUpgrade:
+    """Represents a potential dependency upgrade."""
+    name: str
+    current_version: str
+    latest_version: str
+    ecosystem: str
+    direct: bool
+    update_type: UpdateType
+    risk_level: UpgradeRisk
+    security_updates: List[str]
+    breaking_changes: List[str]
+    migration_effort: str
+    dependencies_affected: List[str]
+    rollback_complexity: str
+    estimated_time: str
+    priority_score: float
+
+@dataclass
+class UpgradePlan:
+    """Represents a complete upgrade plan."""
+    name: str
+    description: str
+    phase: int
+    dependencies: List[str]
+    estimated_duration: str
+    prerequisites: List[str]
+    migration_steps: List[str]
+    testing_requirements: List[str]
+    rollback_plan: List[str]
+    success_criteria: List[str]
+
+class UpgradePlanner:
+    """Main upgrade planning and risk analysis class."""
+    
+    def __init__(self):
+        self.breaking_change_patterns = self._build_breaking_change_patterns()
+        self.ecosystem_knowledge = self._build_ecosystem_knowledge()
+        self.security_advisories = self._build_security_advisories()
+    
+    def _build_breaking_change_patterns(self) -> Dict[str, List[str]]:
+        """Build patterns for detecting breaking changes."""
+        return {
+            'npm': [
+                r'BREAKING\s*CHANGE',
+                r'breaking\s*change',
+                r'major\s*version',
+                r'removed.*API',
+                r'deprecated.*removed',
+                r'no\s*longer\s*supported',
+                r'minimum.*node.*version',
+                r'peer.*dependency.*change'
+            ],
+            'pypi': [
+                r'BREAKING\s*CHANGE',
+                r'breaking\s*change',
+                r'removed.*function',
+                r'deprecated.*removed',
+                r'minimum.*python.*version',
+                r'incompatible.*change',
+                r'API.*change'
+            ],
+            'maven': [
+                r'BREAKING\s*CHANGE',
+                r'breaking\s*change',
+                r'removed.*method',
+                r'deprecated.*removed',
+                r'minimum.*java.*version',
+                r'API.*incompatible'
+            ]
+        }
+    
+    def _build_ecosystem_knowledge(self) -> Dict[str, Dict[str, Any]]:
+        """Build ecosystem-specific upgrade knowledge."""
+        return {
+            'npm': {
+                'typical_major_cycle_months': 12,
+                'typical_patch_cycle_weeks': 2,
+                'deprecation_notice_months': 6,
+                'lts_support_years': 3,
+                'common_breaking_changes': [
+                    'Node.js version requirements',
+                    'Peer dependency updates',
+                    'API signature changes',
+                    'Configuration format changes'
+                ]
+            },
+            'pypi': {
+                'typical_major_cycle_months': 18,
+                'typical_patch_cycle_weeks': 4,
+                'deprecation_notice_months': 12,
+                'lts_support_years': 2,
+                'common_breaking_changes': [
+                    'Python version requirements',
+                    'Function signature changes',
+                    'Import path changes',
+                    'Configuration changes'
+                ]
+            },
+            'maven': {
+                'typical_major_cycle_months': 24,
+                'typical_patch_cycle_weeks': 6,
+                'deprecation_notice_months': 12,
+                'lts_support_years': 5,
+                'common_breaking_changes': [
+                    'Java version requirements',
+                    'Method signature changes',
+                    'Package restructuring',
+                    'Dependency changes'
+                ]
+            },
+            'cargo': {
+                'typical_major_cycle_months': 6,
+                'typical_patch_cycle_weeks': 2,
+                'deprecation_notice_months': 3,
+                'lts_support_years': 1,
+                'common_breaking_changes': [
+                    'Rust edition changes',
+                    'Trait changes',
+                    'Module restructuring',
+                    'Macro changes'
+                ]
+            }
+        }
+    
+    def _build_security_advisories(self) -> Dict[str, List[Dict[str, Any]]]:
+        """Build security advisory database for upgrade prioritization."""
+        return {
+            'lodash': [
+                {
+                    'advisory_id': 'CVE-2021-23337',
+                    'severity': 'HIGH',
+                    'fixed_in': '4.17.21',
+                    'description': 'Prototype pollution vulnerability'
+                }
+            ],
+            'django': [
+                {
+                    'advisory_id': 'CVE-2024-27351',
+                    'severity': 'HIGH',
+                    'fixed_in': '4.2.11',
+                    'description': 'SQL injection vulnerability'
+                }
+            ],
+            'express': [
+                {
+                    'advisory_id': 'CVE-2022-24999',
+                    'severity': 'MEDIUM',
+                    'fixed_in': '4.18.2',
+                    'description': 'Open redirect vulnerability'
+                }
+            ],
+            'axios': [
+                {
+                    'advisory_id': 'CVE-2023-45857',
+                    'severity': 'MEDIUM',
+                    'fixed_in': '1.6.0',
+                    'description': 'Cross-site request forgery'
+                }
+            ]
+        }
+    
+    def analyze_upgrades(self, dependency_inventory: str, timeline_days: int = 90) -> Dict[str, Any]:
+        """Analyze potential dependency upgrades and create upgrade plan."""
