diff --git a/packages/editor/src/extensions/outline-list-item/__tests__/outline-list-item.test.ts b/packages/editor/src/extensions/outline-list-item/__tests__/outline-list-item.test.ts
index 673040c39..3be822fbc 100644
--- a/packages/editor/src/extensions/outline-list-item/__tests__/outline-list-item.test.ts
+++ b/packages/editor/src/extensions/outline-list-item/__tests__/outline-list-item.test.ts
@@ -73,6 +73,71 @@ describe("outline list item", () => {
     expect(editor.getJSON()).toMatchSnapshot();
   });
 
+  test("tapping the gutter of a nested item toggles it; a flat item ignores it", () => {
+    const el = outlineList(
+      outlineListItem(["flat item"]),
+      li(
+        [
+          h("p", ["Parent"]),
+          outlineList(
+            outlineListItem(["Child one"]),
+            outlineListItem(["Child two"])
+          )
+        ],
+        { "data-type": "outlineListItem" }
+      )
+    );
+
+    const { editor } = createEditor({
+      initialContent: el.outerHTML,
+      extensions: {
+        outlineList: OutlineList,
+        outlineListItem: OutlineListItem,
+        paragraph: Paragraph
+      }
+    });
+
+    const dom = editor.view.dom as HTMLElement;
+    const nested = dom.querySelector("li.nested");
+    const flat = Array.from(dom.querySelectorAll("li")).find(
+      (item) => !item.classList.contains("nested")
+    );
+    expect(nested).toBeTruthy();
+    expect(flat).toBeTruthy();
+
+    const collapsed = () => {
+      let value: boolean | undefined;
+      editor.state.doc.descendants((node) => {
+        if (
+          node.type.name === OutlineListItem.name &&
+          node.lastChild?.type.name === OutlineList.name
+        )
+          value = node.attrs.collapsed;
+      });
+      return value;
+    };
+
+    const tapGutter = (item: Element) =>
+      item.dispatchEvent(
+        new MouseEvent("mousedown", {
+          button: 0,
+          clientX: -10,
+          clientY: 0,
+          bubbles: true,
+          cancelable: true
+        })
+      );
+
+    expect(collapsed()).toBe(false);
+    tapGutter(nested!);
+    expect(collapsed()).toBe(true);
+    tapGutter(nested!);
+    expect(collapsed()).toBe(false);
+
+    tapGutter(flat!);
+    expect(collapsed()).toBe(false);
+  });
+
   /**
    * Two changes happened:
    * 1. Images were converted from inline nodes to block nodes (https://github.com/streetwriters/notesnook/pull/8563)
diff --git a/packages/editor/src/extensions/outline-list-item/outline-list-item.ts b/packages/editor/src/extensions/outline-list-item/outline-list-item.ts
index b26574b5b..043afc295 100644
--- a/packages/editor/src/extensions/outline-list-item/outline-list-item.ts
+++ b/packages/editor/src/extensions/outline-list-item/outline-list-item.ts
@@ -24,7 +24,6 @@ import {
 } from "@tiptap/core";
 import {
   findParentNodeOfTypeClosestToPos,
-  isClickWithinBounds,
   ensureLeadingParagraph
 } from "../../utils/prosemirror.js";
 import { OutlineList } from "../outline-list/outline-list.js";
@@ -147,14 +146,24 @@ export const OutlineListItem = Node.create<ListItemOptions>({
 
       function onClick(e: MouseEvent | TouchEvent) {
         if (e instanceof MouseEvent && e.button !== 0) return;
-        if (!(e.target instanceof HTMLElement)) return;
         if (!li.classList.contains("nested")) return;
 
         const pos = typeof getPos === "function" ? getPos() : 0;
         if (typeof pos !== "number") return;
 
-        const resolvedPos = editor.state.doc.resolve(pos);
-        if (isClickWithinBounds(e, resolvedPos, "left")) {
+        const point = e instanceof MouseEvent ? e : e.touches[0];
+        if (!point) return;
+
+        const rect = li.getBoundingClientRect();
+        const row = (li.firstElementChild ?? li).getBoundingClientRect();
+        const rtl = getComputedStyle(li).direction === "rtl";
+
+        const withinX = rtl
+          ? point.clientX >= rect.right && point.clientX <= rect.right + 40
+          : point.clientX >= rect.left - 40 && point.clientX <= rect.left;
+        const withinY = point.clientY >= row.top && point.clientY <= row.bottom;
+
+        if (withinX && withinY) {
           e.preventDefault();
           e.stopImmediatePropagation();
           editor.commands.command(({ tr }) => {
diff --git a/packages/editor/styles/styles.css b/packages/editor/styles/styles.css
index b59a9488b..d20fdc0d7 100644
--- a/packages/editor/styles/styles.css
+++ b/packages/editor/styles/styles.css
@@ -657,6 +657,21 @@ p > *::selection {
   border-left: 1px solid var(--hover);
 }
 
+.outline-list > li.nested::after {
+  content: "";
+  position: absolute;
+  top: 0;
+  left: -40px;
+  width: 40px;
+  height: 1lh;
+  cursor: pointer;
+}
+
+.outline-list[dir="rtl"] > li.nested::after {
+  left: unset;
+  right: -40px;
+}
+
 /* IMAGE */
 
 .image-view-content-wrap.ProseMirror-selectednode .resizer::before {