diff --git a/SatelliteProvider.IntegrationTests/ExtendedRouteTests.cs b/SatelliteProvider.IntegrationTests/ExtendedRouteTests.cs
index a53efa8..b3eeeaa 100644
--- a/SatelliteProvider.IntegrationTests/ExtendedRouteTests.cs
+++ b/SatelliteProvider.IntegrationTests/ExtendedRouteTests.cs
@@ -160,12 +160,35 @@ public static class ExtendedRouteTests
             }
 
             var firstEntry = zipArchive.Entries[0];
-            Console.WriteLine($"  First entry: {firstEntry.Name} ({firstEntry.Length} bytes)");
+            Console.WriteLine($"  First entry: {firstEntry.FullName} ({firstEntry.Length} bytes)");
             
             if (firstEntry.Length == 0)
             {
                 throw new Exception("First entry in ZIP is empty");
             }
+
+            var entriesWithDirs = zipArchive.Entries.Where(e => e.FullName.Contains('/')).ToList();
+            Console.WriteLine($"  Entries with directory structure: {entriesWithDirs.Count}/{zipArchive.Entries.Count}");
+            
+            if (entriesWithDirs.Count == 0)
+            {
+                throw new Exception("ZIP should preserve directory structure but found no entries with paths");
+            }
+
+            var samplePaths = entriesWithDirs.Take(3).Select(e => e.FullName).ToList();
+            Console.WriteLine($"  Sample paths:");
+            foreach (var path in samplePaths)
+            {
+                Console.WriteLine($"    - {path}");
+            }
+
+            var pathParts = firstEntry.FullName.Split('/');
+            if (pathParts.Length < 4)
+            {
+                throw new Exception($"Expected directory structure like '18/158/91/tile_xxx.jpg' but got '{firstEntry.FullName}'");
+            }
+
+            Console.WriteLine($"  ✓ Directory structure preserved (zoom/{pathParts[0]}/x-bucket/{pathParts[1]}/y-bucket/{pathParts[2]}/file)");
         }
 
         Console.WriteLine();
diff --git a/SatelliteProvider.Services/RouteProcessingService.cs b/SatelliteProvider.Services/RouteProcessingService.cs
index fe2dff9..ef53f87 100644
--- a/SatelliteProvider.Services/RouteProcessingService.cs
+++ b/SatelliteProvider.Services/RouteProcessingService.cs
@@ -701,6 +701,9 @@ public class RouteProcessingService : BackgroundService
             int addedFiles = 0;
             int missingFiles = 0;
 
+            var tilesBasePath = _storageConfig.TilesDirectory;
+            var normalizedBasePath = Path.GetFullPath(tilesBasePath).TrimEnd(Path.DirectorySeparatorChar, Path.AltDirectorySeparatorChar);
+
             foreach (var tile in tiles)
             {
                 if (cancellationToken.IsCancellationRequested)
@@ -710,8 +713,20 @@ public class RouteProcessingService : BackgroundService
                 {
                     try
                     {
-                        var fileName = Path.GetFileName(tile.FilePath);
-                        zipArchive.CreateEntryFromFile(tile.FilePath, fileName, CompressionLevel.Optimal);
+                        var fullPath = Path.GetFullPath(tile.FilePath);
+                        string entryName;
+
+                        if (fullPath.StartsWith(normalizedBasePath, StringComparison.OrdinalIgnoreCase))
+                        {
+                            entryName = fullPath.Substring(normalizedBasePath.Length + 1);
+                            entryName = entryName.Replace(Path.DirectorySeparatorChar, '/');
+                        }
+                        else
+                        {
+                            entryName = Path.GetFileName(tile.FilePath);
+                        }
+
+                        zipArchive.CreateEntryFromFile(tile.FilePath, entryName, CompressionLevel.Optimal);
                         addedFiles++;
                     }
                     catch (Exception ex)