diff --git a/MoneyMap/Services/ReceiptManager.cs b/MoneyMap/Services/ReceiptManager.cs
index 5033cd2..410aef1 100644
--- a/MoneyMap/Services/ReceiptManager.cs
+++ b/MoneyMap/Services/ReceiptManager.cs
@@ -23,15 +23,37 @@ namespace MoneyMap.Services
         private readonly IWebHostEnvironment _environment;
         private readonly IConfiguration _configuration;
         private readonly IServiceProvider _serviceProvider;
+        private readonly ILogger<ReceiptManager> _logger;
         private const long MaxFileSize = 10 * 1024 * 1024; // 10MB
         private static readonly string[] AllowedExtensions = { ".jpg", ".jpeg", ".png", ".pdf", ".gif", ".heic" };
 
-        public ReceiptManager(MoneyMapContext db, IWebHostEnvironment environment, IConfiguration configuration, IServiceProvider serviceProvider)
+        // Magic bytes for file type validation (prevents extension spoofing)
+        private static readonly Dictionary<string, byte[][]> FileSignatures = new()
+        {
+            { ".jpg", new[] { new byte[] { 0xFF, 0xD8, 0xFF } } },
+            { ".jpeg", new[] { new byte[] { 0xFF, 0xD8, 0xFF } } },
+            { ".png", new[] { new byte[] { 0x89, 0x50, 0x4E, 0x47, 0x0D, 0x0A, 0x1A, 0x0A } } },
+            { ".gif", new[] { new byte[] { 0x47, 0x49, 0x46, 0x38 } } }, // GIF87a or GIF89a
+            { ".pdf", new[] { new byte[] { 0x25, 0x50, 0x44, 0x46 } } }, // %PDF
+            { ".heic", new[] {
+                new byte[] { 0x00, 0x00, 0x00, 0x18, 0x66, 0x74, 0x79, 0x70, 0x68, 0x65, 0x69, 0x63 }, // ftypheic
+                new byte[] { 0x00, 0x00, 0x00, 0x1C, 0x66, 0x74, 0x79, 0x70, 0x68, 0x65, 0x69, 0x63 }, // ftypheic (variant)
+                new byte[] { 0x00, 0x00, 0x00 } // Generic ftyp header (relaxed check)
+            }}
+        };
+
+        public ReceiptManager(
+            MoneyMapContext db,
+            IWebHostEnvironment environment,
+            IConfiguration configuration,
+            IServiceProvider serviceProvider,
+            ILogger<ReceiptManager> logger)
         {
             _db = db;
             _environment = environment;
             _configuration = configuration;
             _serviceProvider = serviceProvider;
+            _logger = logger;
         }
 
         private string GetReceiptsBasePath()
@@ -69,6 +91,10 @@ namespace MoneyMap.Services
             if (!AllowedExtensions.Contains(extension))
                 return ReceiptUploadResult.Failure($"File type {extension} not allowed. Use: {string.Join(", ", AllowedExtensions)}");
 
+            // Validate file content matches extension (magic bytes check)
+            if (!await ValidateFileSignatureAsync(file, extension))
+                return ReceiptUploadResult.Failure($"File content does not match {extension} format. The file may be corrupted or have an incorrect extension.");
+
             // Create receipts directory if it doesn't exist
             var receiptsBasePath = GetReceiptsBasePath();
             if (!Directory.Exists(receiptsBasePath))
@@ -133,10 +159,11 @@ namespace MoneyMap.Services
                     using var scope = _serviceProvider.CreateScope();
                     var parser = scope.ServiceProvider.GetRequiredService<IReceiptParser>();
                     await parser.ParseReceiptAsync(receipt.Id);
+                    _logger.LogInformation("Background parsing completed for receipt {ReceiptId}", receipt.Id);
                 }
-                catch
+                catch (Exception ex)
                 {
-                    // Silently fail - upload was successful, parsing is optional
+                    _logger.LogError(ex, "Background parsing failed for receipt {ReceiptId}: {Message}", receipt.Id, ex.Message);
                 }
             });
 
@@ -224,6 +251,23 @@ namespace MoneyMap.Services
             return true;
         }
 
+        private static async Task<bool> ValidateFileSignatureAsync(IFormFile file, string extension)
+        {
+            if (!FileSignatures.TryGetValue(extension, out var signatures))
+                return true; // No signature check for unknown extensions
+
+            var maxSignatureLength = signatures.Max(s => s.Length);
+            var headerBytes = new byte[Math.Min(maxSignatureLength, (int)file.Length)];
+
+            await using var stream = file.OpenReadStream();
+            _ = await stream.ReadAsync(headerBytes.AsMemory(0, headerBytes.Length));
+
+            // Check if file starts with any of the valid signatures for this extension
+            return signatures.Any(signature =>
+                headerBytes.Length >= signature.Length &&
+                headerBytes.Take(signature.Length).SequenceEqual(signature));
+        }
+
         private static string SanitizeFileName(string fileName)
         {
             if (string.IsNullOrWhiteSpace(fileName))