diff --git a/packages/core/lib/plugins/segment_destination.dart b/packages/core/lib/plugins/segment_destination.dart
index 501d213..e211ba1 100644
--- a/packages/core/lib/plugins/segment_destination.dart
+++ b/packages/core/lib/plugins/segment_destination.dart
@@ -30,22 +30,31 @@ class SegmentDestination extends DestinationPlugin with Flushable {
     final List<RawEvent> sentEvents = [];
     var numFailedEvents = 0;
 
+    // FIXED: Only dequeue successfully sent events 
     await Future.forEach(chunkedEvents, (batch) async {
       try {
         final succeeded = await analytics?.httpClient.startBatchUpload(
             analytics!.state.configuration.state.writeKey, batch,
             host: _apiHost);
-        if (succeeded == null || !succeeded) {
+
+        if (succeeded == true) {
+          // Only add to sentEvents on actual success
+          sentEvents.addAll(batch);
+        } else {
           numFailedEvents += batch.length;
         }
-        sentEvents.addAll(batch);
       } catch (e) {
         numFailedEvents += batch.length;
-      } finally {
-        _queuePlugin.dequeue(sentEvents);
+        // Don't add failed events to sentEvents
       }
+      // Move dequeue outside finally, after the loop
     });
 
+    // Only dequeue events that were actually sent successfully
+    if (sentEvents.isNotEmpty) {
+      _queuePlugin.dequeue(sentEvents);
+    }
+
     if (sentEvents.isNotEmpty) {
       log("Sent ${sentEvents.length} events", kind: LogFilterKind.debug);
     }
diff --git a/packages/core/lib/utils/store/io.dart b/packages/core/lib/utils/store/io.dart
index f93b53d..91810f4 100644
--- a/packages/core/lib/utils/store/io.dart
+++ b/packages/core/lib/utils/store/io.dart
@@ -10,19 +10,28 @@ import 'package:path_provider/path_provider.dart';
 
 class StoreImpl with Store {
   final bool storageJson;
-  StoreImpl({this.storageJson = true});
+  late final Future<void> _migrationCompleted;
+  
+  StoreImpl({this.storageJson = true}) {
+    // Start migration immediately but don't block construction
+    _migrationCompleted = _migrateFilesFromDocumentsToSupport();
+  }
+  @override
+  Future get ready => Future.value();
+
   @override
-  Future<Map<String, dynamic>?> getPersisted(String key) {
+  Future<Map<String, dynamic>?> getPersisted(String key) async {
     if (!storageJson) return Future.value(null);
+    // Ensure migration is complete before reading files
+    await _migrationCompleted;
     return _readFile(key);
   }
 
   @override
-  Future get ready => Future.value();
-
-  @override
-  Future setPersisted(String key, Map<String, dynamic> value) {
+  Future setPersisted(String key, Map<String, dynamic> value) async {
     if (!storageJson) return Future.value();
+    // Ensure migration is complete before writing files
+    await _migrationCompleted;
     return _writeFile(key, value);
   }
   
@@ -70,7 +79,7 @@ class StoreImpl with Store {
   }
 
   Future<String> _fileName(String fileKey) async {
-    final path = (await _getDocumentDir()).path;
+    final path = (await _getNewDocumentDir()).path;
     return "$path/analytics-flutter-$fileKey.json";
   }
 
@@ -88,7 +97,15 @@ class StoreImpl with Store {
     }
   }
 
-  Future<Directory> _getDocumentDir() async {
+  Future<Directory> _getNewDocumentDir() async {
+    try {
+      return await getApplicationSupportDirectory();
+    } catch (err) {
+      throw PlatformNotSupportedError();
+    }
+  }
+
+  Future<Directory> _getOldDocumentDir() async {
     try {
       return await getApplicationDocumentsDirectory();
     } catch (err) {
@@ -96,6 +113,44 @@ class StoreImpl with Store {
     }
   }
 
+  /// Migrates existing analytics files from Documents directory to Application Support directory
+  Future<void> _migrateFilesFromDocumentsToSupport() async {
+    try {
+      final oldDir = await _getOldDocumentDir();
+      final newDir = await _getNewDocumentDir();
+      
+      // List all analytics files in the old directory
+      final oldDirFiles = oldDir.listSync()
+          .whereType<File>()
+          .where((file) => file.path.contains('analytics-flutter-') && file.path.endsWith('.json'))
+          .toList();
+      
+      for (final oldFile in oldDirFiles) {
+        final fileName = oldFile.path.split('/').last;
+        final newFilePath = '${newDir.path}/$fileName';
+        final newFile = File(newFilePath);
+        
+        // Only migrate if the file doesn't already exist in the new location
+        if (!await newFile.exists()) {
+          try {
+            // Ensure the new directory exists
+            await newDir.create(recursive: true);
+            
+            // Copy the file to the new location
+            await oldFile.copy(newFilePath);
+            
+            // Delete the old file after successful copy
+            await oldFile.delete();
+          } catch (e) {
+            // The app should continue to work even if migration fails
+          }
+        }
+      }
+    } catch (e) {
+      // Migration failure shouldn't break the app
+    }
+  }
+
   @override
   void dispose() {}
 }