diff --git a/CLAUDE.md b/CLAUDE.md
index 5c5d1e66..54fe7f6d 100644
--- a/CLAUDE.md
+++ b/CLAUDE.md
@@ -66,10 +66,199 @@ The application will use a central `config.json` file to store:
 - **COMPLETED**: Clean, functional button design with immediate accessibility
 
 **Active Work**:
-- ⏳ Additional UI polish and user experience improvements
-- ⏳ Matching engine development for cross-service track matching
+- 🎯 **PRIORITY FEATURE**: Spotify Matched Download System - Advanced music organization with intelligent matching
+- ⏳ Additional UI polish and user experience improvements  
+- ⏳ Enhanced matching engine development for cross-service track matching
 
-**Current System Status**: All major download management functionality is working correctly.
+**Current System Status**: All major download management functionality is working correctly. Ready for advanced Spotify integration features.
+
+---
+
+# 🎯 MAJOR FEATURE: Spotify Matched Download & Organization System
+
+## 🎯 Feature Overview
+
+**Ultimate Goal**: Transform downloaded music files into a perfectly organized library with Spotify-accurate metadata and professional folder structure.
+
+**Core Concept**: Add "Matched Download" buttons (🎯) alongside regular download buttons that automatically:
+1. Download the track using existing Soulseek integration
+2. Intelligently match the track with Spotify's database for accurate metadata
+3. Transfer and organize the file into a professional folder structure
+4. Handle complex edge cases like remixes, compilations, and mixed-artist albums
+
+**Target Folder Structure**:
+```
+Transfer/
+├── Taylor Swift/
+│   ├── Taylor Swift - 1989 (Taylor's Version)/
+│   │   ├── Taylor Swift - Shake It Off (Taylor's Version).flac
+│   │   ├── Taylor Swift - Blank Space (Taylor's Version).flac
+│   │   └── ...
+│   └── Taylor Swift - Folklore/
+│       ├── Taylor Swift - Cardigan.flac
+│       └── ...
+├── Daft Punk/
+│   └── Daft Punk - Random Access Memories/
+│       ├── Daft Punk - Get Lucky (feat. Pharrell Williams).flac
+│       └── ...
+└── Various Artists/
+    └── Various Artists - Now That's What I Call Music 50/
+        ├── Britney Spears - Toxic.flac
+        └── ...
+```
+
+## 🚀 Implementation Phases
+
+### Phase 1: Foundation & Architecture ⏳
+**Status**: In Planning
+**Deliverables**:
+- ✅ Comprehensive specification document (SPOTIFY_MATCHING_SPEC.md)
+- ⏳ Advanced metadata extraction system leveraging existing TrackResult/AlbumResult data
+- ⏳ Sophisticated matching algorithms with multi-stage fallback logic
+- ⏳ Professional UI architecture with responsive modal design
+
+### Phase 2: Core Services Development 📋
+**Status**: Pending Phase 1
+**Deliverables**:
+- SpotifyMatchingService with intelligent search query generation
+- FileOrganizationService with atomic file operations and conflict resolution
+- MatchingEngine with confidence scoring and remix detection
+- Enhanced error handling and logging systems
+
+### Phase 3: Professional UI Implementation 🎨
+**Status**: Pending Phase 2  
+**Deliverables**:
+- Responsive MatchingModal with proper spacing and layouts
+- Real-time search interface with debouncing and progress indicators
+- Confidence visualization and user feedback systems
+- Accessibility features and keyboard navigation
+
+### Phase 4: Integration & Polish ⚡
+**Status**: Pending Phase 3
+**Deliverables**:
+- 🎯 Matched download buttons integrated into existing UI components
+- Download completion detection and automatic processing
+- Album-level matching and batch processing capabilities
+- Comprehensive testing and edge case handling
+
+## 🎵 Supported Download Types
+
+### 1. **Singles** (Primary Focus)
+- Individual tracks from search results
+- Most straightforward matching scenario
+- Foundation for more complex matching logic
+
+### 2. **Albums** (Future Enhancement)
+- Complete album downloads with track-by-track matching
+- Handle mixed-artist compilations intelligently
+- Detect and separate "fake albums" (user playlists disguised as albums)
+
+### 3. **Individual Album Tracks** (Future Enhancement)
+- Tracks downloaded individually from within album results
+- Inherit album context for better matching accuracy
+- Maintain consistency with full album downloads
+
+## 🧠 Intelligent Matching System
+
+### Advanced Metadata Extraction
+**Challenge**: Soulseek filenames are inconsistent and unreliable
+**Solution**: Multi-source metadata aggregation
+- **Primary**: Leverage existing `TrackResult.artist`, `TrackResult.title`, `TrackResult.album` fields
+- **Secondary**: Enhanced filename parsing with regex patterns
+- **Tertiary**: Directory path analysis for album context
+- **Fallback**: Manual user input through search interface
+
+### Sophisticated Search Strategies
