diff --git a/allstarr/Controllers/AdminController.cs b/allstarr/Controllers/AdminController.cs
index 8b6c8d6..b7363b6 100644
--- a/allstarr/Controllers/AdminController.cs
+++ b/allstarr/Controllers/AdminController.cs
@@ -553,6 +553,56 @@ public class AdminController : ControllerBase
         }
     }
     
+    /// <summary>
+    /// Get track details by Jellyfin ID (for URL-based mapping)
+    /// </summary>
+    [HttpGet("jellyfin/track/{id}")]
+    public async Task<IActionResult> GetJellyfinTrack(string id)
+    {
+        if (string.IsNullOrWhiteSpace(id))
+        {
+            return BadRequest(new { error = "Track ID is required" });
+        }
+        
+        try
+        {
+            var url = $"{_jellyfinSettings.Url}/Items/{id}";
+            var request = new HttpRequestMessage(HttpMethod.Get, url);
+            request.Headers.Add("X-Emby-Authorization", GetJellyfinAuthHeader());
+            
+            var response = await _jellyfinHttpClient.SendAsync(request);
+            if (!response.IsSuccessStatusCode)
+            {
+                return StatusCode((int)response.StatusCode, new { error = "Track not found" });
+            }
+            
+            var json = await response.Content.ReadAsStringAsync();
+            using var doc = JsonDocument.Parse(json);
+            
+            var item = doc.RootElement;
+            var trackId = item.TryGetProperty("Id", out var idEl) ? idEl.GetString() : "";
+            var title = item.TryGetProperty("Name", out var nameEl) ? nameEl.GetString() : "";
+            var album = item.TryGetProperty("Album", out var albumEl) ? albumEl.GetString() : "";
+            var artist = "";
+            
+            if (item.TryGetProperty("Artists", out var artistsEl) && artistsEl.GetArrayLength() > 0)
+            {
+                artist = artistsEl[0].GetString() ?? "";
+            }
+            else if (item.TryGetProperty("AlbumArtist", out var albumArtistEl))
+            {
+                artist = albumArtistEl.GetString() ?? "";
+            }
+            
+            return Ok(new { id = trackId, title, artist, album });
+        }
+        catch (Exception ex)
+        {
+            _logger.LogError(ex, "Failed to get Jellyfin track {Id}", id);
+            return StatusCode(500, new { error = "Failed to get track details" });
+        }
+    }
+    
     /// <summary>
     /// Save manual track mapping
     /// </summary>
@@ -896,7 +946,7 @@ public class AdminController : ControllerBase
         }
         
         // Clear ALL Redis cache keys for Spotify playlists
-        // This includes matched tracks, ordered tracks, missing tracks, etc.
+        // This includes matched tracks, ordered tracks, missing tracks, playlist items, etc.
         foreach (var playlist in _spotifyImportSettings.Playlists)
         {
             var keysToDelete = new[]
@@ -904,7 +954,8 @@ public class AdminController : ControllerBase
                 $"spotify:playlist:{playlist.Name}",
                 $"spotify:missing:{playlist.Name}",
                 $"spotify:matched:{playlist.Name}",
-                $"spotify:matched:ordered:{playlist.Name}"
+                $"spotify:matched:ordered:{playlist.Name}",
+                $"spotify:playlist:items:{playlist.Name}"  // NEW: Clear file-backed playlist items cache
             };
             
             foreach (var key in keysToDelete)
@@ -917,7 +968,16 @@ public class AdminController : ControllerBase
             }
         }
         
-        _logger.LogInformation("Cache cleared: {Files} files, {RedisKeys} Redis keys", clearedFiles, clearedRedisKeys);
+        // Clear all search cache keys (pattern-based deletion)
+        var searchKeysDeleted = await _cache.DeleteByPatternAsync("search:*");
+        clearedRedisKeys += searchKeysDeleted;
+        
+        // Clear all image cache keys (pattern-based deletion)
+        var imageKeysDeleted = await _cache.DeleteByPatternAsync("image:*");
+        clearedRedisKeys += imageKeysDeleted;
+        
+        _logger.LogInformation("Cache cleared: {Files} files, {RedisKeys} Redis keys (including {SearchKeys} search keys, {ImageKeys} image keys)", 
+            clearedFiles, clearedRedisKeys, searchKeysDeleted, imageKeysDeleted);
         
