diff --git a/app/admin/page.tsx b/app/admin/page.tsx
index 9d7351e..126fa1a 100644
--- a/app/admin/page.tsx
+++ b/app/admin/page.tsx
@@ -462,6 +462,16 @@ export default function AdminPage() {
                         song: data.song,
                         validation: data.validation
                     });
+                } else if (res.status === 409) {
+                    // Duplicate detected
+                    const data = await res.json();
+                    results.push({
+                        filename: file.name,
+                        success: false,
+                        isDuplicate: true,
+                        duplicate: data.duplicate,
+                        error: `Duplicate: Already exists as "${data.duplicate.title}" by "${data.duplicate.artist}"`
+                    });
                 } else {
                     results.push({
                         filename: file.name,
@@ -486,12 +496,24 @@ export default function AdminPage() {
 
         // Auto-trigger categorization after uploads
         const successCount = results.filter(r => r.success).length;
+        const duplicateCount = results.filter(r => r.isDuplicate).length;
+        const failedCount = results.filter(r => !r.success && !r.isDuplicate).length;
         if (successCount > 0) {
-            setMessage(`✅ Uploaded ${successCount}/${files.length} songs successfully!\n\n🤖 Starting auto-categorization...`);
+            let msg = `✅ Uploaded ${successCount}/${files.length} songs successfully!`;
+            if (duplicateCount > 0) {
+                msg += `\n⚠️ Skipped ${duplicateCount} duplicate(s)`;
+            }
+            if (failedCount > 0) {
+                msg += `\n❌ ${failedCount} failed`;
+            }
+            msg += '\n\n🤖 Starting auto-categorization...';
+            setMessage(msg);
             // Small delay to let user see the message
             setTimeout(() => {
                 handleAICategorization();
             }, 1000);
+        } else if (duplicateCount > 0 && failedCount === 0) {
+            setMessage(`⚠️ All ${duplicateCount} file(s) were duplicates - nothing uploaded.`);
         } else {
             setMessage(`❌ All uploads failed.`);
         }
diff --git a/app/api/songs/route.ts b/app/api/songs/route.ts
index ce62ae7..2e21076 100644
--- a/app/api/songs/route.ts
+++ b/app/api/songs/route.ts
@@ -3,6 +3,7 @@ import { PrismaClient } from '@prisma/client';
 import { writeFile, unlink } from 'fs/promises';
 import path from 'path';
 import { parseBuffer } from 'music-metadata';
+import { isDuplicateSong } from '@/lib/fuzzyMatch';
 
 const prisma = new PrismaClient();
 
@@ -72,8 +73,16 @@ export async function POST(request: Request) {
             if (metadata.common.title) {
                 title = metadata.common.title;
             }
-            if (metadata.common.artist) {
+
+            // Handle artist - prefer artists array if available
+            if (metadata.common.artists && metadata.common.artists.length > 0) {
+                // Join multiple artists with '/'
+                artist = metadata.common.artists.join('/');
+            } else if (metadata.common.artist) {
                 artist = metadata.common.artist;
+            } else if (metadata.common.albumartist) {
+                // Fallback to album artist
+                artist = metadata.common.albumartist;
             }
 
             // Validation info
@@ -114,6 +123,28 @@ export async function POST(request: Request) {
         if (!title) title = 'Unknown Title';
         if (!artist) artist = 'Unknown Artist';
 
+        // Check for duplicates
+        const existingSongs = await prisma.song.findMany({
+            select: { id: true, title: true, artist: true, filename: true }
+        });
+
+        for (const existing of existingSongs) {
+            if (isDuplicateSong(artist, title, existing.artist, existing.title)) {
+                return NextResponse.json(
+                    {
+                        error: 'Duplicate song detected',
+                        duplicate: {
+                            id: existing.id,
+                            title: existing.title,
+                            artist: existing.artist,
+                            filename: existing.filename
+                        }
+                    },
+                    { status: 409 }
+                );
+            }
+        }
+
         // Create URL-safe filename
         const originalName = file.name.replace(/\.mp3$/i, '');
         const sanitizedName = originalName
diff --git a/lib/fuzzyMatch.ts b/lib/fuzzyMatch.ts
new file mode 100644
index 0000000..55f451f
--- /dev/null
+++ b/lib/fuzzyMatch.ts
@@ -0,0 +1,97 @@
+/**
+ * Fuzzy string matching utility for duplicate detection
+ * Uses Levenshtein distance to compare strings with tolerance for formatting variations
+ */
+
+/**
+ * Normalize a string for comparison
+ * - Converts to lowercase
+ * - Removes special characters
+ * - Normalizes whitespace
+ */
+function normalizeString(str: string): string {
+    return str
+        .toLowerCase()
+        .replace(/[^a-z0-9\s]/g, '') // Remove special chars
+        .replace(/\s+/g, ' ')         // Normalize whitespace
+        .trim();
+}
+
+/**
+ * Calculate Levenshtein distance between two strings
+ * Returns the minimum number of single-character edits needed to change one string into the other
+ */
+function levenshteinDistance(a: string, b: string): number {
+    if (a.length === 0) return b.length;
+    if (b.length === 0) return a.length;
+
+    const matrix: number[][] = [];
+
+    // Initialize first column
+    for (let i = 0; i <= b.length; i++) {
+        matrix[i] = [i];
+    }
+
+    // Initialize first row
+    for (let j = 0; j <= a.length; j++) {
+        matrix[0][j] = j;
+    }
+
+    // Fill in the rest of the matrix
+    for (let i = 1; i <= b.length; i++) {
+        for (let j = 1; j <= a.length; j++) {
+            if (b.charAt(i - 1) === a.charAt(j - 1)) {
+                matrix[i][j] = matrix[i - 1][j - 1];
+            } else {
+                matrix[i][j] = Math.min(
+                    matrix[i - 1][j - 1] + 1, // substitution
+                    matrix[i][j - 1] + 1,     // insertion
+                    matrix[i - 1][j] + 1      // deletion
+                );
+            }
+        }
+    }
+
+    return matrix[b.length][a.length];
+}
+
+/**
+ * Check if two strings are similar based on Levenshtein distance
+ * @param str1 First string to compare
+ * @param str2 Second string to compare
+ * @param threshold Similarity threshold (0-1), default 0.85
+ * @returns true if strings are similar enough
+ */
+export function isSimilar(str1: string, str2: string, threshold = 0.85): boolean {
+    if (!str1 || !str2) return false;
+
+    const norm1 = normalizeString(str1);
+    const norm2 = normalizeString(str2);
+
+    // Exact match after normalization
+    if (norm1 === norm2) return true;
+
+    const distance = levenshteinDistance(norm1, norm2);
+    const maxLen = Math.max(norm1.length, norm2.length);
+
+    // Avoid division by zero
+    if (maxLen === 0) return true;
+
+    const similarity = 1 - (distance / maxLen);
+
+    return similarity >= threshold;
+}
+
+/**
+ * Check if a song (artist + title) is a duplicate of another
+ * Both artist AND title must be similar for a match
+ */
+export function isDuplicateSong(
+    artist1: string,
+    title1: string,
+    artist2: string,
+    title2: string,
+    threshold = 0.85
+): boolean {
+    return isSimilar(artist1, artist2, threshold) && isSimilar(title1, title2, threshold);
+}