+        dependencies = self._load_dependency_inventory(dependency_inventory)
+        
+        analysis_results = {
+            'timestamp': datetime.now().isoformat(),
+            'timeline_days': timeline_days,
+            'dependencies_analyzed': len(dependencies),
+            'available_upgrades': [],
+            'upgrade_statistics': {},
+            'risk_assessment': {},
+            'upgrade_plans': [],
+            'recommendations': []
+        }
+        
+        # Analyze each dependency for upgrades
+        for dep in dependencies:
+            upgrade_info = self._analyze_dependency_upgrade(dep)
+            if upgrade_info:
+                analysis_results['available_upgrades'].append(upgrade_info)
+        
+        # Generate upgrade statistics
+        analysis_results['upgrade_statistics'] = self._generate_upgrade_statistics(
+            analysis_results['available_upgrades']
+        )
+        
+        # Perform risk assessment
+        analysis_results['risk_assessment'] = self._perform_risk_assessment(
+            analysis_results['available_upgrades']
+        )
+        
+        # Create phased upgrade plans
+        analysis_results['upgrade_plans'] = self._create_upgrade_plans(
+            analysis_results['available_upgrades'],
+            timeline_days
+        )
+        
+        # Generate recommendations
+        analysis_results['recommendations'] = self._generate_upgrade_recommendations(
+            analysis_results
+        )
+        
+        return analysis_results
+    
+    def _load_dependency_inventory(self, inventory_path: str) -> List[Dict[str, Any]]:
+        """Load dependency inventory from JSON file."""
+        try:
+            with open(inventory_path, 'r') as f:
+                data = json.load(f)
+            
+            if 'dependencies' in data:
+                return data['dependencies']
+            elif isinstance(data, list):
+                return data
+            else:
+                print("Warning: Unexpected inventory format")
+                return []
+        
+        except Exception as e:
+            print(f"Error loading dependency inventory: {e}")
+            return []
+    
+    def _analyze_dependency_upgrade(self, dependency: Dict[str, Any]) -> Optional[DependencyUpgrade]:
+        """Analyze upgrade possibilities for a single dependency."""
+        name = dependency.get('name', '')
+        current_version = dependency.get('version', '').replace('^', '').replace('~', '')
+        ecosystem = dependency.get('ecosystem', '')
+        
+        if not name or not current_version:
+            return None
+        
+        # Parse current version
+        current_ver = self._parse_version(current_version)
+        if not current_ver:
+            return None
+        
+        # Get latest version (simulated - in practice would query package registries)
+        latest_version = self._get_latest_version(name, ecosystem)
+        if not latest_version:
+            return None
+        
+        latest_ver = self._parse_version(latest_version)
+        if not latest_ver:
+            return None
+        
+        # Determine if upgrade is needed
+        if self._compare_versions(current_ver, latest_ver) >= 0:
+            return None  # Already up to date
+        
+        # Determine update type
+        update_type = self._determine_update_type(current_ver, latest_ver)
+        
+        # Assess upgrade risk
+        risk_level = self._assess_upgrade_risk(name, current_ver, latest_ver, ecosystem, update_type)
+        
+        # Check for security updates
+        security_updates = self._check_security_updates(name, current_version, latest_version)
+        
+        # Analyze breaking changes
+        breaking_changes = self._analyze_breaking_changes(name, current_ver, latest_ver, ecosystem)
+        
+        # Calculate priority score
+        priority_score = self._calculate_priority_score(
+            update_type, risk_level, security_updates, dependency.get('direct', False)
+        )
+        
+        return DependencyUpgrade(
+            name=name,
+            current_version=current_version,
+            latest_version=latest_version,
+            ecosystem=ecosystem,
+            direct=dependency.get('direct', False),
+            update_type=update_type,
+            risk_level=risk_level,
+            security_updates=security_updates,
+            breaking_changes=breaking_changes,
+            migration_effort=self._estimate_migration_effort(update_type, breaking_changes),
+            dependencies_affected=self._get_affected_dependencies(name, dependency),
+            rollback_complexity=self._assess_rollback_complexity(update_type, risk_level),
+            estimated_time=self._estimate_upgrade_time(update_type, breaking_changes),
+            priority_score=priority_score
+        )
+    
+    def _parse_version(self, version_string: str) -> Optional[VersionInfo]:
+        """Parse semantic version string."""
