diff --git a/lib/config/routes.dart b/lib/config/routes.dart
index 7f761a87e6..864858c132 100644
--- a/lib/config/routes.dart
+++ b/lib/config/routes.dart
@@ -1,3 +1,4 @@
+import 'package:fluffychat/di/send_image/send_image_di.dart';
 import 'package:fluffychat/pages/add_story/add_story.dart';
 import 'package:fluffychat/pages/archive/archive.dart';
 import 'package:fluffychat/pages/chat/chat.dart';
@@ -101,8 +102,9 @@ class AppRoutes {
                 stackedRoutes: _chatDetailsRoutes,
                 buildTransition: _rightToLeftTransition,
               ),
-              VWidget(
+              VWidgetWithDependency(
                 path: '/rooms/:roomid',
+                di: SendImageDi(),
                 widget: const Chat(),
                 buildTransition: _rightToLeftTransition,
                 stackedRoutes: [
diff --git a/lib/di/send_image/send_image_di.dart b/lib/di/send_image/send_image_di.dart
new file mode 100644
index 0000000000..e9673b4a2c
--- /dev/null
+++ b/lib/di/send_image/send_image_di.dart
@@ -0,0 +1,13 @@
+import 'package:fluffychat/di/base_di.dart';
+import 'package:fluffychat/domain/usecase/send_image_interactor.dart';
+import 'package:get_it/get_it.dart';
+
+class SendImageDi extends BaseDI {
+  @override
+  String get scopeName => "Send image";
+
+  @override
+  void setUp(GetIt get) {
+    get.registerSingleton<SendImageInteractor>(SendImageInteractor());
+  }
+}
\ No newline at end of file
diff --git a/lib/domain/usecase/send_image_interactor.dart b/lib/domain/usecase/send_image_interactor.dart
new file mode 100644
index 0000000000..defc206f79
--- /dev/null
+++ b/lib/domain/usecase/send_image_interactor.dart
@@ -0,0 +1,33 @@
+
+import 'package:fluffychat/presentation/extensions/room_extension.dart';
+import 'package:matrix/matrix.dart';
+import 'package:photo_manager/photo_manager.dart';
+import 'package:fluffychat/presentation/extensions/asset_entity_extension.dart';
+
+class SendImageInteractor {
+  Future<void> execute({
+    required Room room,
+    required AssetEntity entity,
+    String? txId,
+    Event? inReplyTo,
+    String? editEventId,
+    int? shrinkImageMaxDimension,
+    Map<String, dynamic>? extraContent,
+  }) async {
+    final matrixFile = await entity.toMatrixFile();
+    if (matrixFile != null) {
+      try {
+        final mxcUri = await room.sendImageFileEvent(
+          matrixFile,
+          txid: txId,
+          editEventId: editEventId,
+          inReplyTo: inReplyTo,
+          shrinkImageMaxDimension: shrinkImageMaxDimension,
+          extraContent: extraContent,
+        );
+      } catch(error) {
+        Logs().d("SendImageInteractor: execute(): $error");
+      }
+    }
+  }
+}
\ No newline at end of file
diff --git a/lib/pages/chat/chat.dart b/lib/pages/chat/chat.dart
index 9aa28f7db1..927da35697 100644
--- a/lib/pages/chat/chat.dart
+++ b/lib/pages/chat/chat.dart
@@ -2,9 +2,9 @@ import 'dart:async';
 import 'dart:io';
 
 import 'package:fluffychat/di/global/get_it_initializer.dart';
+import 'package:fluffychat/domain/usecase/send_image_interactor.dart';
 import 'package:fluffychat/pages/forward/forward.dart';
 import 'package:fluffychat/utils/network_connection_service.dart';
-import 'package:fluffychat/presentation/extensions/asset_entity_extension.dart';
 import 'package:fluffychat/utils/voip/permission_service.dart';
 import 'package:flutter/material.dart';
 import 'package:flutter/scheduler.dart';
@@ -16,16 +16,17 @@ import 'package:device_info_plus/device_info_plus.dart';
 import 'package:emoji_picker_flutter/emoji_picker_flutter.dart';
 import 'package:file_picker_cross/file_picker_cross.dart';
 import 'package:flutter_gen/gen_l10n/l10n.dart';
-import 'package:fluttertoast/fluttertoast.dart';
 import 'package:future_loading_dialog/future_loading_dialog.dart';
 import 'package:image_picker/image_picker.dart';
 import 'package:linagora_design_flutter/images_picker/images_picker.dart' hide ImagePicker;
 import 'package:matrix/matrix.dart';
 import 'package:permission_handler/permission_handler.dart';
+import 'package:photo_manager/photo_manager.dart';
 import 'package:record/record.dart';
 import 'package:scroll_to_index/scroll_to_index.dart';
 import 'package:shared_preferences/shared_preferences.dart';
 import 'package:vrouter/vrouter.dart';
+import 'package:fluffychat/presentation/extensions/room_extension.dart';
 