         return Ok(new { 
             message = "Cache cleared successfully", 
diff --git a/allstarr/Controllers/JellyfinController.cs b/allstarr/Controllers/JellyfinController.cs
index b4d9a66..9d00358 100644
--- a/allstarr/Controllers/JellyfinController.cs
+++ b/allstarr/Controllers/JellyfinController.cs
@@ -102,6 +102,20 @@ public class JellyfinController : ControllerBase
         _logger.LogInformation("=== SEARCHITEMS V2 CALLED === searchTerm={SearchTerm}, includeItemTypes={ItemTypes}, parentId={ParentId}, artistIds={ArtistIds}, userId={UserId}", 
             searchTerm, includeItemTypes, parentId, artistIds, userId);
 
+        // Cache search results in Redis only (no file persistence, 15 min TTL)
+        // Only cache actual searches, not browse operations
+        if (!string.IsNullOrWhiteSpace(searchTerm) && string.IsNullOrWhiteSpace(artistIds))
+        {
+            var cacheKey = $"search:{searchTerm?.ToLowerInvariant()}:{includeItemTypes}:{limit}:{startIndex}";
+            var cachedResult = await _cache.GetAsync<object>(cacheKey);
+            
+            if (cachedResult != null)
+            {
+                _logger.LogDebug("✅ Returning cached search results for '{SearchTerm}'", searchTerm);
+                return new JsonResult(cachedResult);
+            }
+        }
+
         // If filtering by artist, handle external artists
         if (!string.IsNullOrWhiteSpace(artistIds))
         {
@@ -334,6 +348,14 @@ public class JellyfinController : ControllerBase
                 StartIndex = startIndex
             };
 
+            // Cache search results in Redis (15 min TTL, no file persistence)
+            if (!string.IsNullOrWhiteSpace(searchTerm) && string.IsNullOrWhiteSpace(artistIds))
+            {
+                var cacheKey = $"search:{searchTerm?.ToLowerInvariant()}:{includeItemTypes}:{limit}:{startIndex}";
+                await _cache.SetAsync(cacheKey, response, TimeSpan.FromMinutes(15));
+                _logger.LogDebug("💾 Cached search results for '{SearchTerm}' (15 min TTL)", searchTerm);
+            }
+
             _logger.LogInformation("About to serialize response...");
 
             var json = System.Text.Json.JsonSerializer.Serialize(response, new System.Text.Json.JsonSerializerOptions
@@ -2931,6 +2953,41 @@ public class JellyfinController : ControllerBase
     /// </summary>
     private async Task<IActionResult?> GetSpotifyPlaylistTracksOrderedAsync(string spotifyPlaylistName, string playlistId)
     {
+        // Check Redis cache first for fast serving
+        var cacheKey = $"spotify:playlist:items:{spotifyPlaylistName}";
+        var cachedItems = await _cache.GetAsync<List<Dictionary<string, object?>>>(cacheKey);
+        
+        if (cachedItems != null && cachedItems.Count > 0)
+        {
+            _logger.LogInformation("✅ Loaded {Count} playlist items from Redis cache for {Playlist}", 
+                cachedItems.Count, spotifyPlaylistName);
+            
+            return new JsonResult(new
+            {
+                Items = cachedItems,
+                TotalRecordCount = cachedItems.Count,
+                StartIndex = 0
+            });
+        }
+        
+        // Check file cache as fallback
+        var fileItems = await LoadPlaylistItemsFromFile(spotifyPlaylistName);
+        if (fileItems != null && fileItems.Count > 0)
+        {
+            _logger.LogInformation("✅ Loaded {Count} playlist items from file cache for {Playlist}", 
+                fileItems.Count, spotifyPlaylistName);
+            
+            // Restore to Redis cache
+            await _cache.SetAsync(cacheKey, fileItems, TimeSpan.FromHours(24));
+            
+            return new JsonResult(new
+            {
+                Items = fileItems,
+                TotalRecordCount = fileItems.Count,
+                StartIndex = 0
+            });
+        }
+        
         // Check for ordered matched tracks from SpotifyTrackMatchingService
         var orderedCacheKey = $"spotify:matched:ordered:{spotifyPlaylistName}";
         var orderedTracks = await _cache.GetAsync<List<MatchedTrack>>(orderedCacheKey);
@@ -3094,6 +3151,12 @@ public class JellyfinController : ControllerBase
             "🎵 Final playlist '{Playlist}': {Total} tracks ({Local} LOCAL + {External} EXTERNAL)", 
             spotifyPlaylistName, finalItems.Count, localUsedCount, externalUsedCount);
         