+        # Clean version string
+        version = re.sub(r'[^0-9a-zA-Z.-]', '', version_string)
+        
+        # Basic semver pattern
+        pattern = r'^(\d+)\.(\d+)\.(\d+)(?:-([0-9A-Za-z.-]+))?(?:\+([0-9A-Za-z.-]+))?$'
+        match = re.match(pattern, version)
+        
+        if match:
+            major, minor, patch, prerelease, build = match.groups()
+            return VersionInfo(
+                major=int(major),
+                minor=int(minor),
+                patch=int(patch),
+                prerelease=prerelease,
+                build=build
+            )
+        
+        # Fallback for simpler version patterns
+        simple_pattern = r'^(\d+)\.(\d+)(?:\.(\d+))?'
+        match = re.match(simple_pattern, version)
+        if match:
+            major, minor, patch = match.groups()
+            return VersionInfo(
+                major=int(major),
+                minor=int(minor),
+                patch=int(patch or 0)
+            )
+        
+        return None
+    
+    def _compare_versions(self, v1: VersionInfo, v2: VersionInfo) -> int:
+        """Compare two versions. Returns -1, 0, or 1."""
+        if (v1.major, v1.minor, v1.patch) < (v2.major, v2.minor, v2.patch):
+            return -1
+        elif (v1.major, v1.minor, v1.patch) > (v2.major, v2.minor, v2.patch):
+            return 1
+        else:
+            # Handle prerelease comparison
+            if v1.prerelease and not v2.prerelease:
+                return -1
+            elif not v1.prerelease and v2.prerelease:
+                return 1
+            elif v1.prerelease and v2.prerelease:
+                if v1.prerelease < v2.prerelease:
+                    return -1
+                elif v1.prerelease > v2.prerelease:
+                    return 1
+            
+            return 0
+    
+    def _get_latest_version(self, package_name: str, ecosystem: str) -> Optional[str]:
+        """Get latest version from package registry (simulated)."""
+        # Simulated latest versions for common packages
+        mock_versions = {
+            'lodash': '4.17.21',
+            'express': '4.18.2',
+            'react': '18.2.0',
+            'axios': '1.6.0',
+            'django': '4.2.11',
+            'requests': '2.31.0',
+            'numpy': '1.24.0',
+            'flask': '2.3.0',
+            'fastapi': '0.104.0',
+            'pytest': '7.4.0'
+        }
+        
+        # In production, would query actual package registries:
+        # npm: npm view <package> version
+        # pypi: pip index versions <package>
+        # maven: maven metadata API
+        
+        return mock_versions.get(package_name.lower())
+    
+    def _determine_update_type(self, current: VersionInfo, latest: VersionInfo) -> UpdateType:
+        """Determine the type of update based on semantic versioning."""
+        if latest.major > current.major:
+            return UpdateType.MAJOR
+        elif latest.minor > current.minor:
+            return UpdateType.MINOR
+        elif latest.patch > current.patch:
+            return UpdateType.PATCH
+        elif latest.prerelease and not current.prerelease:
+            return UpdateType.PRERELEASE
+        else:
+            return UpdateType.PATCH  # Default fallback
+    
+    def _assess_upgrade_risk(self, package_name: str, current: VersionInfo, latest: VersionInfo,
+                            ecosystem: str, update_type: UpdateType) -> UpgradeRisk:
+        """Assess the risk level of an upgrade."""
+        # Base risk assessment on update type
+        base_risk = {
+            UpdateType.PATCH: UpgradeRisk.SAFE,
+            UpdateType.MINOR: UpgradeRisk.LOW,
+            UpdateType.MAJOR: UpgradeRisk.HIGH,
+            UpdateType.PRERELEASE: UpgradeRisk.MEDIUM
+        }.get(update_type, UpgradeRisk.MEDIUM)
+        
+        # Adjust for package-specific factors
+        high_risk_packages = [
+            'webpack', 'babel', 'typescript', 'eslint',  # Build tools
+            'react', 'vue', 'angular',  # Frameworks
+            'django', 'flask', 'fastapi',  # Web frameworks
+            'spring-boot', 'hibernate'  # Java frameworks
+        ]
+        
+        if package_name.lower() in high_risk_packages and update_type == UpdateType.MAJOR:
+            base_risk = UpgradeRisk.CRITICAL
+        
+        # Check for known breaking changes
+        if self._has_known_breaking_changes(package_name, current, latest):
+            if base_risk in [UpgradeRisk.SAFE, UpgradeRisk.LOW]:
+                base_risk = UpgradeRisk.MEDIUM
+            elif base_risk == UpgradeRisk.MEDIUM:
+                base_risk = UpgradeRisk.HIGH
+        
+        return base_risk
+    
+    def _has_known_breaking_changes(self, package_name: str, current: VersionInfo, latest: VersionInfo) -> bool:
+        """Check if there are known breaking changes between versions."""
+        # Simulated breaking change detection
+        breaking_change_versions = {
+            'react': ['16.0.0', '17.0.0', '18.0.0'],
+            'django': ['2.0.0', '3.0.0', '4.0.0'],
+            'webpack': ['4.0.0', '5.0.0'],
+            'babel': ['7.0.0', '8.0.0'],
+            'typescript': ['4.0.0', '5.0.0']
+        }
+        
+        package_versions = breaking_change_versions.get(package_name.lower(), [])
+        latest_str = str(latest)
+        
+        return any(latest_str.startswith(v.split('.')[0]) for v in package_versions)
+    
+    def _check_security_updates(self, package_name: str, current_version: str, latest_version: str) -> List[str]:
+        """Check for security updates in the upgrade."""
