diff --git a/pom.xml b/pom.xml
index ed7118c..f29e8e7 100644
--- a/pom.xml
+++ b/pom.xml
@@ -124,6 +124,12 @@
 			<version>3.2.3</version>
 			<scope>compile</scope>
 		</dependency>
+		<dependency>
+			<groupId>net.grey-panther</groupId>
+			<artifactId>natural-comparator</artifactId>
+			<version>1.1</version>
+			<scope>compile</scope>
+		</dependency>
 	</dependencies>
 
 	<build>
diff --git a/src/main/java/com/magamochi/content/service/ContentImportService.java b/src/main/java/com/magamochi/content/service/ContentImportService.java
index 0877bb0..9adafef 100644
--- a/src/main/java/com/magamochi/content/service/ContentImportService.java
+++ b/src/main/java/com/magamochi/content/service/ContentImportService.java
@@ -18,13 +18,12 @@ import com.magamochi.ingestion.service.ContentProviderService;
 import jakarta.validation.constraints.NotNull;
 import java.io.ByteArrayOutputStream;
 import java.io.IOException;
-import java.util.Comparator;
-import java.util.List;
-import java.util.Set;
+import java.util.*;
 import java.util.zip.ZipEntry;
 import java.util.zip.ZipInputStream;
 import lombok.RequiredArgsConstructor;
 import lombok.extern.log4j.Log4j2;
+import net.greypanther.natsort.CaseInsensitiveSimpleNaturalComparator;
 import org.springframework.stereotype.Service;
 import org.springframework.transaction.annotation.Transactional;
 import org.springframework.web.multipart.MultipartFile;
@@ -90,21 +89,27 @@ public class ContentImportService {
             null,
             "en-US");
 
-    try {
-      var is = s3Service.getFileStream(filename);
-      var zis = new ZipInputStream(is);
+    try (var is = s3Service.getFileStream(filename);
+        var zis = new ZipInputStream(is)) {
+
+      Map<String, byte[]> entryMap =
+          new TreeMap<>(
+              CaseInsensitiveSimpleNaturalComparator
+                  .getInstance()); // TreeMap keeps keys sorted naturally
 
       ZipEntry entry;
-      var position = 0;
-
       while ((entry = zis.getNextEntry()) != null) {
-        if (entry.isDirectory()) {
-          continue;
-        }
+        if (entry.isDirectory()) continue;
 
-        var os = new ByteArrayOutputStream();
+        ByteArrayOutputStream os = new ByteArrayOutputStream();
         zis.transferTo(os);
-        var bytes = os.toByteArray();
+        entryMap.put(entry.getName(), os.toByteArray());
+        zis.closeEntry();
+      }
+
+      int position = 0;
+      for (Map.Entry<String, byte[]> sortedEntry : entryMap.entrySet()) {
+        byte[] bytes = sortedEntry.getValue();
 
         var imageId = imageFetchService.uploadImage(bytes, null, ContentType.CONTENT_IMAGE);
         var image = imageService.find(imageId);
@@ -113,13 +118,11 @@ public class ContentImportService {
             MangaContentImage.builder()
                 .image(image)
                 .mangaContent(mangaContent)
-                .position(position)
+                .position(position++)
                 .build());
-
-        zis.closeEntry();
       }
     } catch (Exception e) {
-      throw new RuntimeException(e);
+      throw new RuntimeException("Failed to process zip: " + filename, e);
     }
 
     mangaContent.setDownloaded(true);