 import 'package:fluffychat/pages/chat/chat_view.dart';
 import 'package:fluffychat/pages/chat/event_info_dialog.dart';
@@ -397,28 +398,25 @@ class ChatController extends State<Chat> {
     );
   }
 
-  Future<void> sendImage(IndexedAssetEntity entity) async {
-    final matrixFile = await entity.toMatrixFile();
-    if (matrixFile != null) {
-      await room!.sendFileEvent(
-        matrixFile,
-        thumbnail: null,
-      ).catchError((e) {
-        Fluttertoast.showToast(
-          msg: "error: $e",
-          gravity: ToastGravity.BOTTOM,
-        );
-        return null;
-      });
+  void sendImage() {
+    final assetEntity = imagePickerController.selectedAssets.first;
+    final sendImageInteractor = getIt.get<SendImageInteractor>();
+    if (assetEntity.asset.type == AssetType.image) {
+      sendImageInteractor.execute(room: room!, entity: assetEntity.asset);
+      imagePickerController.clearAssetCounter();
+      numberSelectedImagesNotifier.value = 0;
     }
   }
 
-  Future<void> sendImages() async {
-    final selectedAssets = imagePickerController.sortedSelectedAssets;
-    for (final entity in selectedAssets) {
-      await sendImage(entity);
-    }
-  }
+  // Future<void> sendImages() async {
+  //   final selectedAssets = imagePickerController.sortedSelectedAssets;
+  //   for (final entity in selectedAssets) {
+  //     await sendImage();
+  //   }
+
+  //   imagePickerController.clearAssetCounter();
+  //   numberSelectedImagesNotifier.value = 0;
+  // }
 
   void openCameraAction() async {
     // Make sure the textfield is unfocused before opening the camera
diff --git a/lib/pages/chat/chat_input_row.dart b/lib/pages/chat/chat_input_row.dart
index d884e60335..548ac7e75f 100644
--- a/lib/pages/chat/chat_input_row.dart
+++ b/lib/pages/chat/chat_input_row.dart
@@ -340,7 +340,7 @@ Future<void> showImagesPickerBottomSheet({
                         InkWell(
                           borderRadius: const BorderRadius.all(Radius.circular(100)),
                           onTap: () {
-                            controller.sendImages();
+                            controller.sendImage();
                             Navigator.of(context).pop();
                           },
                           child: SvgPicture.asset(
diff --git a/lib/pages/chat/events/message_content.dart b/lib/pages/chat/events/message_content.dart
index 0120fb0720..fb8d5f75a0 100644
--- a/lib/pages/chat/events/message_content.dart
+++ b/lib/pages/chat/events/message_content.dart
@@ -1,4 +1,5 @@
 import 'package:fluffychat/pages/chat/events/message_content_style.dart';
+import 'package:fluffychat/pages/chat/events/sending_image_widget.dart';
 import 'package:fluffychat/widgets/twake_link_text.dart';
 import 'package:flutter/material.dart';
 
@@ -9,6 +10,7 @@ import 'package:fluffychat/pages/chat/events/video_player.dart';
 import 'package:fluffychat/utils/adaptive_bottom_sheet.dart';
 import 'package:fluffychat/utils/date_time_extension.dart';
 import 'package:fluffychat/utils/matrix_sdk_extensions/matrix_locals.dart';
+import 'package:fluffychat/utils/matrix_sdk_extensions/event_extension.dart';
 import 'package:fluffychat/widgets/avatar/avatar.dart';
 import 'package:fluffychat/widgets/matrix.dart';
 import '../../../config/app_config.dart';
@@ -112,6 +114,20 @@ class MessageContent extends StatelessWidget {
       case EventTypes.Sticker:
         switch (event.messageType) {
           case MessageTypes.Image:
+            if (event.status == EventStatus.error && event.messageType == MessageTypes.Image) {
+              return SizedBox(
+                width: MessageContentStyle.imageBubbleWidth,
+                height: MessageContentStyle.imageBubbleHeight,
+                child: const Center(
+                  child: Icon(Icons.error, color: Colors.red),
+                ),
+              );
+            }
+
+            final sendingImageData = event.getSendingImageData();
+            if (sendingImageData != null) {
+              return SendingImageWidget(sendingImageData: sendingImageData);
+            }
             return ImageBubble(
               event,
               width: MessageContentStyle.imageBubbleWidth,
diff --git a/lib/pages/chat/events/sending_image_widget.dart b/lib/pages/chat/events/sending_image_widget.dart