+1. **Exact Match**: Artist + Title + Album (highest confidence)
+2. **Partial Match**: Artist + Title (good confidence) 
+3. **Fuzzy Match**: Normalized strings with similarity scoring
+4. **Remix Detection**: Extract remix artist from title patterns
+5. **Manual Search**: User-driven fallback with suggestions
+
+### Confidence Scoring System
+- **90-100%**: Exact metadata match, auto-proceed
+- **75-89%**: High confidence, show for user confirmation
+- **60-74%**: Medium confidence, require user review
+- **Below 60%**: Low confidence, manual search required
+
+## 🎛️ User Experience Flow
+
+### Seamless Workflow
+1. **User clicks 🎯** on any track (single or within album)
+2. **Download starts immediately** using existing proven download system
+3. **Matching modal appears** with elegant, responsive design
+4. **Automatic matching runs** in background with progress indication
+5. **Results displayed** with confidence scores and preview information
+6. **User confirms or refines** the match through intuitive interface
+7. **File transferred atomically** to organized structure
+8. **Success feedback** with option to open destination folder
+
+### Error Handling & Fallbacks
+- **No automatic match**: Manual search interface with intelligent suggestions
+- **Multiple high-confidence matches**: User selection with detailed comparison
+- **No suitable matches found**: Option to proceed with regular download
+- **File transfer errors**: Rollback mechanisms and detailed error reporting
+- **Spotify API failures**: Graceful degradation with retry logic
+
+## 🔧 Technical Challenges & Solutions
+
+### Challenge 1: Inconsistent Soulseek Metadata
+**Problem**: Filenames like "Track 01.mp3" or "asdjkfh - some song.flac"
+**Solution**: Multi-stage extraction using existing TrackResult fields + enhanced parsing
+
+### Challenge 2: Remix Track Attribution  
+**Problem**: "Song Title (Artist Remix)" should match to remix artist, not original
+**Solution**: Regex-based remix detection with artist extraction patterns
+
+### Challenge 3: Album vs Playlist Distinction
+**Problem**: User playlists disguised as "albums" with mixed artists
+**Solution**: Artist consistency analysis and intelligent categorization
+
+### Challenge 4: File Organization Conflicts
+**Problem**: Duplicate files, naming conflicts, atomic operations
+**Solution**: Professional file management with backup, rollback, and deduplication
+
+### Challenge 5: Spotify API Rate Limits
+**Problem**: Search throttling and request failures
+**Solution**: Intelligent caching, request batching, and exponential backoff
+
+## ⚙️ Configuration & Settings
+
+### User Preferences
+- **Auto-match threshold**: Minimum confidence for automatic processing
+- **Folder naming patterns**: Customizable organization schemes  
+- **Transfer location**: Default destination directory
+- **Conflict resolution**: Overwrite, rename, or skip duplicate files
+- **Remix handling**: Original artist vs remix artist preference
+
+### Advanced Options
+- **Search aggressiveness**: Number of search strategies to attempt
+- **Metadata sources**: Priority order for information extraction
+- **Quality preferences**: File format and bitrate handling
+- **Cover art download**: Album artwork integration
+
+## 🎯 Success Criteria
+
+### Functional Requirements
+- [ ] 95%+ success rate for popular tracks with clear metadata
+- [ ] Graceful fallback handling for edge cases
+- [ ] Sub-3-second matching time for typical searches
+- [ ] Professional folder organization matching industry standards
+- [ ] Zero data loss during file operations
+
+### User Experience Requirements  
+- [ ] Intuitive interface requiring minimal user training
+- [ ] Clear progress indication and feedback
+- [ ] Responsive design that adapts to different screen sizes
+- [ ] Accessibility compliance for keyboard navigation
+- [ ] Professional visual design matching existing application theme
+
+### Technical Requirements
+- [ ] Robust error handling with detailed logging
+- [ ] Atomic file operations with rollback capability
+- [ ] Efficient memory usage during batch operations
+- [ ] Integration with existing download queue system
+- [ ] Maintainable code architecture for future enhancements
 
 ## Key Components Status
 
diff --git a/SPOTIFY_MATCHING_SPEC.md b/SPOTIFY_MATCHING_SPEC.md
new file mode 100644
index 00000000..2c18bf6e
--- /dev/null
+++ b/SPOTIFY_MATCHING_SPEC.md
@@ -0,0 +1,907 @@
+# Spotify Matched Download System - Technical Specification
+
+## 📋 Document Purpose
+This document provides comprehensive technical specifications for implementing the Spotify Matched Download System. It addresses the complexity of music metadata matching, file organization, and user interface design based on real-world challenges and requirements.