+        // Save to file cache for persistence across restarts
+        await SavePlaylistItemsToFile(spotifyPlaylistName, finalItems);
+        
+        // Also cache in Redis for fast serving (reuse the same cache key from top of method)
+        await _cache.SetAsync(cacheKey, finalItems, TimeSpan.FromHours(24));
+        
         // Return raw Jellyfin response format
         return new JsonResult(new
         {
@@ -3482,6 +3545,74 @@ public class JellyfinController : ControllerBase
         }
     }
 
+    /// <summary>
+    /// Saves playlist items (raw Jellyfin JSON) to file cache for persistence across restarts.
+    /// </summary>
+    private async Task SavePlaylistItemsToFile(string playlistName, List<Dictionary<string, object?>> items)
+    {
+        try
+        {
+            var cacheDir = "/app/cache/spotify";
+            Directory.CreateDirectory(cacheDir);
+            
+            var safeName = string.Join("_", playlistName.Split(Path.GetInvalidFileNameChars()));
+            var filePath = Path.Combine(cacheDir, $"{safeName}_items.json");
+            
+            var json = JsonSerializer.Serialize(items, new JsonSerializerOptions { WriteIndented = true });
+            await System.IO.File.WriteAllTextAsync(filePath, json);
+            
+            _logger.LogInformation("💾 Saved {Count} playlist items to file cache for {Playlist}", 
+                items.Count, playlistName);
+        }
+        catch (Exception ex)
+        {
+            _logger.LogError(ex, "Failed to save playlist items to file for {Playlist}", playlistName);
+        }
+    }
+
+    /// <summary>
+    /// Loads playlist items (raw Jellyfin JSON) from file cache.
+    /// </summary>
+    private async Task<List<Dictionary<string, object?>>?> LoadPlaylistItemsFromFile(string playlistName)
+    {
+        try
+        {
+            var safeName = string.Join("_", playlistName.Split(Path.GetInvalidFileNameChars()));
+            var filePath = Path.Combine("/app/cache/spotify", $"{safeName}_items.json");
+            
+            if (!System.IO.File.Exists(filePath))
+            {
+                _logger.LogDebug("No playlist items file cache found for {Playlist} at {Path}", playlistName, filePath);
+                return null;
+            }
+            
+            var fileAge = DateTime.UtcNow - System.IO.File.GetLastWriteTimeUtc(filePath);
+            
+            // Check if cache is too old (more than 24 hours)
+            if (fileAge.TotalHours > 24)
+            {
+                _logger.LogInformation("Playlist items file cache for {Playlist} is too old ({Age:F1}h), will rebuild", 
+                    playlistName, fileAge.TotalHours);
+                return null;
+            }
+            
+            _logger.LogDebug("Playlist items file cache for {Playlist} age: {Age:F1}h", playlistName, fileAge.TotalHours);
+            
+            var json = await System.IO.File.ReadAllTextAsync(filePath);
+            var items = JsonSerializer.Deserialize<List<Dictionary<string, object?>>>(json);
+            
+            _logger.LogInformation("💿 Loaded {Count} playlist items from file cache for {Playlist} (age: {Age:F1}h)", 
+                items?.Count ?? 0, playlistName, fileAge.TotalHours);
+            
+            return items;
+        }
+        catch (Exception ex)
+        {
+            _logger.LogWarning(ex, "Failed to load playlist items from file for {Playlist}", playlistName);
+            return null;
+        }
+    }
+
     /// <summary>
     /// Manual trigger endpoint to force fetch Spotify missing tracks.
     /// GET /spotify/sync?api_key=YOUR_KEY
diff --git a/allstarr/Services/Common/FuzzyMatcher.cs b/allstarr/Services/Common/FuzzyMatcher.cs
index 92664f0..1615994 100644
--- a/allstarr/Services/Common/FuzzyMatcher.cs
+++ b/allstarr/Services/Common/FuzzyMatcher.cs
@@ -16,8 +16,8 @@ public static class FuzzyMatcher
             return 0;
         }
 
-        var queryLower = query.ToLowerInvariant().Trim();
-        var targetLower = target.ToLowerInvariant().Trim();
+        var queryLower = NormalizeForMatching(query);
+        var targetLower = NormalizeForMatching(target);
 
