pomera-ai-commander 0.1.0 → 1.2.1

package/core/migration_manager.py

@@ -1,915 +1,915 @@
-"""
-Migration Manager for Settings Database Migration
-
-This module provides comprehensive migration capabilities between JSON settings files
-and the SQLite database format. It handles bidirectional conversion with full
-structure preservation, including complex nested structures, encrypted keys,
-and history arrays.
-
-Designed to handle all 15 tool configurations and complex data structures
-identified in the production codebase analysis.
-"""
-
-import json
-import sqlite3
-import os
-import shutil
-import logging
-from typing import Dict, List, Tuple, Any, Optional, Union
-from datetime import datetime
-from pathlib import Path
-
-from .database_connection_manager import DatabaseConnectionManager
-from .database_schema import DatabaseSchema, DataTypeConverter
-
-
-class MigrationManager:
-    """
-    Handles migration between JSON settings file and database format.
-    
-    Features:
-    - Bidirectional JSON ↔ Database conversion
-    - Full structure preservation for complex nested objects
-    - Special handling for encrypted API keys with "ENC:" prefix
-    - Support for all tool configurations and data types
-    - Migration validation and rollback capabilities
-    - Comprehensive error handling and recovery
-    """
-    
-    def __init__(self, connection_manager: DatabaseConnectionManager):
-        """
-        Initialize the migration manager.
-        
-        Args:
-            connection_manager: Database connection manager instance
-        """
-        self.connection_manager = connection_manager
-        self.logger = logging.getLogger(__name__)
-        self.schema = DatabaseSchema()
-        self.converter = DataTypeConverter()
-        
-        # Migration tracking
-        self._migration_history = []
-        self._max_history = 50
-        
-        # Validation settings
-        self._validation_enabled = True
-        self._strict_validation = True
-        
-        # Backup settings
-        self._auto_backup = True
-        self._backup_suffix = ".backup"
-        
-    def migrate_from_json(self, json_filepath: str, validate: bool = True) -> bool:
-        """
-        Convert settings.json to database format with full structure preservation.
-        
-        Args:
-            json_filepath: Path to source JSON settings file
-            validate: Whether to validate migration accuracy
-            
-        Returns:
-            True if migration successful, False otherwise
-        """
-        try:
-            self.logger.info(f"Starting migration from JSON: {json_filepath}")
-            
-            # Validate input file
-            if not os.path.exists(json_filepath):
-                self.logger.error(f"JSON file not found: {json_filepath}")
-                return False
-            
-            # Create backup if enabled
-            backup_path = None
-            if self._auto_backup:
-                backup_path = self.create_migration_backup(json_filepath)
-                if not backup_path:
-                    self.logger.warning("Failed to create backup, continuing without backup")
-            
-            # Load and parse JSON
-            json_data = self._load_json_file(json_filepath)
-            if json_data is None:
-                return False
-            
-            # Perform migration
-            success = self._migrate_json_to_database(json_data)
-            if not success:
-                self.logger.error("Migration to database failed")
-                return False
-            
-            # Validate migration if requested
-            if validate and self._validation_enabled:
-                validation_success = self._validate_json_migration(json_data)
-                if not validation_success:
-                    self.logger.error("Migration validation failed")
-                    if self._strict_validation:
-                        return False
-            
-            # Record successful migration
-            self._record_migration_success(json_filepath, backup_path, "json_to_db")
-            
-            self.logger.info("JSON to database migration completed successfully")
-            return True
-            
-        except Exception as e:
-            self.logger.error(f"Migration from JSON failed: {e}")
-            self._record_migration_failure(json_filepath, str(e), "json_to_db")
-            return False
-    
-    def migrate_to_json(self, json_filepath: str, validate: bool = True) -> bool:
-        """
-        Convert database back to settings.json format.
-        
-        Args:
-            json_filepath: Target path for JSON settings file
-            validate: Whether to validate migration accuracy
-            
-        Returns:
-            True if migration successful, False otherwise
-        """
-        try:
-            self.logger.info(f"Starting migration to JSON: {json_filepath}")
-            
-            # Create backup of existing file if it exists
-            backup_path = None
-            if os.path.exists(json_filepath) and self._auto_backup:
-                backup_path = self.create_migration_backup(json_filepath)
-            
-            # Extract data from database
-            json_data = self._migrate_database_to_json()
-            if json_data is None:
-                return False
-            
-            # Write JSON file
-            success = self._write_json_file(json_filepath, json_data)
-            if not success:
-                return False
-            
-            # Validate migration if requested
-            if validate and self._validation_enabled:
-                validation_success = self._validate_db_migration(json_data)
-                if not validation_success:
-                    self.logger.error("Migration validation failed")
-                    if self._strict_validation:
-                        return False
-            
-            # Record successful migration
-            self._record_migration_success(json_filepath, backup_path, "db_to_json")
-            
-            self.logger.info("Database to JSON migration completed successfully")
-            return True
-            
-        except Exception as e:
-            self.logger.error(f"Migration to JSON failed: {e}")
-            self._record_migration_failure(json_filepath, str(e), "db_to_json")
-            return False
-    
-    def validate_migration(self, original_json: Dict, migrated_json: Dict) -> bool:
-        """
-        Verify migration accuracy by comparing original and migrated data.
-        
-        Args:
-            original_json: Original JSON data structure
-            migrated_json: Migrated JSON data structure
-            
-        Returns:
-            True if migration is accurate, False otherwise
-        """
-        try:
-            self.logger.info("Starting migration validation")
-            
-            # Deep comparison of data structures
-            validation_results = self._deep_compare_structures(original_json, migrated_json)
-            
-            if validation_results['success']:
-                self.logger.info("Migration validation passed")
-                return True
-            else:
-                self.logger.error(f"Migration validation failed: {validation_results['errors']}")
-                return False
-                
-        except Exception as e:
-            self.logger.error(f"Migration validation error: {e}")
-            return False
-    
-    def create_migration_backup(self, json_filepath: str) -> Optional[str]:
-        """
-        Create backup of original JSON file before migration.
-        
-        Args:
-            json_filepath: Path to JSON file to backup
-            
-        Returns:
-            Path to backup file if successful, None otherwise
-        """
-        try:
-            timestamp = datetime.now().strftime("%Y%m%d_%H%M%S")
-            backup_path = f"{json_filepath}{self._backup_suffix}_{timestamp}"
-            
-            shutil.copy2(json_filepath, backup_path)
-            
-            self.logger.info(f"Created migration backup: {backup_path}")
-            return backup_path
-            
-        except Exception as e:
-            self.logger.error(f"Failed to create backup: {e}")
-            return None
-    
-    def rollback_migration(self, backup_filepath: str) -> bool:
-        """
-        Rollback to original JSON file if migration fails.
-        
-        Args:
-            backup_filepath: Path to backup file to restore
-            
-        Returns:
-            True if rollback successful, False otherwise
-        """
-        try:
-            if not os.path.exists(backup_filepath):
-                self.logger.error(f"Backup file not found: {backup_filepath}")
-                return False
-            
-            # Determine original file path by removing backup suffix
-            original_path = backup_filepath
-            for suffix in [self._backup_suffix]:
-                if suffix in original_path:
-                    original_path = original_path.split(suffix)[0]
-                    break
-            
-            # Restore original file
-            shutil.copy2(backup_filepath, original_path)
-            
-            self.logger.info(f"Rollback completed: restored {original_path}")
-            return True
-            
-        except Exception as e:
-            self.logger.error(f"Rollback failed: {e}")
-            return False
-    
-    def get_migration_history(self) -> List[Dict[str, Any]]:
-        """
-        Get history of migration operations.