new file mode 100644
index 0000000000..db14a66941
--- /dev/null
+++ b/lib/pages/chat/events/sending_image_widget.dart
@@ -0,0 +1,27 @@
+import 'dart:typed_data';
+
+import 'package:fluffychat/pages/chat/events/message_content_style.dart';
+import 'package:flutter/material.dart';
+
+class SendingImageWidget extends StatelessWidget {
+  const SendingImageWidget({
+    super.key,
+    required this.sendingImageData,
+  });
+
+  final Uint8List sendingImageData;
+
+  @override
+  Widget build(BuildContext context) {
+    return ClipRRect(
+      borderRadius: BorderRadius.circular(12.0),
+      child: Image.memory(
+        sendingImageData,
+        width: MessageContentStyle.imageBubbleWidth,
+        height: MessageContentStyle.imageBubbleHeight,
+        fit: BoxFit.cover,
+        filterQuality: FilterQuality.medium,
+      ),
+    );
+  }
+}
\ No newline at end of file
diff --git a/lib/presentation/extensions/asset_entity_extension.dart b/lib/presentation/extensions/asset_entity_extension.dart
index 065810cb02..b64d840eb8 100644
--- a/lib/presentation/extensions/asset_entity_extension.dart
+++ b/lib/presentation/extensions/asset_entity_extension.dart
@@ -1,11 +1,11 @@
-import 'package:linagora_design_flutter/images_picker/images_picker.dart';
 import 'package:matrix/matrix.dart';
+import 'package:photo_manager/photo_manager.dart';
 
-extension AssetEntityExtension on IndexedAssetEntity {
+extension AssetEntityExtension on AssetEntity {
   Future<MatrixFile?> toMatrixFile() async {
-    final bytes = await asset.originBytes;
+    final bytes = await originBytes;
     if (bytes != null && bytes.isNotEmpty) {
-      return MatrixFile(bytes: bytes, name: await asset.titleAsync);
+      return MatrixFile(bytes: bytes, name: title ?? await titleAsync);
     }
     return null;
   }
diff --git a/lib/presentation/extensions/room_extension.dart b/lib/presentation/extensions/room_extension.dart
new file mode 100644
index 0000000000..cf3e0317a1
--- /dev/null
+++ b/lib/presentation/extensions/room_extension.dart
@@ -0,0 +1,216 @@
+import 'package:matrix/matrix.dart';
+import 'package:matrix/src/utils/file_send_request_credentials.dart';
+
+extension SendImage on Room {
+
+  static const maxSendingImage = 20;
+
+  Future<String?> sendImageFileEvent(
+    MatrixFile file, {
+    String? txid,
+    Event? inReplyTo,
+    String? editEventId,
+    int? shrinkImageMaxDimension,
+    Map<String, dynamic>? extraContent,
+  }) async {
+    if (sendingFileThumbnails.entries.length > maxSendingImage) {
+      sendingFileThumbnails.clear();
+    }
+    if (sendingFilePlaceholders.entries.length > maxSendingImage) {
+      sendingFilePlaceholders.clear();
+    }
+
+    txid ??= client.generateUniqueTransactionId();
+    sendingFilePlaceholders[txid] = file;
+    sendingFileThumbnails[txid] =  MatrixImageFile(bytes: file.bytes, name: file.name);
+
+    // Create a fake Event object as a placeholder for the uploading file:
+    final syncUpdate = SyncUpdate(
+      nextBatch: '',
+      rooms: RoomsUpdate(
+        join: {
+          id: JoinedRoomUpdate(
+            timeline: TimelineUpdate(
+              events: [
+                MatrixEvent(
+                  content: {
+                    'msgtype': file.msgType,
+                    'body': file.name,
+                    'filename': file.name,
+                  },
+                  type: EventTypes.Message,
+                  eventId: txid,
+                  senderId: client.userID!,
+                  originServerTs: DateTime.now(),
+                  unsigned: {
+                    messageSendingStatusKey: EventStatus.sending.intValue,
+                    'transaction_id': txid,
+                    ...FileSendRequestCredentials(
+                      inReplyTo: inReplyTo?.eventId,
+                      editEventId: editEventId,
+                      shrinkImageMaxDimension: shrinkImageMaxDimension,
+                      extraContent: extraContent,
+                    ).toJson(),
+                  },
+                ),
+              ],
+            ),
+          ),
+        },
+      ),
+    );
+    await handleImageFakeSync(syncUpdate);
+    // Check media config of the server before sending the file. Stop if the
+    // Media config is unreachable or the file is bigger than the given maxsize.
