diff --git a/.github/workflows/versions.env b/.github/workflows/versions.env
index 3cad68ef4..1d646f732 100644
--- a/.github/workflows/versions.env
+++ b/.github/workflows/versions.env
@@ -1,2 +1,2 @@
-FLUTTER_VERSION=3.32.0
+FLUTTER_VERSION=3.32.1
 JAVA_VERSION=17
diff --git a/lib/pages/chat/chat.dart b/lib/pages/chat/chat.dart
index 1ddf8cc6e..421836958 100644
--- a/lib/pages/chat/chat.dart
+++ b/lib/pages/chat/chat.dart
@@ -1780,14 +1780,6 @@ class ChatController extends State<ChatPageWithRoom>
     if (choice == 'location') {
       sendLocationAction();
     }
-    if (choice == 'checklist') {
-      if (sendController.text.isEmpty) {
-        sendController.text = '- [ ] ';
-      } else {
-        sendController.text += '\n- [ ] ';
-      }
-      inputFocus.requestFocus();
-    }
   }
 
   unpinEvent(String eventId) async {
diff --git a/lib/pages/chat/chat_input_row.dart b/lib/pages/chat/chat_input_row.dart
index 01eafc874..a598d9b11 100644
--- a/lib/pages/chat/chat_input_row.dart
+++ b/lib/pages/chat/chat_input_row.dart
@@ -124,18 +124,6 @@ class ChatInputRow extends StatelessWidget {
                   onSelected: controller.onAddPopupMenuButtonSelected,
                   itemBuilder: (BuildContext context) =>
                       <PopupMenuEntry<String>>[
-                    PopupMenuItem<String>(
-                      value: 'checklist',
-                      child: ListTile(
-                        leading: CircleAvatar(
-                          backgroundColor: theme.colorScheme.onPrimaryContainer,
-                          foregroundColor: theme.colorScheme.primaryContainer,
-                          child: const Icon(Icons.check_circle_outlined),
-                        ),
-                        title: Text(L10n.of(context).checkList),
-                        contentPadding: const EdgeInsets.all(0),
-                      ),
-                    ),
                     if (PlatformInfos.isMobile)
                       PopupMenuItem<String>(
                         value: 'location',
diff --git a/lib/pages/chat/events/html_message.dart b/lib/pages/chat/events/html_message.dart
index e90727b7b..d05374dc3 100644
--- a/lib/pages/chat/events/html_message.dart
+++ b/lib/pages/chat/events/html_message.dart
@@ -1,3 +1,4 @@
+import 'package:flutter/cupertino.dart';
 import 'package:flutter/material.dart';
 
 import 'package:collection/collection.dart';
@@ -508,12 +509,11 @@ class HtmlMessage extends StatelessWidget {
                       child: Padding(
                         padding: const EdgeInsets.symmetric(horizontal: 8.0),
                         child: SizedBox.square(
-                          dimension: fontSize,
-                          child: Checkbox.adaptive(
+                          dimension: fontSize + 2,
+                          child: CupertinoCheckbox(
                             checkColor: textColor,
                             side: BorderSide(color: textColor),
                             activeColor: textColor.withAlpha(64),
-                            visualDensity: VisualDensity.compact,
                             value:
                                 staticallyChecked || checkedByReaction != null,
                             onChanged: eventId == null ||
diff --git a/lib/utils/markdown_context_builder.dart b/lib/utils/markdown_context_builder.dart
index ac6348553..9404d3504 100644
--- a/lib/utils/markdown_context_builder.dart
+++ b/lib/utils/markdown_context_builder.dart
@@ -54,6 +54,35 @@ Widget markdownContextBuilder(
             ContextMenuController.removeAny();
           },
         ),
+        ContextMenuButtonItem(
+          label: l10n.checkList,
+          onPressed: () {
+            final text = controller.text;
+            final selection = controller.selection;
+
+            var start = selection.textBefore(text).lastIndexOf('\n');
+            if (start == -1) start = 0;
+            final end = selection.end;
+
+            final fullLineSelection =
+                TextSelection(baseOffset: start, extentOffset: end);
+
+            const checkBox = '- [ ]';
+
+            final replacedRange = fullLineSelection
+                .textInside(text)
+                .split('\n')
+                .map(
+                  (line) => line.startsWith(checkBox) || line.isEmpty
+                      ? line
+                      : '$checkBox $line',
+                )
+                .join('\n');
+            controller.text =
+                controller.text.replaceRange(start, end, replacedRange);
+            ContextMenuController.removeAny();
+          },
+        ),
         ContextMenuButtonItem(
           label: l10n.boldText,
           onPressed: () {