+
+---
+
+## 🏗️ System Architecture Overview
+
+### Core Components
+```
+┌─────────────────────────────────────────────────────────────────┐
+│                     Spotify Matched Download System              │
+├─────────────────────────────────────────────────────────────────┤
+│  UI Layer                                                       │
+│  ┌─────────────────┐  ┌─────────────────┐  ┌─────────────────┐ │
+│  │ Matched Download│  │  Matching Modal │  │ Progress Tracking│ │
+│  │     Buttons     │  │                 │  │                 │ │
+│  └─────────────────┘  └─────────────────┘  └─────────────────┘ │
+├─────────────────────────────────────────────────────────────────┤
+│  Service Layer                                                  │
+│  ┌─────────────────┐  ┌─────────────────┐  ┌─────────────────┐ │
+│  │ Metadata        │  │ Spotify Matching│  │ File Organization│ │
+│  │ Extraction      │  │    Service      │  │    Service      │ │
+│  └─────────────────┘  └─────────────────┘  └─────────────────┘ │
+├─────────────────────────────────────────────────────────────────┤
+│  Integration Layer                                              │
+│  ┌─────────────────┐  ┌─────────────────┐  ┌─────────────────┐ │
+│  │   Soulseek      │  │    Spotify      │  │   File System   │ │
+│  │    Client       │  │     Client      │  │    Manager      │ │
+│  └─────────────────┘  └─────────────────┘  └─────────────────┘ │
+└─────────────────────────────────────────────────────────────────┘
+```
+
+---
+
+## 🔍 Advanced Metadata Extraction System
+
+### Problem Statement
+Soulseek metadata is notoriously inconsistent:
+- Filenames: `"Track 01.mp3"`, `"asdjklh.flac"`, `"Artist - Song (Remix).mp3"`
+- Directory paths: `"/User/Music/Random Folder/"`
+- Missing or incorrect artist/title/album information
+
+### Solution: Multi-Tier Extraction Strategy
+
+#### Tier 1: Leverage Existing TrackResult Fields (PRIMARY)
+```python
+class EnhancedMetadataExtractor:
+    def extract_from_track_result(self, track: TrackResult) -> TrackMetadata:
+        """
+        Primary extraction using existing TrackResult fields.
+        These are already parsed by soulseek_client.py
+        """
+        return TrackMetadata(
+            artist=track.artist,           # Already extracted!
+            title=track.title,             # Already extracted!
+            album=track.album,             # Already extracted!
+            track_number=track.track_number, # Already extracted!
+            filename=track.filename,
+            confidence=self.calculate_field_confidence(track)
+        )
+```
+
+#### Tier 2: Enhanced Filename Parsing (SECONDARY)
+```python
+class AdvancedFilenameParser:
+    PATTERNS = [
+        # Pattern: "Artist - Title"
+        r'^(?P<artist>.+?)\s*[-–—]\s*(?P<title>.+?)(?:\s*\[(?P<extra>.*?)\])?(?:\s*\((?P<remix>.*?[Rr]emix.*?)\))?$',
+        
+        # Pattern: "01 - Artist - Title"  
+        r'^(?P<track>\d+)\s*[-\.]\s*(?P<artist>.+?)\s*[-–—]\s*(?P<title>.+?)(?:\s*\((?P<remix>.*?)\))?$',
+        
+        # Pattern: "Artist - Album - Title"
+        r'^(?P<artist>.+?)\s*[-–—]\s*(?P<album>.+?)\s*[-–—]\s*(?P<title>.+?)$',
+        
+        # Pattern: "Title (Artist Remix)"
+        r'^(?P<title>.+?)\s*\((?P<remix_artist>.+?)\s+[Rr]emix\)$',
+        
+        # Pattern: "Album - Track - Title"
+        r'^(?P<album>.+?)\s*[-–—]\s*(?P<track>\d+)\s*[-–—]\s*(?P<title>.+?)$'
+    ]
+    
+    def parse_filename(self, filename: str) -> Optional[TrackMetadata]:
+        """Enhanced filename parsing with remix detection"""
+        base_name = self.clean_filename(filename)
+        
+        for pattern in self.PATTERNS:
+            match = re.match(pattern, base_name, re.IGNORECASE)
+            if match:
+                return self.create_metadata_from_match(match)
+        
+        return None
+```
+
+#### Tier 3: Directory Context Analysis (TERTIARY)
+```python
+class DirectoryContextAnalyzer:
+    def analyze_path_context(self, filepath: str) -> Optional[AlbumContext]:
+        """
+        Extract album context from directory structure
+        Example: "/Music/Artist/Album (Year)/Track.flac"
+        """
+        path_parts = Path(filepath).parts
+        
+        # Common patterns for album directories
+        album_patterns = [
+            r'(?P<artist>.+?)\s*[-–—]\s*(?P<album>.+?)(?:\s*\((?P<year>\d{4})\))?',
+            r'(?P<album>.+?)(?:\s*\((?P<year>\d{4})\))?',
+            r'\[(?P<year>\d{4})\]\s*(?P<album>.+?)'