+        security_updates = []
+        
+        if package_name in self.security_advisories:
+            for advisory in self.security_advisories[package_name]:
+                fixed_version = advisory['fixed_in']
+                
+                # Simple version comparison for security fixes
+                if (self._is_version_greater(fixed_version, current_version) and
+                    not self._is_version_greater(fixed_version, latest_version)):
+                    security_updates.append(f"{advisory['advisory_id']}: {advisory['description']}")
+        
+        return security_updates
+    
+    def _is_version_greater(self, v1: str, v2: str) -> bool:
+        """Simple version comparison."""
+        v1_parts = [int(x) for x in v1.split('.')]
+        v2_parts = [int(x) for x in v2.split('.')]
+        
+        # Pad shorter version
+        max_len = max(len(v1_parts), len(v2_parts))
+        v1_parts.extend([0] * (max_len - len(v1_parts)))
+        v2_parts.extend([0] * (max_len - len(v2_parts)))
+        
+        return v1_parts > v2_parts
+    
+    def _analyze_breaking_changes(self, package_name: str, current: VersionInfo, 
+                                 latest: VersionInfo, ecosystem: str) -> List[str]:
+        """Analyze potential breaking changes."""
+        breaking_changes = []
+        
+        # Check if major version change
+        if latest.major > current.major:
+            breaking_changes.append(f"Major version upgrade from {current.major}.x to {latest.major}.x")
+            
+            # Add ecosystem-specific common breaking changes
+            ecosystem_knowledge = self.ecosystem_knowledge.get(ecosystem, {})
+            common_changes = ecosystem_knowledge.get('common_breaking_changes', [])
+            breaking_changes.extend(common_changes[:2])  # Add top 2
+        
+        # Check for specific package patterns
+        if package_name.lower() == 'react' and latest.major >= 17:
+            breaking_changes.append("New JSX Transform")
+            if latest.major >= 18:
+                breaking_changes.append("Concurrent Rendering changes")
+        
+        elif package_name.lower() == 'django' and latest.major >= 4:
+            breaking_changes.append("CSRF token changes")
+            breaking_changes.append("Default AUTO_INCREMENT field changes")
+        
+        elif package_name.lower() == 'webpack' and latest.major >= 5:
+            breaking_changes.append("Module Federation support")
+            breaking_changes.append("Asset modules replace file-loader")
+        
+        return breaking_changes
+    
+    def _calculate_priority_score(self, update_type: UpdateType, risk_level: UpgradeRisk,
+                                 security_updates: List[str], is_direct: bool) -> float:
+        """Calculate priority score for upgrade (0-100)."""
+        score = 50.0  # Base score
+        
+        # Security updates get highest priority
+        if security_updates:
+            score += 30.0
+            score += len(security_updates) * 5.0  # Multiple security fixes
+        
+        # Update type scoring
+        type_scores = {
+            UpdateType.PATCH: 20.0,
+            UpdateType.MINOR: 10.0,
+            UpdateType.MAJOR: -10.0,
+            UpdateType.PRERELEASE: -5.0
+        }
+        score += type_scores.get(update_type, 0)
+        
+        # Risk level adjustment
+        risk_adjustments = {
+            UpgradeRisk.SAFE: 15.0,
+            UpgradeRisk.LOW: 5.0,
+            UpgradeRisk.MEDIUM: -5.0,
+            UpgradeRisk.HIGH: -15.0,
+            UpgradeRisk.CRITICAL: -25.0
+        }
+        score += risk_adjustments.get(risk_level, 0)
+        
+        # Direct dependencies get slightly higher priority
+        if is_direct:
+            score += 5.0
+        
+        return max(0.0, min(100.0, score))
+    
+    def _estimate_migration_effort(self, update_type: UpdateType, breaking_changes: List[str]) -> str:
+        """Estimate migration effort level."""
+        if update_type == UpdateType.PATCH and not breaking_changes:
+            return "Minimal"
+        elif update_type == UpdateType.MINOR and len(breaking_changes) <= 1:
+            return "Low"
+        elif update_type == UpdateType.MAJOR or len(breaking_changes) > 2:
+            return "High"
+        else:
+            return "Medium"
+    
+    def _get_affected_dependencies(self, package_name: str, dependency: Dict[str, Any]) -> List[str]:
+        """Get list of dependencies that might be affected by this upgrade."""