-        
-        Returns:
-            List of migration history entries
-        """
-        return self._migration_history.copy()
-    
-    def clear_migration_history(self) -> None:
-        """Clear migration history."""
-        self._migration_history.clear()
-        self.logger.info("Migration history cleared")
-    
-    # Private implementation methods
-    
-    def _load_json_file(self, filepath: str) -> Optional[Dict[str, Any]]:
-        """
-        Load and parse JSON settings file with error handling.
-        
-        Args:
-            filepath: Path to JSON file
-            
-        Returns:
-            Parsed JSON data or None if failed
-        """
-        try:
-            with open(filepath, 'r', encoding='utf-8') as f:
-                data = json.load(f)
-            
-            self.logger.debug(f"Loaded JSON file: {filepath}")
-            return data
-            
-        except json.JSONDecodeError as e:
-            self.logger.error(f"Invalid JSON in file {filepath}: {e}")
-            return None
-        except Exception as e:
-            self.logger.error(f"Failed to load JSON file {filepath}: {e}")
-            return None
-    
-    def _write_json_file(self, filepath: str, data: Dict[str, Any]) -> bool:
-        """
-        Write JSON data to file with proper formatting.
-        
-        Args:
-            filepath: Target file path
-            data: JSON data to write
-            
-        Returns:
-            True if successful, False otherwise
-        """
-        try:
-            # Ensure directory exists
-            os.makedirs(os.path.dirname(filepath), exist_ok=True)
-            
-            with open(filepath, 'w', encoding='utf-8') as f:
-                json.dump(data, f, indent=2, ensure_ascii=False)
-            
-            self.logger.debug(f"Wrote JSON file: {filepath}")
-            return True
-            
-        except Exception as e:
-            self.logger.error(f"Failed to write JSON file {filepath}: {e}")
-            return False
-    
-    def _migrate_json_to_database(self, json_data: Dict[str, Any]) -> bool:
-        """
-        Migrate JSON data structure to database tables.
-        
-        Args:
-            json_data: Parsed JSON settings data
-            
-        Returns:
-            True if migration successful, False otherwise
-        """
-        try:
-            with self.connection_manager.transaction() as conn:
-                # Clear existing data
-                self._clear_all_tables(conn)
-                
-                # Migrate core settings
-                self._migrate_core_settings(conn, json_data)
-                
-                # Migrate tool settings
-                if 'tool_settings' in json_data:
-                    self._migrate_tool_settings(conn, json_data['tool_settings'])
-                
-                # Migrate tab content
-                self._migrate_tab_content(conn, json_data)
-                
-                # Migrate performance settings
-                if 'performance_settings' in json_data:
-                    self._migrate_performance_settings(conn, json_data['performance_settings'])
-                
-                # Migrate font settings
-                if 'font_settings' in json_data:
-                    self._migrate_font_settings(conn, json_data['font_settings'])
-                
-                # Migrate dialog settings
-                if 'dialog_settings' in json_data:
-                    self._migrate_dialog_settings(conn, json_data['dialog_settings'])
-                
-                # Update metadata
-                self._update_migration_metadata(conn)
-            
-            self.logger.info("JSON to database migration completed")
-            return True
-            
-        except Exception as e:
-            self.logger.error(f"JSON to database migration failed: {e}")
-            return False
-    
-    def _migrate_database_to_json(self) -> Optional[Dict[str, Any]]:
-        """
-        Extract data from database and reconstruct JSON structure.
-        
-        Returns:
-            Reconstructed JSON data or None if failed
-        """
-        try:
-            conn = self.connection_manager.get_connection()
-            
-            json_data = {}
-            
-            # Extract core settings
-            core_settings = self._extract_core_settings(conn)
-            json_data.update(core_settings)
-            
-            # Extract tool settings
-            tool_settings = self._extract_tool_settings(conn)
-            json_data['tool_settings'] = tool_settings  # Always include, even if empty
-            
-            # Extract tab content
-            tab_content = self._extract_tab_content(conn)
-            json_data.update(tab_content)
-            
-            # Extract performance settings
-            performance_settings = self._extract_performance_settings(conn)
-            json_data['performance_settings'] = performance_settings  # Always include, even if empty
-            
-            # Extract font settings
-            font_settings = self._extract_font_settings(conn)
-            json_data['font_settings'] = font_settings  # Always include, even if empty
-            
-            # Extract dialog settings
-            dialog_settings = self._extract_dialog_settings(conn)
-            json_data['dialog_settings'] = dialog_settings  # Always include, even if empty
-            
-            self.logger.info("Database to JSON extraction completed")
-            return json_data
-            
-        except Exception as e:
-            self.logger.error(f"Database to JSON extraction failed: {e}")
-            return None
-    
-    def _clear_all_tables(self, conn: sqlite3.Connection) -> None:
-        """Clear all data from settings tables."""
-        tables = [
-            'core_settings', 'tool_settings', 'tab_content',
-            'performance_settings', 'font_settings', 'dialog_settings'
-        ]
-        
-        for table in tables:
-            conn.execute(f"DELETE FROM {table}")
-    
-    def _migrate_core_settings(self, conn: sqlite3.Connection, json_data: Dict[str, Any]) -> None:
-        """
-        Migrate core application settings to database.
-        
-        Args:
-            conn: Database connection
-            json_data: Full JSON data structure
-        """
-        # Core settings are top-level keys excluding special categories
-        excluded_keys = {
-            'tool_settings', 'input_tabs', 'output_tabs', 
-            'performance_settings', 'font_settings', 'dialog_settings'
-        }
-        
-        for key, value in json_data.items():
-            if key not in excluded_keys:
-                data_type = self.converter.python_to_db_type(value)
-                serialized_value = self.converter.serialize_value(value)
-                
-                conn.execute(
-                    "INSERT INTO core_settings (key, value, data_type) VALUES (?, ?, ?)",
-                    (key, serialized_value, data_type)
-                )
-    
-    def _migrate_tool_settings(self, conn: sqlite3.Connection, tool_settings: Dict[str, Any]) -> None:
-        """
-        Migrate tool-specific settings to database with nested path support.
-        
-        Args:
-            conn: Database connection
-            tool_settings: Tool settings dictionary
-        """
-        for tool_name, tool_config in tool_settings.items():
-            if isinstance(tool_config, dict):
-                # Flatten nested tool configuration
-                flattened = self._flatten_nested_dict(tool_config)
-                
-                for setting_path, value in flattened.items():
-                    data_type = self.converter.python_to_db_type(value)
-                    serialized_value = self.converter.serialize_value(value)
-                    
-                    conn.execute(
-                        "INSERT INTO tool_settings (tool_name, setting_path, setting_value, data_type) VALUES (?, ?, ?, ?)",
-                        (tool_name, setting_path, serialized_value, data_type)
-                    )
-            else:
-                # Simple tool setting
-                data_type = self.converter.python_to_db_type(tool_config)
-                serialized_value = self.converter.serialize_value(tool_config)
-                
-                conn.execute(
-                    "INSERT INTO tool_settings (tool_name, setting_path, setting_value, data_type) VALUES (?, ?, ?, ?)",
-                    (tool_name, 'value', serialized_value, data_type)
-                )
-    
-    def _migrate_tab_content(self, conn: sqlite3.Connection, json_data: Dict[str, Any]) -> None:
-        """
-        Migrate input_tabs and output_tabs arrays to database.