+        ]
+        
+        # Analyze parent directories for album info
+        for part in reversed(path_parts):
+            for pattern in album_patterns:
+                match = re.match(pattern, part, re.IGNORECASE)
+                if match:
+                    return AlbumContext(**match.groupdict())
+        
+        return None
+```
+
+---
+
+## 🎵 Sophisticated Matching Algorithms
+
+### Multi-Stage Matching Pipeline
+
+#### Stage 1: Exact Match Strategy
+```python
+class ExactMatcher:
+    def find_exact_match(self, metadata: TrackMetadata) -> List[SpotifyMatch]:
+        """
+        Highest confidence matching with exact metadata
+        """
+        if not (metadata.artist and metadata.title):
+            return []
+        
+        # Build exact search query
+        query_parts = []
+        if metadata.artist:
+            query_parts.append(f'artist:"{metadata.artist}"')
+        if metadata.title:
+            query_parts.append(f'track:"{metadata.title}"')
+        if metadata.album:
+            query_parts.append(f'album:"{metadata.album}"')
+        
+        query = ' '.join(query_parts)
+        results = self.spotify_client.search_tracks(query, limit=5)
+        
+        return [SpotifyMatch(track, confidence=0.95) for track in results[:3]]
+```
+
+#### Stage 2: Fuzzy Match Strategy
+```python
+class FuzzyMatcher:
+    def find_fuzzy_matches(self, metadata: TrackMetadata) -> List[SpotifyMatch]:
+        """
+        Similarity-based matching with confidence scoring
+        """
+        # Normalize strings for comparison
+        normalized_artist = self.normalize_string(metadata.artist)
+        normalized_title = self.normalize_string(metadata.title)
+        
+        # Generate search variations
+        search_queries = [
+            f"{normalized_artist} {normalized_title}",
+            f"{metadata.artist} {metadata.title}",  # Original strings
+            f'"{normalized_artist}" "{normalized_title}"',  # Quoted search
+        ]
+        
+        all_matches = []
+        for query in search_queries:
+            results = self.spotify_client.search_tracks(query, limit=10)
+            for track in results:
+                confidence = self.calculate_similarity_confidence(metadata, track)
+                if confidence >= 0.6:  # Minimum threshold
+                    all_matches.append(SpotifyMatch(track, confidence))
+        
+        # Deduplicate and sort by confidence
+        return self.deduplicate_matches(all_matches)
+    
+    def calculate_similarity_confidence(self, metadata: TrackMetadata, spotify_track: SpotifyTrack) -> float:
+        """
+        Advanced confidence calculation with multiple factors
+        """
+        # Artist similarity (weight: 40%)
+        artist_sim = self.string_similarity(
+            self.normalize_string(metadata.artist),
+            self.normalize_string(spotify_track.artists[0])
+        )
+        
+        # Title similarity (weight: 50%)
+        title_sim = self.string_similarity(
+            self.normalize_string(metadata.title),
+            self.normalize_string(spotify_track.name)
+        )
+        
+        # Album similarity (weight: 10%)
+        album_sim = 0.0
+        if metadata.album and spotify_track.album:
+            album_sim = self.string_similarity(
+                self.normalize_string(metadata.album),
+                self.normalize_string(spotify_track.album)
+            )
+        
+        # Duration similarity bonus (weight: bonus +5%)
+        duration_bonus = 0.0
+        if metadata.duration and spotify_track.duration_ms:
+            duration_diff = abs(metadata.duration - (spotify_track.duration_ms / 1000))
+            if duration_diff <= 5:  # Within 5 seconds
+                duration_bonus = 0.05
+        
+        confidence = (artist_sim * 0.4) + (title_sim * 0.5) + (album_sim * 0.1) + duration_bonus
+        return min(confidence, 1.0)
+```
+
+#### Stage 3: Remix Detection & Handling
+```python
+class RemixMatcher:
+    REMIX_PATTERNS = [
+        r'(?P<title>.+?)\s*\((?P<remix_artist>.+?)\s+[Rr]emix\)',
+        r'(?P<title>.+?)\s*\[(?P<remix_artist>.+?)\s+[Rr]emix\]',
+        r'(?P<title>.+?)\s*-\s*(?P<remix_artist>.+?)\s+[Rr]emix',
+        r'(?P<title>.+?)\s+\((?P<remix_artist>.+?)\s+[Vv]ersion\)',
+    ]
+    
+    def detect_remix(self, title: str) -> Optional[RemixInfo]:
+        """
+        Extract remix information from track title
+        """
+        for pattern in self.REMIX_PATTERNS:
+            match = re.search(pattern, title, re.IGNORECASE)
+            if match:
+                return RemixInfo(
+                    original_title=match.group('title').strip(),
+                    remix_artist=match.group('remix_artist').strip(),
+                    is_remix=True
+                )
+        return None
+    
+    def match_remix_track(self, metadata: TrackMetadata, remix_info: RemixInfo) -> List[SpotifyMatch]:
+        """
+        Search for remix tracks with proper artist attribution
+        """
+        search_queries = [
+            f'artist:"{remix_info.remix_artist}" track:"{remix_info.original_title}"',
+            f'"{remix_info.remix_artist}" "{remix_info.original_title}" remix',
+            f'"{remix_info.original_title}" "{remix_info.remix_artist}"'
+        ]
+        
+        matches = []
+        for query in search_queries:
+            results = self.spotify_client.search_tracks(query, limit=5)
+            for track in results:
+                # Prioritize tracks where remix artist is primary artist
+                if remix_info.remix_artist.lower() in [a.lower() for a in track.artists]:
+                    confidence = 0.85  # High confidence for proper remix attribution
+                    matches.append(SpotifyMatch(track, confidence, match_type="remix"))
+        
+        return matches
+```
+
+---
+
+## 🎨 Professional UI Architecture
+
+### Responsive Modal Design
+
+#### Problem with Previous Implementation
+- "Squished" content with poor spacing
+- Inflexible layouts that didn't adapt to content
+- Poor user experience with cramped interface
+
+#### Solution: Professional Modal Architecture
+```python
+class ResponsiveMatchingModal(QDialog):
+    """
+    Professional modal with responsive design and proper spacing
+    """
+    
+    def __init__(self, parent=None):
+        super().__init__(parent)
+        self.setup_responsive_ui()
+    
+    def setup_responsive_ui(self):
+        """
+        Create responsive layout with proper spacing and sizing
+        """
+        # Modal sizing - responsive to screen size
+        screen = QApplication.primaryScreen().geometry()
+        modal_width = min(900, int(screen.width() * 0.7))   # 70% of screen width, max 900px
+        modal_height = min(700, int(screen.height() * 0.8)) # 80% of screen height, max 700px
+        
+        self.resize(modal_width, modal_height)
+        self.setMinimumSize(600, 500)  # Minimum usable size
+        
+        # Center on parent/screen
+        self.center_on_parent()
+        
+        # Main layout with proper margins
+        main_layout = QVBoxLayout(self)
+        main_layout.setContentsMargins(24, 24, 24, 24)  # Generous margins
+        main_layout.setSpacing(20)  # Proper spacing between sections
+        
+        # Create sections
+        self.create_header_section(main_layout)
+        self.create_progress_section(main_layout)
+        self.create_results_section(main_layout)
+        self.create_manual_search_section(main_layout)
+        self.create_action_buttons_section(main_layout)
+    
+    def create_header_section(self, parent_layout):
+        """
+        Track information header with proper typography
+        """
+        header_frame = QFrame()
+        header_frame.setStyleSheet("""
+            QFrame {
+                background: rgba(30, 30, 30, 0.9);
+                border-radius: 12px;
+                padding: 20px;
+            }
+        """)
+        
+        header_layout = QVBoxLayout(header_frame)
+        header_layout.setSpacing(12)
+        
+        # Title with proper typography
+        title = QLabel("🎯 Spotify Track Matching")
+        title.setStyleSheet("""
+            QLabel {
+                font-size: 22px;
+                font-weight: bold;
+                color: #1db954;
+                margin-bottom: 8px;
+            }
+        """)
+        
+        # Track info with readable formatting
+        track_info_layout = QGridLayout()
+        track_info_layout.setColumnStretch(1, 1)  # Second column expands
+        
+        # Add track details with proper alignment
+        self.add_info_row(track_info_layout, 0, "Track:", self.track_metadata.title)
+        self.add_info_row(track_info_layout, 1, "Artist:", self.track_metadata.artist)
+        self.add_info_row(track_info_layout, 2, "Album:", self.track_metadata.album or "Unknown")
+        
+        header_layout.addWidget(title)
+        header_layout.addLayout(track_info_layout)
+        parent_layout.addWidget(header_frame)
+    
+    def create_results_section(self, parent_layout):
+        """
+        Results section with proper scrolling and spacing
+        """
+        results_frame = QFrame()
+        results_frame.setStyleSheet("""
+            QFrame {
+                background: rgba(40, 40, 40, 0.9);
+                border-radius: 12px;
+                padding: 20px;
+            }
+        """)
+        
+        results_layout = QVBoxLayout(results_frame)
+        results_layout.setSpacing(16)
+        
+        # Section title
+        results_title = QLabel("🎵 Automatic Match Results")
+        results_title.setStyleSheet("""
+            QLabel {
+                font-size: 18px;
+                font-weight: bold;
+                color: white;
+                margin-bottom: 10px;
+            }
+        """)
+        
+        # Scrollable results area
+        scroll_area = QScrollArea()
+        scroll_area.setWidgetResizable(True)
+        scroll_area.setHorizontalScrollBarPolicy(Qt.ScrollBarPolicy.ScrollBarNever)
+        scroll_area.setVerticalScrollBarPolicy(Qt.ScrollBarPolicy.ScrollBarAsNeeded)
+        scroll_area.setMinimumHeight(200)  # Ensure minimum visible area
+        scroll_area.setStyleSheet("""
+            QScrollArea {
+                border: none;
+                background: transparent;
+            }
+            QScrollBar:vertical {
+                background: rgba(60, 60, 60, 0.5);
+                width: 12px;
+                border-radius: 6px;
+            }
+            QScrollBar::handle:vertical {
+                background: rgba(29, 185, 84, 0.8);
+                border-radius: 6px;
+                min-height: 20px;
+            }
+        """)
+        
+        # Results container
+        self.results_container = QWidget()
+        self.results_layout = QVBoxLayout(self.results_container)
+        self.results_layout.setSpacing(12)  # Proper spacing between result items
+        self.results_layout.setContentsMargins(0, 0, 0, 0)
+        
+        scroll_area.setWidget(self.results_container)
+        
+        results_layout.addWidget(results_title)
+        results_layout.addWidget(scroll_area, 1)  # Expand to fill space
+        
+        parent_layout.addWidget(results_frame, 1)  # Allow results section to expand
+```
+
+#### Individual Result Item Design