+        # Simulated dependency impact analysis
+        common_dependencies = {
+            'react': ['react-dom', 'react-router', 'react-redux'],
+            'django': ['djangorestframework', 'django-cors-headers', 'celery'],
+            'webpack': ['webpack-cli', 'webpack-dev-server', 'html-webpack-plugin'],
+            'babel': ['@babel/core', '@babel/preset-env', '@babel/preset-react']
+        }
+        
+        return common_dependencies.get(package_name.lower(), [])
+    
+    def _assess_rollback_complexity(self, update_type: UpdateType, risk_level: UpgradeRisk) -> str:
+        """Assess complexity of rolling back the upgrade."""
+        if update_type == UpdateType.PATCH:
+            return "Simple"
+        elif update_type == UpdateType.MINOR and risk_level in [UpgradeRisk.SAFE, UpgradeRisk.LOW]:
+            return "Simple"
+        elif risk_level in [UpgradeRisk.HIGH, UpgradeRisk.CRITICAL]:
+            return "Complex"
+        else:
+            return "Moderate"
+    
+    def _estimate_upgrade_time(self, update_type: UpdateType, breaking_changes: List[str]) -> str:
+        """Estimate time required for upgrade."""
+        base_times = {
+            UpdateType.PATCH: "30 minutes",
+            UpdateType.MINOR: "2 hours",
+            UpdateType.MAJOR: "1 day",
+            UpdateType.PRERELEASE: "4 hours"
+        }
+        
+        base_time = base_times.get(update_type, "4 hours")
+        
+        if len(breaking_changes) > 2:
+            if "30 minutes" in base_time:
+                base_time = "2 hours"
+            elif "2 hours" in base_time:
+                base_time = "1 day"
+            elif "1 day" in base_time:
+                base_time = "3 days"
+        
+        return base_time
+    
+    def _generate_upgrade_statistics(self, upgrades: List[DependencyUpgrade]) -> Dict[str, Any]:
+        """Generate statistics about available upgrades."""
+        if not upgrades:
+            return {}
+        
+        return {
+            'total_upgrades': len(upgrades),
+            'by_type': {
+                'patch': len([u for u in upgrades if u.update_type == UpdateType.PATCH]),
+                'minor': len([u for u in upgrades if u.update_type == UpdateType.MINOR]),
+                'major': len([u for u in upgrades if u.update_type == UpdateType.MAJOR]),
+                'prerelease': len([u for u in upgrades if u.update_type == UpdateType.PRERELEASE])
+            },
+            'by_risk': {
+                'safe': len([u for u in upgrades if u.risk_level == UpgradeRisk.SAFE]),
+                'low': len([u for u in upgrades if u.risk_level == UpgradeRisk.LOW]),
+                'medium': len([u for u in upgrades if u.risk_level == UpgradeRisk.MEDIUM]),
+                'high': len([u for u in upgrades if u.risk_level == UpgradeRisk.HIGH]),
+                'critical': len([u for u in upgrades if u.risk_level == UpgradeRisk.CRITICAL])
+            },
+            'security_updates': len([u for u in upgrades if u.security_updates]),
+            'direct_dependencies': len([u for u in upgrades if u.direct]),
+            'average_priority': sum(u.priority_score for u in upgrades) / len(upgrades)
+        }
+    
+    def _perform_risk_assessment(self, upgrades: List[DependencyUpgrade]) -> Dict[str, Any]:
+        """Perform comprehensive risk assessment."""
+        high_risk_upgrades = [u for u in upgrades if u.risk_level in [UpgradeRisk.HIGH, UpgradeRisk.CRITICAL]]
+        security_upgrades = [u for u in upgrades if u.security_updates]
+        major_upgrades = [u for u in upgrades if u.update_type == UpdateType.MAJOR]
+        
+        return {
+            'overall_risk': self._calculate_overall_upgrade_risk(upgrades),
+            'high_risk_count': len(high_risk_upgrades),
+            'security_critical_count': len(security_upgrades),
+            'major_version_count': len(major_upgrades),
+            'risk_factors': self._identify_risk_factors(upgrades),
+            'mitigation_strategies': self._suggest_mitigation_strategies(upgrades)
+        }
+    
+    def _calculate_overall_upgrade_risk(self, upgrades: List[DependencyUpgrade]) -> str:
+        """Calculate overall risk level for all upgrades."""
+        if not upgrades:
+            return "LOW"
+        
+        risk_scores = {
+            UpgradeRisk.SAFE: 1,
+            UpgradeRisk.LOW: 2,
+            UpgradeRisk.MEDIUM: 3,
+            UpgradeRisk.HIGH: 4,
+            UpgradeRisk.CRITICAL: 5
+        }
+        
+        total_score = sum(risk_scores.get(u.risk_level, 3) for u in upgrades)
+        average_score = total_score / len(upgrades)
+        
+        if average_score >= 4.0:
+            return "CRITICAL"
+        elif average_score >= 3.0:
+            return "HIGH"
+        elif average_score >= 2.0:
+            return "MEDIUM"
+        else:
+            return "LOW"
+    
+    def _identify_risk_factors(self, upgrades: List[DependencyUpgrade]) -> List[str]:
+        """Identify key risk factors across all upgrades."""