-        
-        Args:
-            conn: Database connection
-            json_data: Full JSON data structure
-        """
-        # Migrate input tabs
-        if 'input_tabs' in json_data:
-            input_tabs = json_data['input_tabs']
-            for i, content in enumerate(input_tabs):
-                conn.execute(
-                    "INSERT INTO tab_content (tab_type, tab_index, content) VALUES (?, ?, ?)",
-                    ('input', i, content or '')
-                )
-        
-        # Migrate output tabs
-        if 'output_tabs' in json_data:
-            output_tabs = json_data['output_tabs']
-            for i, content in enumerate(output_tabs):
-                conn.execute(
-                    "INSERT INTO tab_content (tab_type, tab_index, content) VALUES (?, ?, ?)",
-                    ('output', i, content or '')
-                )
-    
-    def _migrate_performance_settings(self, conn: sqlite3.Connection, performance_settings: Dict[str, Any]) -> None:
-        """
-        Migrate performance settings with nested structure support.
-        
-        Args:
-            conn: Database connection
-            performance_settings: Performance settings dictionary
-        """
-        for category, settings in performance_settings.items():
-            if isinstance(settings, dict):
-                # Nested performance category
-                flattened = self._flatten_nested_dict(settings)
-                
-                for setting_key, value in flattened.items():
-                    data_type = self.converter.python_to_db_type(value)
-                    serialized_value = self.converter.serialize_value(value)
-                    
-                    conn.execute(
-                        "INSERT INTO performance_settings (category, setting_key, setting_value, data_type) VALUES (?, ?, ?, ?)",
-                        (category, setting_key, serialized_value, data_type)
-                    )
-            else:
-                # Simple performance setting
-                data_type = self.converter.python_to_db_type(settings)
-                serialized_value = self.converter.serialize_value(settings)
-                
-                conn.execute(
-                    "INSERT INTO performance_settings (category, setting_key, setting_value, data_type) VALUES (?, ?, ?, ?)",
-                    (category, 'value', serialized_value, data_type)
-                )
-    
-    def _migrate_font_settings(self, conn: sqlite3.Connection, font_settings: Dict[str, Any]) -> None:
-        """
-        Migrate font settings with platform-specific fallbacks.
-        
-        Args:
-            conn: Database connection
-            font_settings: Font settings dictionary
-        """
-        for font_type, font_config in font_settings.items():
-            if isinstance(font_config, dict):
-                for property_name, value in font_config.items():
-                    data_type = self.converter.python_to_db_type(value)
-                    serialized_value = self.converter.serialize_value(value)
-                    
-                    conn.execute(
-                        "INSERT INTO font_settings (font_type, property, value, data_type) VALUES (?, ?, ?, ?)",
-                        (font_type, property_name, serialized_value, data_type)
-                    )
-    
-    def _migrate_dialog_settings(self, conn: sqlite3.Connection, dialog_settings: Dict[str, Any]) -> None:
-        """
-        Migrate dialog settings with category-based organization.
-        
-        Args:
-            conn: Database connection
-            dialog_settings: Dialog settings dictionary
-        """
-        for category, dialog_config in dialog_settings.items():
-            if isinstance(dialog_config, dict):
-                for property_name, value in dialog_config.items():
-                    data_type = self.converter.python_to_db_type(value)
-                    serialized_value = self.converter.serialize_value(value)
-                    
-                    self.logger.debug(f"Inserting dialog setting: {category}.{property_name} = {value} (type: {data_type})")
-                    
-                    conn.execute(
-                        "INSERT INTO dialog_settings (category, property, value, data_type) VALUES (?, ?, ?, ?)",
-                        (category, property_name, serialized_value, data_type)
-                    )
-    
-    def _update_migration_metadata(self, conn: sqlite3.Connection) -> None:
-        """Update migration metadata in database."""
-        timestamp = datetime.now().isoformat()
-        
-        # Update or insert migration metadata
-        metadata_updates = [
-            ('last_migration_date', timestamp),
-            ('migration_type', 'json_to_db'),
-            ('migration_status', 'completed')
-        ]
-        
-        for key, value in metadata_updates:
-            conn.execute(
-                "INSERT OR REPLACE INTO settings_metadata (key, value) VALUES (?, ?)",
-                (key, value)
-            )
-    
-    def _extract_core_settings(self, conn: sqlite3.Connection) -> Dict[str, Any]:
-        """
-        Extract core settings from database and convert to appropriate types.
-        
-        Args:
-            conn: Database connection
-            
-        Returns:
-            Dictionary of core settings
-        """
-        core_settings = {}
-        
-        cursor = conn.execute("SELECT key, value, data_type FROM core_settings")
-        for key, value, data_type in cursor.fetchall():
-            core_settings[key] = self.converter.deserialize_value(value, data_type)
-        
-        return core_settings
-    
-    def _extract_tool_settings(self, conn: sqlite3.Connection) -> Dict[str, Any]:
-        """
-        Extract tool settings from database and reconstruct nested structure.
-        
-        Args:
-            conn: Database connection
-            
-        Returns:
-            Dictionary of tool settings with nested structure
-        """
-        tool_settings = {}
-        
-        cursor = conn.execute(
-            "SELECT tool_name, setting_path, setting_value, data_type FROM tool_settings ORDER BY tool_name, setting_path"
-        )
-        
-        for tool_name, setting_path, setting_value, data_type in cursor.fetchall():
-            if tool_name not in tool_settings:
-                tool_settings[tool_name] = {}
-            
-            # Deserialize value
-            value = self.converter.deserialize_value(setting_value, data_type)
-            
-            # Handle nested paths
-            if '.' in setting_path:
-                self._set_nested_value(tool_settings[tool_name], setting_path, value)
-            else:
-                tool_settings[tool_name][setting_path] = value
-        
-        # Post-process: unwrap simple tool settings that only have a 'value' key
-        for tool_name, tool_config in list(tool_settings.items()):
-            if isinstance(tool_config, dict) and len(tool_config) == 1 and 'value' in tool_config:
-                tool_settings[tool_name] = tool_config['value']
-        
-        return tool_settings
-    
-    def _extract_tab_content(self, conn: sqlite3.Connection) -> Dict[str, List[str]]:
-        """
-        Extract tab content from database and reconstruct arrays.
-        
-        Args:
-            conn: Database connection
-            
-        Returns:
-            Dictionary with input_tabs and output_tabs arrays
-        """
-        tab_content = {'input_tabs': [''] * 7, 'output_tabs': [''] * 7}
-        
-        cursor = conn.execute("SELECT tab_type, tab_index, content FROM tab_content ORDER BY tab_type, tab_index")
-        
-        for tab_type, tab_index, content in cursor.fetchall():
-            if tab_type == 'input' and 0 <= tab_index < 7:
-                tab_content['input_tabs'][tab_index] = content or ''
-            elif tab_type == 'output' and 0 <= tab_index < 7:
-                tab_content['output_tabs'][tab_index] = content or ''
-        
-        return tab_content
-    
-    def _extract_performance_settings(self, conn: sqlite3.Connection) -> Dict[str, Any]:
-        """
-        Extract performance settings from database and reconstruct nested structure.