+    try {
+      final mediaConfig = await client.getConfig();
+      final maxMediaSize = mediaConfig.mUploadSize;
+      if (maxMediaSize != null && maxMediaSize < file.bytes.lengthInBytes) {
+        throw FileTooBigMatrixException(file.bytes.lengthInBytes, maxMediaSize);
+      }
+    } catch (e) {
+      Logs().d('Config error while sending file', e);
+      syncUpdate.rooms!.join!.values.first.timeline!.events!.first
+          .unsigned![messageSendingStatusKey] = EventStatus.error.intValue;
+      await handleImageFakeSync(syncUpdate);
+      rethrow;
+    }
+
+    MatrixFile uploadFile = file; // ignore: omit_local_variable_types
+    var thumbnail = sendingFileThumbnails[txid];
+    // computing the thumbnail in case we can
+    if (file is MatrixImageFile && shrinkImageMaxDimension != null) {
+      file = await MatrixImageFile.shrink(
+        bytes: file.bytes,
+        name: file.name,
+        maxDimension: shrinkImageMaxDimension,
+        customImageResizer: client.customImageResizer,
+        nativeImplementations: client.nativeImplementations,
+      );
+
+      if (thumbnail != null && file.size < thumbnail.size) {
+        thumbnail = null; // in this case, the thumbnail is not usefull
+      }
+    }
+
+    MatrixFile? uploadThumbnail = thumbnail; // ignore: omit_local_variable_types
+    EncryptedFile? encryptedFile;
+    EncryptedFile? encryptedThumbnail;
+    if (encrypted && client.fileEncryptionEnabled) {
+      syncUpdate.rooms!.join!.values.first.timeline!.events!.first
+          .unsigned![fileSendingStatusKey] = FileSendingStatus.encrypting.name;
+      await handleImageFakeSync(syncUpdate);
+      encryptedFile = await file.encrypt();
+      uploadFile = encryptedFile.toMatrixFile();
+
+      if (thumbnail != null) {
+        encryptedThumbnail = await thumbnail.encrypt();
+        uploadThumbnail = encryptedThumbnail.toMatrixFile();
+      }
+    }
+    Uri? uploadResp, thumbnailUploadResp;
+
+    final timeoutDate = DateTime.now();
+
+    syncUpdate.rooms!.join!.values.first.timeline!.events!.first
+        .unsigned![fileSendingStatusKey] = FileSendingStatus.uploading.name;
+    while (uploadResp == null ||
+        (uploadThumbnail != null && thumbnailUploadResp == null)) {
+      try {
+        uploadResp = await client.uploadContent(
+          uploadFile.bytes,
+          filename: uploadFile.name,
+          contentType: uploadFile.mimeType,
+        );
+        thumbnailUploadResp = uploadThumbnail != null
+            ? await client.uploadContent(
+                uploadThumbnail.bytes,
+                filename: uploadThumbnail.name,
+                contentType: uploadThumbnail.mimeType,
+              )
+            : null;
+      } on MatrixException catch (_) {
+        syncUpdate.rooms!.join!.values.first.timeline!.events!.first
+            .unsigned![messageSendingStatusKey] = EventStatus.error.intValue;
+        await handleImageFakeSync(syncUpdate);
+        rethrow;
+      } catch (_) {
+        if (DateTime.now().isAfter(timeoutDate)) {
+          syncUpdate.rooms!.join!.values.first.timeline!.events!.first
+              .unsigned![messageSendingStatusKey] = EventStatus.error.intValue;
+          await handleImageFakeSync(syncUpdate);
+          rethrow;
+        }
+        Logs().v('Send File into room failed. Try again...');
+        await Future.delayed(const Duration(seconds: 1));
+      }
+    }
+
+    // Send event
+    final content = <String, dynamic>{
+      'msgtype': file.msgType,
+      'body': file.name,
+      'filename': file.name,
+      if (encryptedFile == null) 'url': uploadResp.toString(),
+      if (encryptedFile != null)
+        'file': {
+          'url': uploadResp.toString(),
+          'mimetype': file.mimeType,
+          'v': 'v2',