+        factors = []
+        
+        major_count = len([u for u in upgrades if u.update_type == UpdateType.MAJOR])
+        if major_count > 0:
+            factors.append(f"{major_count} major version upgrades with potential breaking changes")
+        
+        critical_count = len([u for u in upgrades if u.risk_level == UpgradeRisk.CRITICAL])
+        if critical_count > 0:
+            factors.append(f"{critical_count} critical risk upgrades requiring careful planning")
+        
+        framework_upgrades = [u for u in upgrades if any(fw in u.name.lower() 
+                             for fw in ['react', 'django', 'spring', 'webpack', 'babel'])]
+        if framework_upgrades:
+            factors.append(f"Core framework upgrades: {[u.name for u in framework_upgrades[:3]]}")
+        
+        return factors
+    
+    def _suggest_mitigation_strategies(self, upgrades: List[DependencyUpgrade]) -> List[str]:
+        """Suggest risk mitigation strategies."""
+        strategies = []
+        
+        high_risk_count = len([u for u in upgrades if u.risk_level in [UpgradeRisk.HIGH, UpgradeRisk.CRITICAL]])
+        if high_risk_count > 0:
+            strategies.append("Create comprehensive test suite before high-risk upgrades")
+            strategies.append("Plan rollback procedures for critical upgrades")
+        
+        major_count = len([u for u in upgrades if u.update_type == UpdateType.MAJOR])
+        if major_count > 3:
+            strategies.append("Phase major upgrades across multiple releases")
+            strategies.append("Use feature flags for gradual rollout")
+        
+        security_count = len([u for u in upgrades if u.security_updates])
+        if security_count > 0:
+            strategies.append("Prioritize security updates regardless of risk level")
+        
+        return strategies
+    
+    def _create_upgrade_plans(self, upgrades: List[DependencyUpgrade], timeline_days: int) -> List[UpgradePlan]:
+        """Create phased upgrade plans."""
+        if not upgrades:
+            return []
+        
+        # Sort upgrades by priority score (descending)
+        sorted_upgrades = sorted(upgrades, key=lambda x: x.priority_score, reverse=True)
+        
+        plans = []
+        
+        # Phase 1: Security and safe updates (first 30% of timeline)
+        phase1_upgrades = [u for u in sorted_upgrades if 
+                          u.security_updates or u.risk_level == UpgradeRisk.SAFE][:10]
+        if phase1_upgrades:
+            plans.append(self._create_upgrade_plan(
+                "Phase 1: Security & Safe Updates",
+                "Immediate security fixes and low-risk updates",
+                1, phase1_upgrades, timeline_days // 3
+            ))
+        
+        # Phase 2: Low-medium risk updates (middle 40% of timeline)
+        phase2_upgrades = [u for u in sorted_upgrades if 
+                          u.risk_level in [UpgradeRisk.LOW, UpgradeRisk.MEDIUM] and
+                          not u.security_updates][:8]
+        if phase2_upgrades:
+            plans.append(self._create_upgrade_plan(
+                "Phase 2: Regular Updates",
+                "Standard dependency updates with moderate risk",
+                2, phase2_upgrades, timeline_days * 2 // 5
+            ))
+        
+        # Phase 3: High-risk and major updates (final 30% of timeline)
+        phase3_upgrades = [u for u in sorted_upgrades if 
+                          u.risk_level in [UpgradeRisk.HIGH, UpgradeRisk.CRITICAL]][:5]
+        if phase3_upgrades:
+            plans.append(self._create_upgrade_plan(
+                "Phase 3: Major Updates",
+                "High-risk upgrades requiring careful planning",
+                3, phase3_upgrades, timeline_days // 3
+            ))
+        
+        return plans
+    
+    def _create_upgrade_plan(self, name: str, description: str, phase: int,
+                            upgrades: List[DependencyUpgrade], duration_days: int) -> UpgradePlan:
+        """Create a detailed upgrade plan for a phase."""
