diff --git a/lib/pages/chat/events/html_message.dart b/lib/pages/chat/events/html_message.dart
index 7aca3154b..5e57b128c 100644
--- a/lib/pages/chat/events/html_message.dart
+++ b/lib/pages/chat/events/html_message.dart
@@ -8,7 +8,9 @@ import 'package:html/dom.dart' as dom;
 import 'package:html/parser.dart' as parser;
 import 'package:matrix/matrix.dart';
 
+import 'package:fluffychat/utils/event_checkbox_extension.dart';
 import 'package:fluffychat/widgets/avatar.dart';
+import 'package:fluffychat/widgets/future_loading_dialog.dart';
 import 'package:fluffychat/widgets/mxc_image.dart';
 import '../../../utils/url_launcher.dart';
 
@@ -19,6 +21,8 @@ class HtmlMessage extends StatelessWidget {
   final double fontSize;
   final TextStyle linkStyle;
   final void Function(LinkableElement) onOpen;
+  final String? eventId;
+  final Set<Event>? checkboxCheckedEvents;
 
   const HtmlMessage({
     super.key,
@@ -28,6 +32,8 @@ class HtmlMessage extends StatelessWidget {
     required this.linkStyle,
     this.textColor = Colors.black,
     required this.onOpen,
+    this.eventId,
+    this.checkboxCheckedEvents,
   });
 
   /// Keep in sync with: https://spec.matrix.org/latest/client-server-api/#mroommessage-msgtypes
@@ -218,6 +224,24 @@ class HtmlMessage extends StatelessWidget {
         if (!{'ol', 'ul'}.contains(node.parent?.localName)) {
           continue block;
         }
+        final eventId = this.eventId;
+
+        final isCheckbox = node.className == 'task-list-item';
+        final checkboxIndex = isCheckbox
+            ? node.rootElement
+                    .getElementsByClassName('task-list-item')
+                    .indexOf(node) +
+                1
+            : null;
+        final checkedByReaction = !isCheckbox
+            ? null
+            : checkboxCheckedEvents?.firstWhereOrNull(
+                (event) => event.checkedCheckboxId == checkboxIndex,
+              );
+        final staticallyChecked = !isCheckbox
+            ? false
+            : node.children.first.attributes['checked'] == 'true';
+
         return WidgetSpan(
           child: Padding(
             padding: EdgeInsets.only(left: fontSize),
@@ -231,6 +255,42 @@ class HtmlMessage extends StatelessWidget {
                       text:
                           '${(node.parent?.nodes.whereType<dom.Element>().toList().indexOf(node) ?? 0) + (int.tryParse(node.parent?.attributes['start'] ?? '1') ?? 1)}. ',
                     ),
+                  if (node.className == 'task-list-item')
+                    WidgetSpan(
+                      child: Padding(
+                        padding: const EdgeInsets.symmetric(horizontal: 8.0),
+                        child: SizedBox.square(
+                          dimension: fontSize,
+                          child: Checkbox.adaptive(
+                            checkColor: textColor,
+                            side: BorderSide(color: textColor),
+                            activeColor: textColor.withAlpha(64),
+                            visualDensity: VisualDensity.compact,
+                            value:
+                                staticallyChecked || checkedByReaction != null,
+                            onChanged: eventId == null ||
+                                    checkboxIndex == null ||
+                                    staticallyChecked ||
+                                    !room.canSendDefaultMessages ||
+                                    (checkedByReaction != null &&
+                                        checkedByReaction.senderId !=
+                                            room.client.userID)
+                                ? null
+                                : (_) => showFutureLoadingDialog(
+                                      context: context,
+                                      future: () => checkedByReaction != null
+                                          ? room.redactEvent(
+                                              checkedByReaction.eventId,
+                                            )
+                                          : room.checkCheckbox(
+                                              eventId,
+                                              checkboxIndex,
+                                            ),
+                                    ),
+                          ),
+                        ),
+                      ),
+                    ),
                   ..._renderWithLineBreaks(
                     node.nodes,
                     context,
@@ -446,11 +506,9 @@ class HtmlMessage extends StatelessWidget {
 