+```python
+class SpotifyMatchResultItem(QFrame):
+    """
+    Individual Spotify match result with professional styling
+    """
+    
+    def __init__(self, spotify_track: SpotifyTrack, confidence: float, parent=None):
+        super().__init__(parent)
+        self.spotify_track = spotify_track
+        self.confidence = confidence
+        self.setup_professional_ui()
+    
+    def setup_professional_ui(self):
+        """
+        Create professional result item with proper spacing
+        """
+        self.setFixedHeight(100)  # Consistent height for all items
+        self.setStyleSheet("""
+            QFrame {
+                background: rgba(50, 50, 50, 0.8);
+                border: 1px solid rgba(80, 80, 80, 0.6);
+                border-radius: 10px;
+                margin: 4px 0px;
+            }
+            QFrame:hover {
+                background: rgba(60, 60, 60, 0.9);
+                border-color: rgba(29, 185, 84, 0.8);
+            }
+        """)
+        
+        layout = QHBoxLayout(self)
+        layout.setContentsMargins(16, 12, 16, 12)  # Proper margins
+        layout.setSpacing(16)  # Good spacing between elements
+        
+        # Left section: Track info
+        info_layout = QVBoxLayout()
+        info_layout.setSpacing(4)
+        
+        # Track title
+        title_label = QLabel(spotify_track.name)
+        title_label.setStyleSheet("""
+            QLabel {
+                font-size: 16px;
+                font-weight: bold;
+                color: white;
+            }
+        """)
+        title_label.setWordWrap(True)
+        
+        # Artist and album
+        artist_text = ", ".join(spotify_track.artists)
+        details_label = QLabel(f"by {artist_text}")
+        details_label.setStyleSheet("""
+            QLabel {
+                font-size: 13px;
+                color: rgba(255, 255, 255, 0.8);
+            }
+        """)
+        
+        album_label = QLabel(f"from {spotify_track.album}")
+        album_label.setStyleSheet("""
+            QLabel {
+                font-size: 12px;
+                color: rgba(255, 255, 255, 0.6);
+            }
+        """)
+        
+        info_layout.addWidget(title_label)
+        info_layout.addWidget(details_label)
+        info_layout.addWidget(album_label)
+        
+        # Right section: Confidence and select button
+        right_layout = QVBoxLayout()
+        right_layout.setAlignment(Qt.AlignmentFlag.AlignTop)
+        
+        # Confidence indicator
+        confidence_widget = self.create_confidence_widget()
+        
+        # Select button
+        select_button = QPushButton("Select This Track")
+        select_button.setStyleSheet("""
+            QPushButton {
+                background: qlineargradient(x1:0, y1:0, x2:0, y2:1,
+                    stop:0 rgba(29, 185, 84, 0.9),
+                    stop:1 rgba(25, 156, 71, 0.9));
+                color: white;
+                border: none;
+                border-radius: 6px;
+                padding: 8px 16px;
+                font-weight: bold;
+                font-size: 13px;
+            }
+            QPushButton:hover {
+                background: qlineargradient(x1:0, y1:0, x2:0, y2:1,
+                    stop:0 rgba(32, 200, 90, 1.0),
+                    stop:1 rgba(28, 170, 76, 1.0));
+            }
+        """)
+        select_button.clicked.connect(self.on_select_clicked)
+        
+        right_layout.addWidget(confidence_widget)
+        right_layout.addStretch()
+        right_layout.addWidget(select_button)
+        
+        # Assembly
+        layout.addLayout(info_layout, 1)  # Expand info section
+        layout.addLayout(right_layout)
+    
+    def create_confidence_widget(self) -> QWidget:
+        """
+        Create professional confidence indicator
+        """
+        confidence_widget = QFrame()
+        confidence_widget.setFixedSize(60, 60)
+        
+        # Color based on confidence level
+        if self.confidence >= 0.9:
+            color = "#28a745"  # Green
+            text_color = "white"
+        elif self.confidence >= 0.75:
+            color = "#ffc107"  # Yellow  
+            text_color = "black"
+        elif self.confidence >= 0.6:
+            color = "#fd7e14"  # Orange
+            text_color = "white"
+        else:
+            color = "#dc3545"  # Red
+            text_color = "white"
+        
+        confidence_widget.setStyleSheet(f"""
+            QFrame {{
+                background: {color};
+                border-radius: 30px;
+                border: 2px solid rgba(255, 255, 255, 0.2);
+            }}
+        """)
+        
+        layout = QVBoxLayout(confidence_widget)
+        layout.setContentsMargins(0, 0, 0, 0)
+        
+        percentage_label = QLabel(f"{int(self.confidence * 100)}%")
+        percentage_label.setAlignment(Qt.AlignmentFlag.AlignCenter)
+        percentage_label.setStyleSheet(f"""
+            QLabel {{
+                color: {text_color};
+                font-size: 14px;
+                font-weight: bold;
+            }}
+        """)
+        
+        layout.addWidget(percentage_label)
+        
+        return confidence_widget
+```
+
+---
+
+## 📁 Professional File Organization System
+
+### Atomic File Operations
+```python
+class AtomicFileOrganizer:
+    """
+    Professional file organization with rollback capability
+    """
+    
+    def __init__(self, transfer_base_path: str = "Transfer"):
+        self.transfer_base_path = Path(transfer_base_path)
+        self.operation_log = []  # Track operations for rollback
+    
+    def organize_file(self, source_path: str, spotify_track: SpotifyTrack) -> FileOrganizationResult:
+        """
+        Atomically organize file with full rollback capability
+        """
+        try:
+            # Phase 1: Validation
+            source_file = Path(source_path)
+            if not source_file.exists():
+                return FileOrganizationResult(
+                    success=False,
+                    error="Source file does not exist",
+                    source_path=source_path
+                )
+            
+            # Phase 2: Destination planning
+            destination_path = self.calculate_destination_path(spotify_track, source_file.suffix)
+            
+            # Phase 3: Conflict resolution
+            final_destination = self.resolve_conflicts(destination_path)
+            
+            # Phase 4: Atomic operation
+            return self.perform_atomic_move(source_file, final_destination)
+            
+        except Exception as e:
+            return FileOrganizationResult(
+                success=False,
+                error=f"Organization failed: {str(e)}",
+                source_path=source_path
+            )
+    
+    def calculate_destination_path(self, spotify_track: SpotifyTrack, file_extension: str) -> Path:
+        """
+        Calculate organized file path following professional naming conventions
+        """
+        # Sanitize names for filesystem compatibility
+        artist_name = self.sanitize_filename(spotify_track.artists[0])
+        album_name = self.sanitize_filename(spotify_track.album)
+        track_name = self.sanitize_filename(spotify_track.name)
+        
+        # Handle multi-artist tracks
+        if len(spotify_track.artists) > 1:
+            primary_artist = spotify_track.artists[0]
+            # Keep featured artists in track name
+            if "feat." in track_name.lower() or "featuring" in track_name.lower():
+                final_track_name = f"{primary_artist} - {track_name}"
+            else:
+                featured_artists = ", ".join(spotify_track.artists[1:])
+                final_track_name = f"{primary_artist} - {track_name} (feat. {featured_artists})"
+        else:
+            final_track_name = f"{artist_name} - {track_name}"
+        
+        # Create path structure
+        artist_folder = artist_name
+        album_folder = f"{artist_name} - {album_name}"
+        filename = f"{final_track_name}{file_extension}"
+        
+        return self.transfer_base_path / artist_folder / album_folder / filename
+    
+    def resolve_conflicts(self, destination_path: Path) -> Path:
+        """
+        Handle file naming conflicts professionally
+        """
+        if not destination_path.exists():
+            return destination_path
+        
+        # Generate unique filename
+        base_path = destination_path.parent / destination_path.stem
+        extension = destination_path.suffix
+        counter = 1
+        
+        while True:
+            new_path = Path(f"{base_path} ({counter}){extension}")
+            if not new_path.exists():
+                return new_path
+            counter += 1
+            
+            # Safety limit
+            if counter > 100:
+                raise Exception("Too many file conflicts")
+    
+    def perform_atomic_move(self, source: Path, destination: Path) -> FileOrganizationResult:
+        """
+        Perform atomic file move with backup and rollback
+        """
+        operation_id = str(uuid.uuid4())
+        
+        try:
+            # Ensure destination directory exists
+            destination.parent.mkdir(parents=True, exist_ok=True)
+            
+            # Create backup if destination exists
+            backup_path = None
+            if destination.exists():
+                backup_path = destination.with_suffix(f".backup_{operation_id}")
+                shutil.copy2(destination, backup_path)
+                self.operation_log.append({
+                    'operation_id': operation_id,
+                    'type': 'backup',
+                    'path': backup_path
+                })
+            
+            # Perform the move
+            shutil.move(str(source), str(destination))
+            self.operation_log.append({
+                'operation_id': operation_id,
+                'type': 'move',
+                'source': str(source),
+                'destination': str(destination)
+            })
+            
+            # Cleanup backup on success
+            if backup_path and backup_path.exists():
+                backup_path.unlink()
+            
+            return FileOrganizationResult(
+                success=True,
+                source_path=str(source),
+                destination_path=str(destination),
+                operation_id=operation_id
+            )
+            
+        except Exception as e:
+            # Rollback on failure
+            self.rollback_operation(operation_id)
+            return FileOrganizationResult(
+                success=False,
+                error=f"File move failed: {str(e)}",
+                source_path=str(source)
+            )
+    
+    def sanitize_filename(self, name: str) -> str:
+        """
+        Sanitize filename for cross-platform compatibility
+        """
+        # Remove/replace invalid characters
+        invalid_chars = r'<>:"/\|?*'
+        for char in invalid_chars:
+            name = name.replace(char, '')
+        
+        # Handle special cases
+        name = name.replace('..', '.')  # Double dots
+        name = re.sub(r'\s+', ' ', name)  # Multiple spaces
+        name = name.strip(' .')  # Leading/trailing spaces and dots
+        
+        # Length limit
+        if len(name) > 200:
+            name = name[:200].rsplit(' ', 1)[0]  # Break at word boundary
+        
+        return name or "Unknown"  # Fallback for empty names
+```
+
+---
+
+## 🔄 Integration with Existing Download System
+
+### Download Completion Detection
+```python
+class DownloadCompletionMonitor:
+    """
+    Monitor download completions and trigger matching process
+    """
+    
+    def __init__(self, download_manager, matching_service):
+        self.download_manager = download_manager
+        self.matching_service = matching_service
+        self.pending_matches = {}  # Track matched downloads
+    
+    def register_matched_download(self, search_result, track_metadata):
+        """
+        Register a download for post-completion matching
+        """
+        download_id = self.generate_download_id(search_result)
+        self.pending_matches[download_id] = {
+            'search_result': search_result,
+            'track_metadata': track_metadata,
+            'timestamp': time.time()
+        }
+    
+    def on_download_completed(self, download_item):
+        """
+        Handle download completion and trigger matching if needed
+        """
+        download_id = self.generate_download_id(download_item.search_result)
+        
+        if download_id in self.pending_matches:
+            # This was a matched download - trigger matching process
+            match_info = self.pending_matches[download_id]
+            self.trigger_post_download_matching(download_item, match_info)
+            del self.pending_matches[download_id]
+    
+    def trigger_post_download_matching(self, download_item, match_info):
+        """
+        Start matching process after download completion
+        """
+        # Update track metadata with actual download path
+        track_metadata = match_info['track_metadata']
+        track_metadata.file_path = download_item.local_path
+        
+        # Show matching modal
+        modal = MatchingModal(
+            matching_service=self.matching_service,
+            track_metadata=track_metadata,
+            download_path=download_item.local_path
+        )
+        modal.show()
+```
+
+---
+
+## 🧪 Testing Strategy
+
+### Unit Tests
+```python
+class TestMetadataExtraction:
+    """Test metadata extraction with real-world examples"""
+    
+    def test_common_filename_patterns(self):
+        test_cases = [
+            ("Artist - Song.mp3", {"artist": "Artist", "title": "Song"}),
+            ("01 - Artist - Song.flac", {"track": 1, "artist": "Artist", "title": "Song"}),
+            ("Song (Artist Remix).mp3", {"title": "Song", "remix_artist": "Artist"}),
+            ("Artist - Album - Song.mp3", {"artist": "Artist", "album": "Album", "title": "Song"}),
+        ]
+        
+        extractor = AdvancedFilenameParser()
+        for filename, expected in test_cases:
+            result = extractor.parse_filename(filename)
+            assert result.artist == expected.get("artist")
+            assert result.title == expected.get("title")
+
+class TestMatchingAlgorithms:
+    """Test matching accuracy with known examples"""
+    
+    def test_exact_matches(self):
+        """Test exact matching with perfect metadata"""
+        pass
+    
+    def test_fuzzy_matches(self):
+        """Test fuzzy matching with slight variations"""
+        pass
+    
+    def test_remix_detection(self):
+        """Test remix detection and proper artist attribution"""
+        pass
+
+class TestFileOrganization:
+    """Test file organization and conflict resolution"""
+    
+    def test_atomic_operations(self):
+        """Test atomic file moves with rollback"""
+        pass
+    
+    def test_conflict_resolution(self):
+        """Test handling of duplicate files"""
+        pass
+    
+    def test_cross_platform_compatibility(self):
+        """Test filename sanitization across platforms"""
+        pass
+```
+
+### Integration Tests
+```python
+class TestEndToEndWorkflow:
+    """Test complete matched download workflow"""
+    
+    def test_single_track_workflow(self):
+        """Test complete single track matched download"""
+        pass
+    
+    def test_error_handling_workflow(self):
+        """Test error scenarios and fallbacks"""
+        pass
+    
+    def test_ui_responsiveness(self):
+        """Test UI behavior under various conditions"""
+        pass
+```
+
+---
+
+## 📊 Performance Considerations
+
+### Optimization Strategies
+1. **Caching**: Cache Spotify search results to avoid duplicate API calls
+2. **Batch Processing**: Group multiple searches for efficiency
+3. **Lazy Loading**: Load UI elements as needed
+4. **Background Processing**: Perform heavy operations in separate threads
+5. **Memory Management**: Proper cleanup of modal dialogs and threads
+
+### Monitoring & Metrics
+- Track matching success rates
+- Monitor API response times
+- Log file organization errors
+- Measure user interaction patterns
+
+---
+
+## 🎯 Implementation Priorities
+
+### Phase 1: Core Foundation
+1. ✅ Enhanced metadata extraction system
+2. ✅ Basic matching algorithms
+3. ✅ File organization framework
+4. ✅ Professional UI architecture
+
+### Phase 2: Advanced Features
+1. Remix detection and handling
+2. Confidence scoring system
+3. Error handling and rollback
+4. Performance optimizations
+
+### Phase 3: Integration & Polish
+1. Download system integration
+2. Comprehensive testing
+3. User experience refinements
+4. Documentation and deployment
+
+This specification provides a comprehensive foundation for implementing a professional-grade Spotify matching system that addresses real-world complexity and user experience requirements.
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