+        dependency_names = [u.name for u in upgrades]
+        
+        # Generate migration steps
+        migration_steps = []
+        migration_steps.append("1. Create feature branch for upgrades")
+        migration_steps.append("2. Update dependency versions in manifest files")
+        migration_steps.append("3. Run dependency install/update commands")
+        migration_steps.append("4. Fix breaking changes and deprecation warnings")
+        migration_steps.append("5. Update test suite for compatibility")
+        migration_steps.append("6. Run comprehensive test suite")
+        migration_steps.append("7. Update documentation and changelog")
+        migration_steps.append("8. Create pull request for review")
+        
+        # Add phase-specific steps
+        if phase == 1:
+            migration_steps.insert(3, "3a. Verify security fixes are applied")
+        elif phase == 3:
+            migration_steps.insert(5, "5a. Perform extensive integration testing")
+            migration_steps.insert(6, "6a. Test with production-like data")
+        
+        # Generate testing requirements
+        testing_requirements = [
+            "Unit test suite passes 100%",
+            "Integration tests cover upgrade scenarios",
+            "Performance benchmarks within acceptable range"
+        ]
+        
+        if any(u.risk_level in [UpgradeRisk.HIGH, UpgradeRisk.CRITICAL] for u in upgrades):
+            testing_requirements.extend([
+                "Manual testing of critical user flows",
+                "Load testing for performance regression",
+                "Security scanning for new vulnerabilities"
+            ])
+        
+        # Generate rollback plan
+        rollback_plan = [
+            "1. Revert dependency versions in manifest files",
+            "2. Run dependency install with previous versions",
+            "3. Restore previous configuration files if changed",
+            "4. Run smoke tests to verify rollback success",
+            "5. Monitor system health metrics"
+        ]
+        
+        # Success criteria
+        success_criteria = [
+            "All tests pass in CI/CD pipeline",
+            "No security vulnerabilities introduced",
+            "Performance metrics within acceptable thresholds",
+            "No critical user workflows broken"
+        ]
+        
+        return UpgradePlan(
+            name=name,
+            description=description,
+            phase=phase,
+            dependencies=dependency_names,
+            estimated_duration=f"{duration_days} days",
+            prerequisites=self._generate_prerequisites(upgrades),
+            migration_steps=migration_steps,
+            testing_requirements=testing_requirements,
+            rollback_plan=rollback_plan,
+            success_criteria=success_criteria
+        )
+    
+    def _generate_prerequisites(self, upgrades: List[DependencyUpgrade]) -> List[str]:
+        """Generate prerequisites for upgrade phase."""
+        prerequisites = [
+            "Comprehensive test suite with good coverage",
+            "Backup of current working state",
+            "Development environment setup"
+        ]
+        
+        if any(u.risk_level in [UpgradeRisk.HIGH, UpgradeRisk.CRITICAL] for u in upgrades):
+            prerequisites.extend([
+                "Staging environment for testing",
+                "Rollback procedure documented and tested",
+                "Team availability for issue resolution"
+            ])
+        
+        if any(u.security_updates for u in upgrades):
+            prerequisites.append("Security team notification for validation")
+        
+        return prerequisites
+    
+    def _generate_upgrade_recommendations(self, analysis_results: Dict[str, Any]) -> List[str]:
+        """Generate actionable upgrade recommendations."""
+        recommendations = []
+        
+        security_count = analysis_results['upgrade_statistics'].get('security_updates', 0)
+        if security_count > 0:
+            recommendations.append(f"URGENT: {security_count} security updates available - prioritize immediately")
+        
+        safe_count = analysis_results['upgrade_statistics']['by_risk'].get('safe', 0)
+        if safe_count > 0:
+            recommendations.append(f"Quick wins: {safe_count} safe updates can be applied with minimal risk")
+        
+        critical_count = analysis_results['risk_assessment']['high_risk_count']
+        if critical_count > 0:
+            recommendations.append(f"Plan carefully: {critical_count} high-risk upgrades need thorough testing")
+        
+        major_count = analysis_results['upgrade_statistics']['by_type'].get('major', 0)
+        if major_count > 3:
+            recommendations.append("Consider phasing major upgrades across multiple releases")
+        
+        overall_risk = analysis_results['risk_assessment']['overall_risk']
+        if overall_risk in ['HIGH', 'CRITICAL']:
+            recommendations.append("Overall upgrade risk is high - recommend gradual approach")
+        
+        return recommendations
+    
+    def generate_report(self, analysis_results: Dict[str, Any], format: str = 'text') -> str:
+        """Generate upgrade plan report in specified format."""