-        
-        Args:
-            conn: Database connection
-            
-        Returns:
-            Dictionary of performance settings with nested structure
-        """
-        performance_settings = {}
-        
-        cursor = conn.execute(
-            "SELECT category, setting_key, setting_value, data_type FROM performance_settings ORDER BY category, setting_key"
-        )
-        
-        for category, setting_key, setting_value, data_type in cursor.fetchall():
-            if category not in performance_settings:
-                performance_settings[category] = {}
-            
-            # Deserialize value
-            value = self.converter.deserialize_value(setting_value, data_type)
-            
-            # Handle nested paths
-            if '.' in setting_key:
-                self._set_nested_value(performance_settings[category], setting_key, value)
-            else:
-                performance_settings[category][setting_key] = value
-        
-        # Post-process: unwrap simple categories that only have a 'value' key
-        for category, category_config in list(performance_settings.items()):
-            if isinstance(category_config, dict) and len(category_config) == 1 and 'value' in category_config:
-                performance_settings[category] = category_config['value']
-        
-        return performance_settings
-    
-    def _extract_font_settings(self, conn: sqlite3.Connection) -> Dict[str, Any]:
-        """
-        Extract font settings from database.
-        
-        Args:
-            conn: Database connection
-            
-        Returns:
-            Dictionary of font settings
-        """
-        font_settings = {}
-        
-        cursor = conn.execute("SELECT font_type, property, value, data_type FROM font_settings ORDER BY font_type, property")
-        
-        for font_type, property_name, value, data_type in cursor.fetchall():
-            if font_type not in font_settings:
-                font_settings[font_type] = {}
-            
-            font_settings[font_type][property_name] = self.converter.deserialize_value(value, data_type)
-        
-        return font_settings
-    
-    def _extract_dialog_settings(self, conn: sqlite3.Connection) -> Dict[str, Any]:
-        """
-        Extract dialog settings from database.
-        
-        Args:
-            conn: Database connection
-            
-        Returns:
-            Dictionary of dialog settings
-        """
-        dialog_settings = {}
-        
-        cursor = conn.execute("SELECT category, property, value, data_type FROM dialog_settings ORDER BY category, property")
-        
-        for category, property_name, value, data_type in cursor.fetchall():
-            if category not in dialog_settings:
-                dialog_settings[category] = {}
-            
-            dialog_settings[category][property_name] = self.converter.deserialize_value(value, data_type)
-        
-        return dialog_settings
-    
-    def _flatten_nested_dict(self, nested_dict: Dict[str, Any], parent_key: str = '', separator: str = '.') -> Dict[str, Any]:
-        """
-        Flatten nested dictionary using dot notation for keys.
-        
-        Args:
-            nested_dict: Dictionary to flatten
-            parent_key: Parent key prefix
-            separator: Key separator character
-            
-        Returns:
-            Flattened dictionary with dot-notation keys
-        """
-        items = []
-        
-        for key, value in nested_dict.items():
-            new_key = f"{parent_key}{separator}{key}" if parent_key else key
-            
-            if isinstance(value, dict) and len(value) > 0:
-                # Only recursively flatten non-empty dictionaries
-                items.extend(self._flatten_nested_dict(value, new_key, separator).items())
-            else:
-                # Treat empty dictionaries and all other values as leaf nodes
-                items.append((new_key, value))
-        
-        return dict(items)
-    
-    def _set_nested_value(self, target_dict: Dict[str, Any], key_path: str, value: Any, separator: str = '.') -> None:
-        """
-        Set value in nested dictionary using dot notation key path.
-        
-        Args:
-            target_dict: Dictionary to modify
-            key_path: Dot-notation key path
-            value: Value to set
-            separator: Key separator character
-        """
-        keys = key_path.split(separator)
-        current = target_dict
-        
-        # Navigate to parent of target key
-        for key in keys[:-1]:
-            if key not in current:
-                current[key] = {}
-            current = current[key]
-        
-        # Set final value
-        current[keys[-1]] = value
-    
-    def _validate_json_migration(self, original_json: Dict[str, Any]) -> bool:
-        """
-        Validate JSON to database migration by comparing original with reconstructed data.
-        
-        Args:
-            original_json: Original JSON data
-            
-        Returns:
-            True if validation passes, False otherwise
-        """
-        try:
-            # Reconstruct JSON from database
-            reconstructed_json = self._migrate_database_to_json()
-            
-            if reconstructed_json is None:
-                return False
-            
-            # Compare structures
-            comparison_result = self._deep_compare_structures(original_json, reconstructed_json)
-            
-            if not comparison_result['success']:
-                self.logger.error(f"Validation errors: {comparison_result['errors'][:5]}")  # Show first 5 errors
-            
-            return comparison_result['success']
-            
-        except Exception as e:
-            self.logger.error(f"JSON migration validation failed: {e}")
-            return False
-    
-    def _validate_db_migration(self, expected_json: Dict[str, Any]) -> bool:
-        """
-        Validate database to JSON migration by comparing with expected data.
-        
-        Args:
-            expected_json: Expected JSON structure
-            
-        Returns:
-            True if validation passes, False otherwise
-        """
-        try:
-            # This would be called after database to JSON migration
-            # The expected_json is what we expect to get from the database
-            return True  # Simplified for now
-            
-        except Exception as e:
-            self.logger.error(f"Database migration validation failed: {e}")
-            return False
-    
-    def _deep_compare_structures(self, dict1: Dict[str, Any], dict2: Dict[str, Any]) -> Dict[str, Any]:
-        """
-        Perform deep comparison of two dictionary structures.
-        
-        Args:
-            dict1: First dictionary
-            dict2: Second dictionary
-            
-        Returns:
-            Dictionary with comparison results and any errors found
-        """
-        errors = []
-        
-        # Check keys in dict1
-        for key in dict1:
-            if key not in dict2:
-                errors.append(f"Key '{key}' missing in second dictionary")
-            else:
-                # Compare values
-                val1, val2 = dict1[key], dict2[key]
-                
-                if isinstance(val1, dict) and isinstance(val2, dict):
-                    # Recursive comparison for nested dictionaries
-                    nested_result = self._deep_compare_structures(val1, val2)
-                    if not nested_result['success']:
-                        errors.extend([f"{key}.{error}" for error in nested_result['errors']])
-                elif isinstance(val1, list) and isinstance(val2, list):
-                    # Compare lists
-                    if len(val1) != len(val2):
-                        errors.append(f"List '{key}' length mismatch: {len(val1)} vs {len(val2)}")
-                    else:
-                        for i, (item1, item2) in enumerate(zip(val1, val2)):
-                            if item1 != item2:
-                                errors.append(f"List '{key}[{i}]' value mismatch: {item1} vs {item2}")
-                elif val1 != val2:
-                    errors.append(f"Value '{key}' mismatch: {val1} vs {val2}")
-        
-        # Check for extra keys in dict2
-        for key in dict2:
-            if key not in dict1:
-                errors.append(f"Extra key '{key}' in second dictionary")
-        
-        return {
-            'success': len(errors) == 0,
-            'errors': errors
-        }
-    
-    def _record_migration_success(self, filepath: str, backup_path: Optional[str], migration_type: str) -> None:
-        """Record successful migration in history."""
-        entry = {
-            'timestamp': datetime.now().isoformat(),
-            'type': migration_type,
-            'filepath': filepath,
-            'backup_path': backup_path,
-            'status': 'success',
-            'error': None
-        }
-        
-        self._migration_history.append(entry)
-        
-        # Keep only recent history
-        if len(self._migration_history) > self._max_history:
-            self._migration_history = self._migration_history[-self._max_history:]
-    
-    def _record_migration_failure(self, filepath: str, error: str, migration_type: str) -> None:
-        """Record failed migration in history."""
-        entry = {
-            'timestamp': datetime.now().isoformat(),
-            'type': migration_type,
-            'filepath': filepath,
-            'backup_path': None,
-            'status': 'failure',
-            'error': error
-        }
-        
-        self._migration_history.append(entry)
-        
-        # Keep only recent history
-        if len(self._migration_history) > self._max_history:
+"""
+Migration Manager for Settings Database Migration
+
+This module provides comprehensive migration capabilities between JSON settings files
+and the SQLite database format. It handles bidirectional conversion with full
+structure preservation, including complex nested structures, encrypted keys,
+and history arrays.
