diff --git a/.playwright/tests/checkboxList.spec.ts b/.playwright/tests/checkboxList.spec.ts
index 0348da532..8472a7d42 100644
--- a/.playwright/tests/checkboxList.spec.ts
+++ b/.playwright/tests/checkboxList.spec.ts
@@ -59,4 +59,33 @@ test.describe('checkbox list (web)', () => {
     const html = await getSerializedHtml(page);
     expect(html.match(/<li checked/g)?.length).toBe(1);
   });
+
+  test('clicking checkbox moves cursor', async ({ page }) => {
+    await setEditorHtml(
+      page,
+      '<html><ul data-type="checkbox"><li>one</li><li>two</li></ul></html>'
+    );
+
+    const editor = editorLocator(page);
+    const checkbox = editor.locator('input[type="checkbox"]').first();
+    await checkbox.click();
+
+    const selection = await editor.evaluate(() => {
+      const s = window.getSelection();
+      if (!s || s.rangeCount === 0) {
+        return null;
+      }
+      const range = s.getRangeAt(0);
+      return {
+        startOffset: range.startOffset,
+        endOffset: range.endOffset,
+        collapsed: range.collapsed,
+      };
+    });
+    expect(selection).toEqual({
+      startOffset: 3,
+      endOffset: 3,
+      collapsed: true,
+    });
+  });
 });
diff --git a/src/web/EnrichedTextInput.tsx b/src/web/EnrichedTextInput.tsx
index 1002b647c..7d118ff3f 100644
--- a/src/web/EnrichedTextInput.tsx
+++ b/src/web/EnrichedTextInput.tsx
@@ -18,12 +18,7 @@ import {
   nativePosToTiptapPos,
   nativeLeafText,
 } from './nativeMappers/positionMapping';
-import {
-  useEditor,
-  EditorContent,
-  type ChainedCommands,
-  Editor,
-} from '@tiptap/react';
+import { useEditor, EditorContent, Editor } from '@tiptap/react';
 import Document from '@tiptap/extension-document';
 import Paragraph from '@tiptap/extension-paragraph';
 import Text from '@tiptap/extension-text';
@@ -92,13 +87,8 @@ import {
 import { assertBrowserEnvironment } from './utils/assertBrowserEnvironment';
 import { runSafelyInEditor } from './utils/runSafelyInEditor';
 import { useLinkPress } from './htmlExtensions/useLinkPress';
-
-function runFocused(
-  editor: Editor,
-  apply: (chain: ChainedCommands) => ChainedCommands
-) {
-  runSafelyInEditor(editor, (e) => apply(e.chain().focus()).run());
-}
+import { handleCheckboxPress } from './htmlExtensions/handleCheckboxPress';
+import { runFocused } from './utils/runFocused';
 
 export const EnrichedTextInput = ({
   ref,
@@ -292,7 +282,12 @@ export const EnrichedTextInput = ({
       editorProps: {
         handleKeyDown: (view, event) => handleKeyDown(view.state.doc, event),
         handleDOMEvents: {
-          click: (_view, event) => handleLinkPress(event),
+          click: (view, event) => {
+            if (handleCheckboxPress(event, editor, view)) {
+              return true;
+            }
+            return handleLinkPress(event);
+          },
           mousedown: (_view, event) => handleLinkMouseDown(event),
         },
         handlePaste: (_view, event) =>
diff --git a/src/web/htmlExtensions/handleCheckboxPress.ts b/src/web/htmlExtensions/handleCheckboxPress.ts
new file mode 100644
index 000000000..5e8f1f14f
--- /dev/null
+++ b/src/web/htmlExtensions/handleCheckboxPress.ts
@@ -0,0 +1,19 @@
+import { Editor } from '@tiptap/core';
+import type { EditorView } from '@tiptap/pm/view';
+import { runFocused } from '../utils/runFocused';
+
+export function handleCheckboxPress(
+  event: MouseEvent,
+  editor: Editor,
+  view: EditorView
+): boolean {
+  const target = event.target;
+  if (target instanceof HTMLInputElement && target.type === 'checkbox') {
+    const position = view.posAtDOM(target, 0);
+    const node = view.state.doc.nodeAt(position);
+    if (!node) return false;
+    runFocused(editor, (c) => c.setTextSelection(position + node.nodeSize - 1));
+    return true;
+  }
+  return false;
+}
diff --git a/src/web/utils/runFocused.ts b/src/web/utils/runFocused.ts
new file mode 100644
index 000000000..a1f97f9da
--- /dev/null
+++ b/src/web/utils/runFocused.ts
@@ -0,0 +1,8 @@
+import { Editor, type ChainedCommands } from '@tiptap/core';
+import { runSafelyInEditor } from './runSafelyInEditor';
+export function runFocused(
+  editor: Editor,
+  apply: (chain: ChainedCommands) => ChainedCommands
+) {
+  runSafelyInEditor(editor, (e) => apply(e.chain().focus()).run());
+}