   @override
   Widget build(BuildContext context) {
+    final element = parser.parse(html).body ?? dom.Element.html('');
     return Text.rich(
-      _renderHtml(
-        parser.parse(html).body ?? dom.Element.html(''),
-        context,
-      ),
+      _renderHtml(element, context),
       style: TextStyle(
         fontSize: fontSize,
         color: textColor,
@@ -516,3 +574,7 @@ extension on String {
     return colorValue == null ? null : Color(colorValue);
   }
 }
+
+extension on dom.Element {
+  dom.Element get rootElement => parent?.rootElement ?? this;
+}
diff --git a/lib/pages/chat/events/message_content.dart b/lib/pages/chat/events/message_content.dart
index 116aaf4ef..8c72cae3b 100644
--- a/lib/pages/chat/events/message_content.dart
+++ b/lib/pages/chat/events/message_content.dart
@@ -13,6 +13,7 @@ import 'package:fluffychat/utils/matrix_sdk_extensions/matrix_locals.dart';
 import 'package:fluffychat/widgets/avatar.dart';
 import 'package:fluffychat/widgets/matrix.dart';
 import '../../../config/app_config.dart';
+import '../../../utils/event_checkbox_extension.dart';
 import '../../../utils/platform_infos.dart';
 import '../../../utils/url_launcher.dart';
 import '../../bootstrap/bootstrap_dialog.dart';
@@ -204,6 +205,11 @@ class MessageContent extends StatelessWidget {
                     decorationColor: linkColor,
                   ),
                   onOpen: (url) => UrlLauncher(context, url.url).launchUrl(),
+                  eventId: event.eventId,
+                  checkboxCheckedEvents: event.aggregatedEvents(
+                    timeline,
+                    EventCheckboxRoomExtension.relationshipType,
+                  ),
                 ),
               );
             }
diff --git a/lib/utils/event_checkbox_extension.dart b/lib/utils/event_checkbox_extension.dart
new file mode 100644
index 000000000..cf3832ba6
--- /dev/null
+++ b/lib/utils/event_checkbox_extension.dart
@@ -0,0 +1,27 @@
+import 'package:matrix/matrix.dart';
+
+extension EventCheckboxRoomExtension on Room {
+  static const String relationshipType = 'im.fluffychat.checkboxes';
+  Future<String?> checkCheckbox(
+    String eventId,
+    int checkboxId, {
+    String? txid,
+  }) =>
+      sendEvent(
+        {
+          'm.relates_to': {
+            'rel_type': relationshipType,
+            'event_id': eventId,
+            'checkbox_id': checkboxId,
+          },
+        },
+        type: EventTypes.Reaction,
+        txid: txid,
+      );
+}
+
+extension EventCheckboxExtension on Event {
+  int? get checkedCheckboxId => content
+      .tryGetMap<String, Object?>('m.relates_to')
+      ?.tryGet<int>('checkbox_id');
+}
diff --git a/pubspec.lock b/pubspec.lock
index f1c892e49..084b31477 100644
--- a/pubspec.lock
+++ b/pubspec.lock
@@ -1150,10 +1150,11 @@ packages:
   matrix:
     dependency: "direct main"
     description:
-      name: matrix
-      sha256: "7d15fdbc760be7e40c58bb65e03baa8241b1e31db2bc67dab61883aabc083a85"
-      url: "https://pub.dev"
-    source: hosted
+      path: "."
+      ref: "krille/add-markdown-checkboxes"
+      resolved-ref: f3bb654ac2cda19bdd8a35fb46846018acd01a89
+      url: "https://github.com/famedly/matrix-dart-sdk.git"
+    source: git
     version: "0.40.0"
   meta:
     dependency: transitive
diff --git a/pubspec.yaml b/pubspec.yaml
index a3fc68d61..61efd69b9 100644
--- a/pubspec.yaml
+++ b/pubspec.yaml
@@ -61,7 +61,10 @@ dependencies:
   just_audio: ^0.9.39
   latlong2: ^0.9.1
   linkify: ^5.0.0
-  matrix: ^0.40.0
+  matrix:
+    git:
+      url: https://github.com/famedly/matrix-dart-sdk.git
+      ref: krille/add-markdown-checkboxes
   mime: ^1.0.6
   native_imaging: ^0.2.0
   opus_caf_converter_dart: ^1.0.1
@@ -140,4 +143,4 @@ dependency_overrides:
       url: https://github.com/ThexXTURBOXx/flutter_web_auth_2.git
       ref: 3.x-without-v1
       path: flutter_web_auth_2
-  win32: 5.5.3
+  win32: 5.5.3
\ No newline at end of file