+
+Designed to handle all 15 tool configurations and complex data structures
+identified in the production codebase analysis.
+"""
+
+import json
+import sqlite3
+import os
+import shutil
+import logging
+from typing import Dict, List, Tuple, Any, Optional, Union
+from datetime import datetime
+from pathlib import Path
+
+from .database_connection_manager import DatabaseConnectionManager
+from .database_schema import DatabaseSchema, DataTypeConverter
+
+
+class MigrationManager:
+    """
+    Handles migration between JSON settings file and database format.
+    
+    Features:
+    - Bidirectional JSON ↔ Database conversion
+    - Full structure preservation for complex nested objects
+    - Special handling for encrypted API keys with "ENC:" prefix
+    - Support for all tool configurations and data types
+    - Migration validation and rollback capabilities
+    - Comprehensive error handling and recovery
+    """
+    
+    def __init__(self, connection_manager: DatabaseConnectionManager):
+        """
+        Initialize the migration manager.
+        
+        Args:
+            connection_manager: Database connection manager instance
+        """
+        self.connection_manager = connection_manager
+        self.logger = logging.getLogger(__name__)
+        self.schema = DatabaseSchema()
+        self.converter = DataTypeConverter()
+        
+        # Migration tracking
+        self._migration_history = []
+        self._max_history = 50
+        
+        # Validation settings
+        self._validation_enabled = True
+        self._strict_validation = True
+        
+        # Backup settings
+        self._auto_backup = True
+        self._backup_suffix = ".backup"
+        
+    def migrate_from_json(self, json_filepath: str, validate: bool = True) -> bool:
+        """
+        Convert settings.json to database format with full structure preservation.
+        
+        Args:
+            json_filepath: Path to source JSON settings file
+            validate: Whether to validate migration accuracy
+            
+        Returns:
+            True if migration successful, False otherwise
+        """
+        try:
+            self.logger.info(f"Starting migration from JSON: {json_filepath}")
+            
+            # Validate input file
+            if not os.path.exists(json_filepath):
+                self.logger.error(f"JSON file not found: {json_filepath}")
+                return False
+            
+            # Create backup if enabled
+            backup_path = None
+            if self._auto_backup:
+                backup_path = self.create_migration_backup(json_filepath)
+                if not backup_path:
+                    self.logger.warning("Failed to create backup, continuing without backup")
+            
+            # Load and parse JSON
+            json_data = self._load_json_file(json_filepath)
+            if json_data is None:
+                return False
+            
+            # Perform migration
+            success = self._migrate_json_to_database(json_data)
+            if not success:
+                self.logger.error("Migration to database failed")
+                return False
+            
+            # Validate migration if requested
+            if validate and self._validation_enabled:
+                validation_success = self._validate_json_migration(json_data)
+                if not validation_success:
+                    self.logger.error("Migration validation failed")
+                    if self._strict_validation:
+                        return False
+            
+            # Record successful migration
+            self._record_migration_success(json_filepath, backup_path, "json_to_db")
+            
+            self.logger.info("JSON to database migration completed successfully")
+            return True
+            
+        except Exception as e:
+            self.logger.error(f"Migration from JSON failed: {e}")
+            self._record_migration_failure(json_filepath, str(e), "json_to_db")
+            return False
+    
+    def migrate_to_json(self, json_filepath: str, validate: bool = True) -> bool:
+        """
+        Convert database back to settings.json format.
+        
+        Args:
+            json_filepath: Target path for JSON settings file
+            validate: Whether to validate migration accuracy
+            
+        Returns:
+            True if migration successful, False otherwise
+        """
+        try:
+            self.logger.info(f"Starting migration to JSON: {json_filepath}")
+            
+            # Create backup of existing file if it exists
+            backup_path = None
+            if os.path.exists(json_filepath) and self._auto_backup:
+                backup_path = self.create_migration_backup(json_filepath)
+            
+            # Extract data from database
+            json_data = self._migrate_database_to_json()
+            if json_data is None:
+                return False
+            
+            # Write JSON file
+            success = self._write_json_file(json_filepath, json_data)
+            if not success:
+                return False
+            
+            # Validate migration if requested
+            if validate and self._validation_enabled:
+                validation_success = self._validate_db_migration(json_data)
+                if not validation_success:
+                    self.logger.error("Migration validation failed")
+                    if self._strict_validation:
+                        return False
+            
+            # Record successful migration
+            self._record_migration_success(json_filepath, backup_path, "db_to_json")
+            
+            self.logger.info("Database to JSON migration completed successfully")
+            return True
+            
+        except Exception as e:
+            self.logger.error(f"Migration to JSON failed: {e}")
+            self._record_migration_failure(json_filepath, str(e), "db_to_json")
+            return False
+    
+    def validate_migration(self, original_json: Dict, migrated_json: Dict) -> bool:
+        """
+        Verify migration accuracy by comparing original and migrated data.
+        
+        Args:
+            original_json: Original JSON data structure
+            migrated_json: Migrated JSON data structure
+            
+        Returns:
+            True if migration is accurate, False otherwise
+        """
+        try:
+            self.logger.info("Starting migration validation")
+            
+            # Deep comparison of data structures
+            validation_results = self._deep_compare_structures(original_json, migrated_json)
+            
+            if validation_results['success']:
+                self.logger.info("Migration validation passed")
+                return True
+            else:
+                self.logger.error(f"Migration validation failed: {validation_results['errors']}")
+                return False
+                
+        except Exception as e:
+            self.logger.error(f"Migration validation error: {e}")
+            return False
+    
+    def create_migration_backup(self, json_filepath: str) -> Optional[str]:
+        """
+        Create backup of original JSON file before migration.
+        
+        Args:
+            json_filepath: Path to JSON file to backup
+            
+        Returns:
+            Path to backup file if successful, None otherwise
+        """
+        try:
+            timestamp = datetime.now().strftime("%Y%m%d_%H%M%S")
+            backup_path = f"{json_filepath}{self._backup_suffix}_{timestamp}"
+            
+            shutil.copy2(json_filepath, backup_path)
+            
+            self.logger.info(f"Created migration backup: {backup_path}")
+            return backup_path
+            
+        except Exception as e:
+            self.logger.error(f"Failed to create backup: {e}")
+            return None
+    
+    def rollback_migration(self, backup_filepath: str) -> bool:
+        """
+        Rollback to original JSON file if migration fails.
+        
+        Args:
+            backup_filepath: Path to backup file to restore
+            
+        Returns:
+            True if rollback successful, False otherwise
+        """
+        try:
+            if not os.path.exists(backup_filepath):
+                self.logger.error(f"Backup file not found: {backup_filepath}")
+                return False
+            
+            # Determine original file path by removing backup suffix
+            original_path = backup_filepath
+            for suffix in [self._backup_suffix]:
+                if suffix in original_path:
+                    original_path = original_path.split(suffix)[0]
+                    break
+            
+            # Restore original file
+            shutil.copy2(backup_filepath, original_path)
+            
+            self.logger.info(f"Rollback completed: restored {original_path}")
+            return True
+            
+        except Exception as e:
+            self.logger.error(f"Rollback failed: {e}")
+            return False
+    
+    def get_migration_history(self) -> List[Dict[str, Any]]:
+        """
+        Get history of migration operations.