         // Exact match
         if (queryLower == targetLower)
@@ -58,6 +58,34 @@ public static class FuzzyMatcher
         var similarity = (1.0 - (double)distance / maxLength) * 60;
         return (int)Math.Max(0, similarity);
     }
+    
+    /// <summary>
+    /// Normalizes a string for matching by:
+    /// - Converting to lowercase
+    /// - Normalizing apostrophes (', ', ') to standard '
+    /// - Removing extra whitespace
+    /// </summary>
+    private static string NormalizeForMatching(string text)
+    {
+        if (string.IsNullOrWhiteSpace(text))
+        {
+            return string.Empty;
+        }
+        
+        var normalized = text.ToLowerInvariant().Trim();
+        
+        // Normalize different apostrophe types to standard apostrophe
+        normalized = normalized
+            .Replace(''', '\'')  // Right single quotation mark
+            .Replace(''', '\'')  // Left single quotation mark
+            .Replace('`', '\'')  // Grave accent
+            .Replace('´', '\''); // Acute accent
+        
+        // Normalize whitespace
+        normalized = System.Text.RegularExpressions.Regex.Replace(normalized, @"\s+", " ");
+        
+        return normalized;
+    }
 
     /// <summary>
     /// Calculates Levenshtein distance between two strings.
diff --git a/allstarr/Services/Common/RedisCacheService.cs b/allstarr/Services/Common/RedisCacheService.cs
index 84cc9fd..5148a0e 100644
--- a/allstarr/Services/Common/RedisCacheService.cs
+++ b/allstarr/Services/Common/RedisCacheService.cs
@@ -168,4 +168,34 @@ public class RedisCacheService
             return false;
         }
     }
+
+    /// <summary>
+    /// Deletes all keys matching a pattern (e.g., "search:*").
+    /// WARNING: Use with caution as this scans all keys.
+    /// </summary>
+    public async Task<int> DeleteByPatternAsync(string pattern)
+    {
+        if (!IsEnabled) return 0;
+
+        try
+        {
+            var server = _redis!.GetServer(_redis.GetEndPoints().First());
+            var keys = server.Keys(pattern: pattern).ToArray();
+            
+            if (keys.Length == 0)
+            {
+                _logger.LogDebug("No keys found matching pattern: {Pattern}", pattern);
+                return 0;
+            }
+
+            var deleted = await _db!.KeyDeleteAsync(keys);
+            _logger.LogInformation("Deleted {Count} Redis keys matching pattern: {Pattern}", deleted, pattern);
+            return (int)deleted;
+        }
+        catch (Exception ex)
+        {
+            _logger.LogWarning(ex, "Redis DELETE BY PATTERN failed for pattern: {Pattern}", pattern);
+            return 0;
+        }
+    }
 }
diff --git a/allstarr/wwwroot/index.html b/allstarr/wwwroot/index.html
index 28e2a3d..b9b40bc 100644
--- a/allstarr/wwwroot/index.html
+++ b/allstarr/wwwroot/index.html
@@ -873,11 +873,22 @@
             </div>
             <div class="form-group">
                 <label>Search Jellyfin Tracks</label>
-                <input type="text" id="map-search-query" placeholder="Search by title or artist..." oninput="searchJellyfinTracks()">
+                <input type="text" id="map-search-query" placeholder="Search by title, artist, or album..." oninput="searchJellyfinTracks()">
+                <small style="color: var(--text-secondary); display: block; margin-top: 4px;">
+                    Tip: Use commas to search multiple terms (e.g., "It Ain't Easy, David Bowie")
+                </small>
+            </div>
+            <div style="text-align: center; color: var(--text-secondary); margin: 12px 0;">— OR —</div>
+            <div class="form-group">
+                <label>Paste Jellyfin Track URL</label>
+                <input type="text" id="map-jellyfin-url" placeholder="https://jellyfin.example.com/web/#/details?id=..." oninput="extractJellyfinId()">
+                <small style="color: var(--text-secondary); display: block; margin-top: 4px;">
+                    Paste the full URL from your Jellyfin web interface
+                </small>
             </div>
             <div id="map-search-results" style="max-height: 300px; overflow-y: auto; margin-top: 12px;">
                 <p style="text-align: center; color: var(--text-secondary); padding: 20px;">
-                    Type to search for local tracks...
+                    Type to search for local tracks or paste a Jellyfin URL...
                 </p>
             </div>
             <input type="hidden" id="map-playlist-name">
@@ -1757,10 +1768,13 @@
             const query = document.getElementById('map-search-query').value.trim();
             
             if (!query) {
-                document.getElementById('map-search-results').innerHTML = '<p style="text-align: center; color: var(--text-secondary); padding: 20px;">Type to search for local tracks...</p>';
+                document.getElementById('map-search-results').innerHTML = '<p style="text-align: center; color: var(--text-secondary); padding: 20px;">Type to search for local tracks or paste a Jellyfin URL...</p>';
                 return;
             }
             