+          'key': {
+            'alg': 'A256CTR',
+            'ext': true,
+            'k': encryptedFile.k,
+            'key_ops': ['encrypt', 'decrypt'],
+            'kty': 'oct'
+          },
+          'iv': encryptedFile.iv,
+          'hashes': {'sha256': encryptedFile.sha256}
+        },
+      'info': {
+        ...file.info,
+        if (thumbnail != null && encryptedThumbnail == null)
+          'thumbnail_url': thumbnailUploadResp.toString(),
+        if (thumbnail != null && encryptedThumbnail != null)
+          'thumbnail_file': {
+            'url': thumbnailUploadResp.toString(),
+            'mimetype': thumbnail.mimeType,
+            'v': 'v2',
+            'key': {
+              'alg': 'A256CTR',
+              'ext': true,
+              'k': encryptedThumbnail.k,
+              'key_ops': ['encrypt', 'decrypt'],
+              'kty': 'oct'
+            },
+            'iv': encryptedThumbnail.iv,
+            'hashes': {'sha256': encryptedThumbnail.sha256}
+          },
+        if (thumbnail != null) 'thumbnail_info': thumbnail.info,
+        if (thumbnail?.blurhash != null &&
+            file is MatrixImageFile &&
+            file.blurhash == null)
+          'xyz.amorgan.blurhash': thumbnail!.blurhash
+      },
+      if (extraContent != null) ...extraContent,
+    };
+    final eventId = await sendEvent(
+      content,
+      txid: txid,
+      inReplyTo: inReplyTo,
+      editEventId: editEventId,
+    );
+    return eventId;
+  }
+
+  Future<void> handleImageFakeSync(SyncUpdate syncUpdate,
+      {Direction? direction}) async {
+    if (client.database != null) {
+      await client.database?.transaction(() async {
+        await client.handleSync(syncUpdate, direction: direction);
+      });
+    } else {
+      await client.handleSync(syncUpdate, direction: direction);
+    }
+  }
+}
\ No newline at end of file
diff --git a/lib/utils/matrix_sdk_extensions/event_extension.dart b/lib/utils/matrix_sdk_extensions/event_extension.dart
index 358a8a958b..1ba54d9c27 100644
--- a/lib/utils/matrix_sdk_extensions/event_extension.dart
+++ b/lib/utils/matrix_sdk_extensions/event_extension.dart
@@ -46,4 +46,27 @@ extension LocalizedBody on Event {
       .tryGetMap<String, dynamic>('info')
       ?.tryGet<int>('size')
       ?.sizeString;
+
+  Uint8List? _getPlaceHolderMatrixFile(Event event) {
+    if (room.sendingFilePlaceholders.isNotEmpty) {
+      if (status == EventStatus.synced || status == EventStatus.sent) {
+        if (unsigned?.containsKey('transaction_id') == true) {
+          final transactionId = unsigned!['transaction_id'];
+          return room.sendingFilePlaceholders[transactionId]?.bytes;
+        }
+      }
+    }
+    return null;
+  }
+
+  Uint8List? getSendingImageData() {
+    if (status == EventStatus.sending) {
+      return room.sendingFilePlaceholders[eventId]?.bytes;
+    } else if (status == EventStatus.synced) {
+      return _getPlaceHolderMatrixFile(this);
+    } else if (status == EventStatus.sent) {
+      return _getPlaceHolderMatrixFile(this); 
+    }
+    return null;
+  }
 }
diff --git a/pubspec.lock b/pubspec.lock
index 05443b428a..6d5083e7ae 100644
--- a/pubspec.lock
+++ b/pubspec.lock
@@ -1691,7 +1691,7 @@ packages:
     source: hosted
     version: "5.1.0"
   photo_manager:
-    dependency: transitive
+    dependency: "direct main"
     description:
       name: photo_manager
       sha256: bdc4ab1fa9fb064d8ccfea6ab44119f55b220293d7ce2e19eb5a5f998db86c88
diff --git a/pubspec.yaml b/pubspec.yaml
index 0823e986bb..e2b117d489 100644
--- a/pubspec.yaml
+++ b/pubspec.yaml
@@ -114,6 +114,7 @@ dependencies:
   debounce_throttle: ^2.0.0
   fluttertoast: ^8.2.2
   rxdart: ^0.27.7
+  photo_manager: ^2.6.0
 dev_dependencies:
   build_runner: ^2.3.3
   dart_code_metrics: ^5.7.3