+        
+        Returns:
+            List of migration history entries
+        """
+        return self._migration_history.copy()
+    
+    def clear_migration_history(self) -> None:
+        """Clear migration history."""
+        self._migration_history.clear()
+        self.logger.info("Migration history cleared")
+    
+    # Private implementation methods
+    
+    def _load_json_file(self, filepath: str) -> Optional[Dict[str, Any]]:
+        """
+        Load and parse JSON settings file with error handling.
+        
+        Args:
+            filepath: Path to JSON file
+            
+        Returns:
+            Parsed JSON data or None if failed
+        """
+        try:
+            with open(filepath, 'r', encoding='utf-8') as f:
+                data = json.load(f)
+            
+            self.logger.debug(f"Loaded JSON file: {filepath}")
+            return data
+            
+        except json.JSONDecodeError as e:
+            self.logger.error(f"Invalid JSON in file {filepath}: {e}")
+            return None
+        except Exception as e:
+            self.logger.error(f"Failed to load JSON file {filepath}: {e}")
+            return None
+    
+    def _write_json_file(self, filepath: str, data: Dict[str, Any]) -> bool:
+        """
+        Write JSON data to file with proper formatting.
+        
+        Args:
+            filepath: Target file path
+            data: JSON data to write
+            
+        Returns:
+            True if successful, False otherwise
+        """
+        try:
+            # Ensure directory exists
+            os.makedirs(os.path.dirname(filepath), exist_ok=True)
+            
+            with open(filepath, 'w', encoding='utf-8') as f:
+                json.dump(data, f, indent=2, ensure_ascii=False)
+            
+            self.logger.debug(f"Wrote JSON file: {filepath}")
+            return True
+            
+        except Exception as e:
+            self.logger.error(f"Failed to write JSON file {filepath}: {e}")
+            return False
+    
+    def _migrate_json_to_database(self, json_data: Dict[str, Any]) -> bool:
+        """
+        Migrate JSON data structure to database tables.
+        
+        Args:
+            json_data: Parsed JSON settings data
+            
+        Returns:
+            True if migration successful, False otherwise
+        """
+        try:
+            with self.connection_manager.transaction() as conn:
+                # Clear existing data
+                self._clear_all_tables(conn)
+                
+                # Migrate core settings
+                self._migrate_core_settings(conn, json_data)
+                
+                # Migrate tool settings
+                if 'tool_settings' in json_data:
+                    self._migrate_tool_settings(conn, json_data['tool_settings'])
+                
+                # Migrate tab content
+                self._migrate_tab_content(conn, json_data)
+                
+                # Migrate performance settings
+                if 'performance_settings' in json_data:
+                    self._migrate_performance_settings(conn, json_data['performance_settings'])
+                
+                # Migrate font settings
+                if 'font_settings' in json_data:
+                    self._migrate_font_settings(conn, json_data['font_settings'])
+                
+                # Migrate dialog settings
+                if 'dialog_settings' in json_data:
+                    self._migrate_dialog_settings(conn, json_data['dialog_settings'])
+                
+                # Update metadata
+                self._update_migration_metadata(conn)
+            
+            self.logger.info("JSON to database migration completed")
+            return True
+            
+        except Exception as e:
+            self.logger.error(f"JSON to database migration failed: {e}")
+            return False
+    
+    def _migrate_database_to_json(self) -> Optional[Dict[str, Any]]:
+        """
+        Extract data from database and reconstruct JSON structure.
+        
+        Returns:
+            Reconstructed JSON data or None if failed
+        """
+        try:
+            conn = self.connection_manager.get_connection()
+            
+            json_data = {}
+            
+            # Extract core settings
+            core_settings = self._extract_core_settings(conn)
+            json_data.update(core_settings)
+            
+            # Extract tool settings
+            tool_settings = self._extract_tool_settings(conn)
+            json_data['tool_settings'] = tool_settings  # Always include, even if empty
+            
+            # Extract tab content
+            tab_content = self._extract_tab_content(conn)
+            json_data.update(tab_content)
+            
+            # Extract performance settings
+            performance_settings = self._extract_performance_settings(conn)
+            json_data['performance_settings'] = performance_settings  # Always include, even if empty
+            
+            # Extract font settings
+            font_settings = self._extract_font_settings(conn)
+            json_data['font_settings'] = font_settings  # Always include, even if empty
+            
+            # Extract dialog settings
+            dialog_settings = self._extract_dialog_settings(conn)
+            json_data['dialog_settings'] = dialog_settings  # Always include, even if empty
+            
+            self.logger.info("Database to JSON extraction completed")
+            return json_data
+            
+        except Exception as e:
+            self.logger.error(f"Database to JSON extraction failed: {e}")
+            return None
+    
+    def _clear_all_tables(self, conn: sqlite3.Connection) -> None:
+        """Clear all data from settings tables."""
+        tables = [
+            'core_settings', 'tool_settings', 'tab_content',
+            'performance_settings', 'font_settings', 'dialog_settings'
+        ]
+        
+        for table in tables:
+            conn.execute(f"DELETE FROM {table}")
+    
+    def _migrate_core_settings(self, conn: sqlite3.Connection, json_data: Dict[str, Any]) -> None:
+        """
+        Migrate core application settings to database.
+        
+        Args:
+            conn: Database connection
+            json_data: Full JSON data structure
+        """
+        # Core settings are top-level keys excluding special categories
+        excluded_keys = {
+            'tool_settings', 'input_tabs', 'output_tabs', 
+            'performance_settings', 'font_settings', 'dialog_settings'
+        }
+        
+        for key, value in json_data.items():
+            if key not in excluded_keys:
+                data_type = self.converter.python_to_db_type(value)
+                serialized_value = self.converter.serialize_value(value)
+                
+                conn.execute(
+                    "INSERT INTO core_settings (key, value, data_type) VALUES (?, ?, ?)",
+                    (key, serialized_value, data_type)
+                )
+    
+    def _migrate_tool_settings(self, conn: sqlite3.Connection, tool_settings: Dict[str, Any]) -> None:
+        """
+        Migrate tool-specific settings to database with nested path support.
+        
+        Args:
+            conn: Database connection
+            tool_settings: Tool settings dictionary
+        """
+        for tool_name, tool_config in tool_settings.items():
+            if isinstance(tool_config, dict):
+                # Flatten nested tool configuration
+                flattened = self._flatten_nested_dict(tool_config)
+                
+                for setting_path, value in flattened.items():
+                    data_type = self.converter.python_to_db_type(value)
+                    serialized_value = self.converter.serialize_value(value)
+                    
+                    conn.execute(
+                        "INSERT INTO tool_settings (tool_name, setting_path, setting_value, data_type) VALUES (?, ?, ?, ?)",
+                        (tool_name, setting_path, serialized_value, data_type)
+                    )
+            else:
+                # Simple tool setting
+                data_type = self.converter.python_to_db_type(tool_config)
+                serialized_value = self.converter.serialize_value(tool_config)
+                
+                conn.execute(
+                    "INSERT INTO tool_settings (tool_name, setting_path, setting_value, data_type) VALUES (?, ?, ?, ?)",
+                    (tool_name, 'value', serialized_value, data_type)
+                )
+    
+    def _migrate_tab_content(self, conn: sqlite3.Connection, json_data: Dict[str, Any]) -> None:
+        """
+        Migrate input_tabs and output_tabs arrays to database.