+            // Clear URL input when searching
+            document.getElementById('map-jellyfin-url').value = '';
+            
             // Debounce search
             clearTimeout(searchTimeout);
             searchTimeout = setTimeout(async () => {
@@ -1792,6 +1806,77 @@
             }, 300);
         }
         
+        async function extractJellyfinId() {
+            const url = document.getElementById('map-jellyfin-url').value.trim();
+            
+            if (!url) {
+                document.getElementById('map-search-results').innerHTML = '<p style="text-align: center; color: var(--text-secondary); padding: 20px;">Type to search for local tracks or paste a Jellyfin URL...</p>';
+                document.getElementById('map-selected-jellyfin-id').value = '';
+                document.getElementById('map-save-btn').disabled = true;
+                return;
+            }
+            
+            // Clear search input when using URL
+            document.getElementById('map-search-query').value = '';
+            
+            // Extract ID from URL patterns:
+            // https://jellyfin.example.com/web/#/details?id=XXXXX&serverId=...
+            // https://jellyfin.example.com/web/index.html#!/details?id=XXXXX
+            let jellyfinId = null;
+            
+            try {
+                const idMatch = url.match(/[?&]id=([a-f0-9]+)/i);
+                if (idMatch) {
+                    jellyfinId = idMatch[1];
+                }
+            } catch (e) {
+                // Invalid URL format
+            }
+            
+            if (!jellyfinId) {
+                document.getElementById('map-search-results').innerHTML = '<p style="text-align: center; color: var(--error); padding: 20px;">Could not extract track ID from URL. Make sure it contains "?id=..."</p>';
+                document.getElementById('map-selected-jellyfin-id').value = '';
+                document.getElementById('map-save-btn').disabled = true;
+                return;
+            }
+            
+            // Fetch track details to show preview
+            document.getElementById('map-search-results').innerHTML = '<div class="loading"><span class="spinner"></span> Loading track details...</div>';
+            
+            try {
+                const res = await fetch('/api/admin/jellyfin/track/' + jellyfinId);
+                const track = await res.json();
+                
+                if (res.ok && track.id) {
+                    document.getElementById('map-selected-jellyfin-id').value = track.id;
+                    document.getElementById('map-save-btn').disabled = false;
+                    
+                    document.getElementById('map-search-results').innerHTML = `
+                        <div class="track-item" style="border: 2px solid var(--accent); background: var(--bg-tertiary);">
+                            <div class="track-info">
+                                <h4>${escapeHtml(track.title)}</h4>
+                                <span class="artists">${escapeHtml(track.artist)}</span>
+                            </div>
+                            <div class="track-meta">
+                                ${track.album ? escapeHtml(track.album) : ''}
+                            </div>
+                        </div>
+                        <p style="text-align: center; color: var(--success); padding: 12px; margin-top: 8px;">
+                            ✓ Track loaded from URL. Click "Save Mapping" to confirm.
+                        </p>
+                    `;
+                } else {
+                    document.getElementById('map-search-results').innerHTML = '<p style="text-align: center; color: var(--error); padding: 20px;">Track not found in Jellyfin</p>';
+                    document.getElementById('map-selected-jellyfin-id').value = '';
+                    document.getElementById('map-save-btn').disabled = true;
+                }
+            } catch (error) {
+                document.getElementById('map-search-results').innerHTML = '<p style="text-align: center; color: var(--error); padding: 20px;">Failed to load track details</p>';
+                document.getElementById('map-selected-jellyfin-id').value = '';
+                document.getElementById('map-save-btn').disabled = true;
+            }
+        }
+        
         function selectJellyfinTrack(jellyfinId, element) {
             // Remove selection from all tracks
             document.querySelectorAll('#map-search-results .track-item').forEach(el => {