diff --git a/assets/l10n/intl_en.arb b/assets/l10n/intl_en.arb
index c1ffb8627..40a1c3f7e 100644
--- a/assets/l10n/intl_en.arb
+++ b/assets/l10n/intl_en.arb
@@ -696,6 +696,7 @@
       }
     }
   },
+  "checkList": "Check list",
   "countParticipants": "{count} participants",
   "@countParticipants": {
     "type": "String",
diff --git a/lib/pages/chat/chat.dart b/lib/pages/chat/chat.dart
index 1103c47fa..dd1d16c91 100644
--- a/lib/pages/chat/chat.dart
+++ b/lib/pages/chat/chat.dart
@@ -275,13 +275,44 @@ class ChatController extends State<ChatPageWithRoom>
     );
   }
 
-  KeyEventResult _shiftEnterKeyHandling(FocusNode node, KeyEvent evt) {
+  KeyEventResult _customEnterKeyHandling(FocusNode node, KeyEvent evt) {
     if (!HardwareKeyboard.instance.isShiftPressed &&
-        evt.logicalKey.keyLabel == 'Enter') {
+        evt.logicalKey.keyLabel == 'Enter' &&
+        (AppConfig.sendOnEnter ?? !PlatformInfos.isMobile)) {
       if (evt is KeyDownEvent) {
         send();
       }
       return KeyEventResult.handled;
+    } else if (evt.logicalKey.keyLabel == 'Enter' && evt is KeyDownEvent) {
+      final currentLineNum = sendController.text
+              .substring(
+                0,
+                sendController.selection.baseOffset,
+              )
+              .split('\n')
+              .length -
+          1;
+      final currentLine = sendController.text.split('\n')[currentLineNum];
+
+      for (final pattern in [
+        '- [ ] ',
+        '- [x] ',
+        '* [ ] ',
+        '* [x] ',
+        '- ',
+        '* ',
+        '+ ',
+      ]) {
+        if (currentLine.startsWith(pattern)) {
+          if (currentLine == pattern) {
+            return KeyEventResult.ignored;
+          }
+          sendController.text += '\n$pattern';
+          return KeyEventResult.handled;
+        }
+      }
+
+      return KeyEventResult.ignored;
     } else {
       return KeyEventResult.ignored;
     }
@@ -289,11 +320,7 @@ class ChatController extends State<ChatPageWithRoom>
 
   @override
   void initState() {
-    inputFocus = FocusNode(
-      onKeyEvent: (AppConfig.sendOnEnter ?? !PlatformInfos.isMobile)
-          ? _shiftEnterKeyHandling
-          : null,
-    );
+    inputFocus = FocusNode(onKeyEvent: _customEnterKeyHandling);
 
     scrollController.addListener(_updateScrollController);
     inputFocus.addListener(_inputFocusListener);
@@ -1154,6 +1181,14 @@ 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 88860a77e..b07d2ae38 100644
--- a/lib/pages/chat/chat_input_row.dart
+++ b/lib/pages/chat/chat_input_row.dart
@@ -123,6 +123,18 @@ 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',