+        
+        Args:
+            conn: Database connection
+            json_data: Full JSON data structure
+        """
+        # Migrate input tabs
+        if 'input_tabs' in json_data:
+            input_tabs = json_data['input_tabs']
+            for i, content in enumerate(input_tabs):
+                conn.execute(
+                    "INSERT INTO tab_content (tab_type, tab_index, content) VALUES (?, ?, ?)",
+                    ('input', i, content or '')
+                )
+        
+        # Migrate output tabs
+        if 'output_tabs' in json_data:
+            output_tabs = json_data['output_tabs']
+            for i, content in enumerate(output_tabs):
+                conn.execute(
+                    "INSERT INTO tab_content (tab_type, tab_index, content) VALUES (?, ?, ?)",
+                    ('output', i, content or '')
+                )
+    
+    def _migrate_performance_settings(self, conn: sqlite3.Connection, performance_settings: Dict[str, Any]) -> None:
+        """
+        Migrate performance settings with nested structure support.
+        
+        Args:
+            conn: Database connection
+            performance_settings: Performance settings dictionary
+        """
+        for category, settings in performance_settings.items():
+            if isinstance(settings, dict):
+                # Nested performance category
+                flattened = self._flatten_nested_dict(settings)
+                
+                for setting_key, value in flattened.items():
+                    data_type = self.converter.python_to_db_type(value)
+                    serialized_value = self.converter.serialize_value(value)
+                    
+                    conn.execute(
+                        "INSERT INTO performance_settings (category, setting_key, setting_value, data_type) VALUES (?, ?, ?, ?)",
+                        (category, setting_key, serialized_value, data_type)
+                    )
+            else:
+                # Simple performance setting
+                data_type = self.converter.python_to_db_type(settings)
+                serialized_value = self.converter.serialize_value(settings)
+                
+                conn.execute(
+                    "INSERT INTO performance_settings (category, setting_key, setting_value, data_type) VALUES (?, ?, ?, ?)",
+                    (category, 'value', serialized_value, data_type)
+                )
+    
+    def _migrate_font_settings(self, conn: sqlite3.Connection, font_settings: Dict[str, Any]) -> None:
+        """
+        Migrate font settings with platform-specific fallbacks.
+        
+        Args:
+            conn: Database connection
+            font_settings: Font settings dictionary
+        """
+        for font_type, font_config in font_settings.items():
+            if isinstance(font_config, dict):
+                for property_name, value in font_config.items():
+                    data_type = self.converter.python_to_db_type(value)
+                    serialized_value = self.converter.serialize_value(value)
+                    
+                    conn.execute(
+                        "INSERT INTO font_settings (font_type, property, value, data_type) VALUES (?, ?, ?, ?)",
+                        (font_type, property_name, serialized_value, data_type)
+                    )
+    
+    def _migrate_dialog_settings(self, conn: sqlite3.Connection, dialog_settings: Dict[str, Any]) -> None:
+        """
+        Migrate dialog settings with category-based organization.
+        
+        Args:
+            conn: Database connection
+            dialog_settings: Dialog settings dictionary
+        """
+        for category, dialog_config in dialog_settings.items():
+            if isinstance(dialog_config, dict):
+                for property_name, value in dialog_config.items():
+                    data_type = self.converter.python_to_db_type(value)
+                    serialized_value = self.converter.serialize_value(value)
+                    
+                    self.logger.debug(f"Inserting dialog setting: {category}.{property_name} = {value} (type: {data_type})")
+                    
+                    conn.execute(
+                        "INSERT INTO dialog_settings (category, property, value, data_type) VALUES (?, ?, ?, ?)",
+                        (category, property_name, serialized_value, data_type)
+                    )
+    
+    def _update_migration_metadata(self, conn: sqlite3.Connection) -> None:
+        """Update migration metadata in database."""
+        timestamp = datetime.now().isoformat()
+        
+        # Update or insert migration metadata
+        metadata_updates = [
+            ('last_migration_date', timestamp),
+            ('migration_type', 'json_to_db'),
+            ('migration_status', 'completed')
+        ]
+        
+        for key, value in metadata_updates:
+            conn.execute(
+                "INSERT OR REPLACE INTO settings_metadata (key, value) VALUES (?, ?)",
+                (key, value)
+            )
+    
+    def _extract_core_settings(self, conn: sqlite3.Connection) -> Dict[str, Any]:
+        """
+        Extract core settings from database and convert to appropriate types.
+        
+        Args:
+            conn: Database connection
+            
+        Returns:
+            Dictionary of core settings
+        """
+        core_settings = {}
+        
+        cursor = conn.execute("SELECT key, value, data_type FROM core_settings")
+        for key, value, data_type in cursor.fetchall():
+            core_settings[key] = self.converter.deserialize_value(value, data_type)
+        
+        return core_settings
+    
+    def _extract_tool_settings(self, conn: sqlite3.Connection) -> Dict[str, Any]:
+        """
+        Extract tool settings from database and reconstruct nested structure.
+        
+        Args:
+            conn: Database connection
+            
+        Returns:
+            Dictionary of tool settings with nested structure
+        """
+        tool_settings = {}
+        
+        cursor = conn.execute(
+            "SELECT tool_name, setting_path, setting_value, data_type FROM tool_settings ORDER BY tool_name, setting_path"
+        )
+        
+        for tool_name, setting_path, setting_value, data_type in cursor.fetchall():
+            if tool_name not in tool_settings:
+                tool_settings[tool_name] = {}
+            
+            # Deserialize value
+            value = self.converter.deserialize_value(setting_value, data_type)
+            
+            # Handle nested paths
+            if '.' in setting_path:
+                self._set_nested_value(tool_settings[tool_name], setting_path, value)
+            else:
+                tool_settings[tool_name][setting_path] = value
+        
+        # Post-process: unwrap simple tool settings that only have a 'value' key
+        for tool_name, tool_config in list(tool_settings.items()):
+            if isinstance(tool_config, dict) and len(tool_config) == 1 and 'value' in tool_config:
+                tool_settings[tool_name] = tool_config['value']
+        
+        return tool_settings
+    
+    def _extract_tab_content(self, conn: sqlite3.Connection) -> Dict[str, List[str]]:
+        """
+        Extract tab content from database and reconstruct arrays.
+        
+        Args:
+            conn: Database connection
+            
+        Returns:
+            Dictionary with input_tabs and output_tabs arrays
+        """
+        tab_content = {'input_tabs': [''] * 7, 'output_tabs': [''] * 7}
+        
+        cursor = conn.execute("SELECT tab_type, tab_index, content FROM tab_content ORDER BY tab_type, tab_index")
+        
+        for tab_type, tab_index, content in cursor.fetchall():
+            if tab_type == 'input' and 0 <= tab_index < 7:
+                tab_content['input_tabs'][tab_index] = content or ''
+            elif tab_type == 'output' and 0 <= tab_index < 7:
+                tab_content['output_tabs'][tab_index] = content or ''
+        
+        return tab_content
+    
+    def _extract_performance_settings(self, conn: sqlite3.Connection) -> Dict[str, Any]:
+        """
+        Extract performance settings from database and reconstruct nested structure.
+        
+        Args:
+            conn: Database connection
+            
+        Returns:
+            Dictionary of performance settings with nested structure
+        """
+        performance_settings = {}
+        
+        cursor = conn.execute(
+            "SELECT category, setting_key, setting_value, data_type FROM performance_settings ORDER BY category, setting_key"
+        )
+        
+        for category, setting_key, setting_value, data_type in cursor.fetchall():
+            if category not in performance_settings:
+                performance_settings[category] = {}
+            
+            # Deserialize value
+            value = self.converter.deserialize_value(setting_value, data_type)
+            
+            # Handle nested paths
+            if '.' in setting_key:
+                self._set_nested_value(performance_settings[category], setting_key, value)
+            else:
+                performance_settings[category][setting_key] = value
+        
+        # Post-process: unwrap simple categories that only have a 'value' key
+        for category, category_config in list(performance_settings.items()):
+            if isinstance(category_config, dict) and len(category_config) == 1 and 'value' in category_config:
+                performance_settings[category] = category_config['value']
+        
+        return performance_settings
+    
+    def _extract_font_settings(self, conn: sqlite3.Connection) -> Dict[str, Any]:
+        """
+        Extract font settings from database.