+        if format == 'json':
+            # Convert dataclass objects for JSON serialization
+            serializable_results = analysis_results.copy()
+            serializable_results['available_upgrades'] = [asdict(upgrade) for upgrade in analysis_results['available_upgrades']]
+            serializable_results['upgrade_plans'] = [asdict(plan) for plan in analysis_results['upgrade_plans']]
+            return json.dumps(serializable_results, indent=2, default=str)
+        
+        # Text format report
+        report = []
+        report.append("=" * 60)
+        report.append("DEPENDENCY UPGRADE PLAN")
+        report.append("=" * 60)
+        report.append(f"Generated: {analysis_results['timestamp']}")
+        report.append(f"Timeline: {analysis_results['timeline_days']} days")
+        report.append("")
+        
+        # Statistics
+        stats = analysis_results['upgrade_statistics']
+        report.append("UPGRADE SUMMARY:")
+        report.append(f"  Total Upgrades Available: {stats.get('total_upgrades', 0)}")
+        report.append(f"  Security Updates: {stats.get('security_updates', 0)}")
+        report.append(f"  Major Version Updates: {stats['by_type'].get('major', 0)}")
+        report.append(f"  High Risk Updates: {stats['by_risk'].get('high', 0)}")
+        report.append("")
+        
+        # Risk Assessment
+        risk = analysis_results['risk_assessment']
+        report.append("RISK ASSESSMENT:")
+        report.append(f"  Overall Risk Level: {risk['overall_risk']}")
+        if risk.get('risk_factors'):
+            report.append("  Key Risk Factors:")
+            for factor in risk['risk_factors'][:3]:
+                report.append(f"    • {factor}")
+        report.append("")
+        
+        # High Priority Upgrades
+        high_priority = sorted([u for u in analysis_results['available_upgrades']], 
+                              key=lambda x: x.priority_score, reverse=True)[:10]
+        
+        if high_priority:
+            report.append("TOP PRIORITY UPGRADES:")
+            report.append("-" * 30)
+            for upgrade in high_priority:
+                risk_indicator = "🔴" if upgrade.risk_level in [UpgradeRisk.HIGH, UpgradeRisk.CRITICAL] else \
+                               "🟡" if upgrade.risk_level == UpgradeRisk.MEDIUM else "🟢"
+                security_indicator = " 🔒" if upgrade.security_updates else ""
+                
+                report.append(f"{risk_indicator} {upgrade.name}: {upgrade.current_version} → {upgrade.latest_version}{security_indicator}")
+                report.append(f"   Type: {upgrade.update_type.value.title()} | Risk: {upgrade.risk_level.value.title()} | Priority: {upgrade.priority_score:.1f}")
+                if upgrade.security_updates:
+                    report.append(f"   Security: {upgrade.security_updates[0]}")
+                report.append("")
+        
+        # Upgrade Plans
+        if analysis_results['upgrade_plans']:
+            report.append("PHASED UPGRADE PLANS:")
+            report.append("-" * 30)
+            
+            for plan in analysis_results['upgrade_plans']:
+                report.append(f"{plan.name} ({plan.estimated_duration})")
+                report.append(f"  Dependencies: {', '.join(plan.dependencies[:5])}")
+                if len(plan.dependencies) > 5:
+                    report.append(f"  ... and {len(plan.dependencies) - 5} more")
+                report.append(f"  Key Steps: {'; '.join(plan.migration_steps[:3])}")
+                report.append("")
+        
+        # Recommendations
+        if analysis_results['recommendations']:
+            report.append("RECOMMENDATIONS:")
+            report.append("-" * 20)
+            for i, rec in enumerate(analysis_results['recommendations'], 1):
+                report.append(f"{i}. {rec}")
+            report.append("")
+        
+        report.append("=" * 60)
+        return '\n'.join(report)
+
+def main():
+    """Main entry point for the upgrade planner."""
+    parser = argparse.ArgumentParser(
+        description='Analyze dependency upgrades and create migration plans',
+        formatter_class=argparse.RawDescriptionHelpFormatter,
+        epilog="""
+Examples:
+  python upgrade_planner.py deps.json
+  python upgrade_planner.py inventory.json --timeline 60 --format json
+  python upgrade_planner.py deps.json --risk-threshold medium --output plan.txt
+        """
+    )
+    
+    parser.add_argument('inventory_file',
+                       help='Path to dependency inventory JSON file')
+    parser.add_argument('--timeline', type=int, default=90,
+                       help='Timeline for upgrade plan in days (default: 90)')
+    parser.add_argument('--format', choices=['text', 'json'], default='text',
+                       help='Output format (default: text)')
+    parser.add_argument('--output', '-o',
+                       help='Output file path (default: stdout)')
+    parser.add_argument('--risk-threshold', 
+                       choices=['safe', 'low', 'medium', 'high', 'critical'],
+                       default='high',
+                       help='Maximum risk level to include (default: high)')
+    parser.add_argument('--security-only', action='store_true',
+                       help='Only plan upgrades with security fixes')
+    
+    args = parser.parse_args()
+    
+    try:
+        planner = UpgradePlanner()
+        results = planner.analyze_upgrades(args.inventory_file, args.timeline)
+        
+        # Filter by risk threshold if specified
+        if args.risk_threshold != 'critical':
+            risk_levels = ['safe', 'low', 'medium', 'high', 'critical']
+            max_index = risk_levels.index(args.risk_threshold)
+            allowed_risks = set(risk_levels[:max_index + 1])
+            
+            results['available_upgrades'] = [
+                u for u in results['available_upgrades']
+                if u.risk_level.value in allowed_risks
+            ]
+        
+        # Filter for security-only if specified
+        if args.security_only:
+            results['available_upgrades'] = [
+                u for u in results['available_upgrades']
+                if u.security_updates
+            ]
+        
+        report = planner.generate_report(results, args.format)
+        
+        if args.output:
+            with open(args.output, 'w') as f:
+                f.write(report)
+            print(f"Upgrade plan saved to {args.output}")
+        else:
+            print(report)
+    
+    except Exception as e:
+        print(f"Error: {e}", file=sys.stderr)
+        sys.exit(1)
+
+if __name__ == '__main__':
+    main()