+        
+        Args:
+            conn: Database connection
+            
+        Returns:
+            Dictionary of font settings
+        """
+        font_settings = {}
+        
+        cursor = conn.execute("SELECT font_type, property, value, data_type FROM font_settings ORDER BY font_type, property")
+        
+        for font_type, property_name, value, data_type in cursor.fetchall():
+            if font_type not in font_settings:
+                font_settings[font_type] = {}
+            
+            font_settings[font_type][property_name] = self.converter.deserialize_value(value, data_type)
+        
+        return font_settings
+    
+    def _extract_dialog_settings(self, conn: sqlite3.Connection) -> Dict[str, Any]:
+        """
+        Extract dialog settings from database.
+        
+        Args:
+            conn: Database connection
+            
+        Returns:
+            Dictionary of dialog settings
+        """
+        dialog_settings = {}
+        
+        cursor = conn.execute("SELECT category, property, value, data_type FROM dialog_settings ORDER BY category, property")
+        
+        for category, property_name, value, data_type in cursor.fetchall():
+            if category not in dialog_settings:
+                dialog_settings[category] = {}
+            
+            dialog_settings[category][property_name] = self.converter.deserialize_value(value, data_type)
+        
+        return dialog_settings
+    
+    def _flatten_nested_dict(self, nested_dict: Dict[str, Any], parent_key: str = '', separator: str = '.') -> Dict[str, Any]:
+        """
+        Flatten nested dictionary using dot notation for keys.
+        
+        Args:
+            nested_dict: Dictionary to flatten
+            parent_key: Parent key prefix
+            separator: Key separator character
+            
+        Returns:
+            Flattened dictionary with dot-notation keys
+        """
+        items = []
+        
+        for key, value in nested_dict.items():
+            new_key = f"{parent_key}{separator}{key}" if parent_key else key
+            
+            if isinstance(value, dict) and len(value) > 0:
+                # Only recursively flatten non-empty dictionaries
+                items.extend(self._flatten_nested_dict(value, new_key, separator).items())
+            else:
+                # Treat empty dictionaries and all other values as leaf nodes
+                items.append((new_key, value))
+        
+        return dict(items)
+    
+    def _set_nested_value(self, target_dict: Dict[str, Any], key_path: str, value: Any, separator: str = '.') -> None:
+        """
+        Set value in nested dictionary using dot notation key path.
+        
+        Args:
+            target_dict: Dictionary to modify
+            key_path: Dot-notation key path
+            value: Value to set
+            separator: Key separator character
+        """
+        keys = key_path.split(separator)
+        current = target_dict
+        
+        # Navigate to parent of target key
+        for key in keys[:-1]:
+            if key not in current:
+                current[key] = {}
+            current = current[key]
+        
+        # Set final value
+        current[keys[-1]] = value
+    
+    def _validate_json_migration(self, original_json: Dict[str, Any]) -> bool:
+        """
+        Validate JSON to database migration by comparing original with reconstructed data.
+        
+        Args:
+            original_json: Original JSON data
+            
+        Returns:
+            True if validation passes, False otherwise
+        """
+        try:
+            # Reconstruct JSON from database
+            reconstructed_json = self._migrate_database_to_json()
+            
+            if reconstructed_json is None:
+                return False
+            
+            # Compare structures
+            comparison_result = self._deep_compare_structures(original_json, reconstructed_json)
+            
+            if not comparison_result['success']:
+                self.logger.error(f"Validation errors: {comparison_result['errors'][:5]}")  # Show first 5 errors
+            
+            return comparison_result['success']
+            
+        except Exception as e:
+            self.logger.error(f"JSON migration validation failed: {e}")
+            return False
+    
+    def _validate_db_migration(self, expected_json: Dict[str, Any]) -> bool:
+        """
+        Validate database to JSON migration by comparing with expected data.
+        
+        Args:
+            expected_json: Expected JSON structure
+            
+        Returns:
+            True if validation passes, False otherwise
+        """
+        try:
+            # This would be called after database to JSON migration
+            # The expected_json is what we expect to get from the database
+            return True  # Simplified for now
+            
+        except Exception as e:
+            self.logger.error(f"Database migration validation failed: {e}")
+            return False
+    
+    def _deep_compare_structures(self, dict1: Dict[str, Any], dict2: Dict[str, Any]) -> Dict[str, Any]:
+        """
+        Perform deep comparison of two dictionary structures.
+        
+        Args:
+            dict1: First dictionary
+            dict2: Second dictionary
+            
+        Returns:
+            Dictionary with comparison results and any errors found
+        """
+        errors = []
+        
+        # Check keys in dict1
+        for key in dict1:
+            if key not in dict2:
+                errors.append(f"Key '{key}' missing in second dictionary")
+            else:
+                # Compare values
+                val1, val2 = dict1[key], dict2[key]
+                
+                if isinstance(val1, dict) and isinstance(val2, dict):
+                    # Recursive comparison for nested dictionaries
+                    nested_result = self._deep_compare_structures(val1, val2)
+                    if not nested_result['success']:
+                        errors.extend([f"{key}.{error}" for error in nested_result['errors']])
+                elif isinstance(val1, list) and isinstance(val2, list):
+                    # Compare lists
+                    if len(val1) != len(val2):
+                        errors.append(f"List '{key}' length mismatch: {len(val1)} vs {len(val2)}")
+                    else:
+                        for i, (item1, item2) in enumerate(zip(val1, val2)):
+                            if item1 != item2:
+                                errors.append(f"List '{key}[{i}]' value mismatch: {item1} vs {item2}")
+                elif val1 != val2:
+                    errors.append(f"Value '{key}' mismatch: {val1} vs {val2}")
+        
+        # Check for extra keys in dict2
+        for key in dict2:
+            if key not in dict1:
+                errors.append(f"Extra key '{key}' in second dictionary")
+        
+        return {
+            'success': len(errors) == 0,
+            'errors': errors
+        }
+    
+    def _record_migration_success(self, filepath: str, backup_path: Optional[str], migration_type: str) -> None:
+        """Record successful migration in history."""
+        entry = {
+            'timestamp': datetime.now().isoformat(),
+            'type': migration_type,
+            'filepath': filepath,
+            'backup_path': backup_path,
+            'status': 'success',
+            'error': None
+        }
+        
+        self._migration_history.append(entry)
+        
+        # Keep only recent history
+        if len(self._migration_history) > self._max_history:
+            self._migration_history = self._migration_history[-self._max_history:]
+    
+    def _record_migration_failure(self, filepath: str, error: str, migration_type: str) -> None:
+        """Record failed migration in history."""
+        entry = {
+            'timestamp': datetime.now().isoformat(),
+            'type': migration_type,
+            'filepath': filepath,
+            'backup_path': None,
+            'status': 'failure',
+            'error': error
+        }
+        
+        self._migration_history.append(entry)
+        
+        # Keep only recent history
+        if len(self._migration_history) > self._max_history:
             self._migration_history = self._migration_history[-self._max_history:]