diff --git a/apps/client/src/widgets/sidebar/TableOfContents.tsx b/apps/client/src/widgets/sidebar/TableOfContents.tsx
index 483ddb1793..fdf616ee26 100644
--- a/apps/client/src/widgets/sidebar/TableOfContents.tsx
+++ b/apps/client/src/widgets/sidebar/TableOfContents.tsx
@@ -1,6 +1,6 @@
 import "./TableOfContents.css";
 
-import { CKTextEditor, ModelElement } from "@triliumnext/ckeditor5";
+import { attributeChangeAffectsHeading, CKTextEditor, ModelElement } from "@triliumnext/ckeditor5";
 import clsx from "clsx";
 import { useCallback, useEffect, useRef, useState } from "preact/hooks";
 
@@ -170,11 +170,14 @@ function EditableTextTableOfContents() {
 
             const affectsHeadings = changes.some( change => {
                 return (
-                    change.type === 'insert' || change.type === 'remove' || (change.type === 'attribute' && change.attributeKey === 'headingLevel')
+                    change.type === 'insert' || change.type === 'remove' ||
+                    (change.type === 'attribute' && attributeChangeAffectsHeading(change, textEditor))
                 );
             });
             if (affectsHeadings) {
-                setHeadings(extractTocFromTextEditor(textEditor));
+                requestAnimationFrame(() => {
+                    setHeadings(extractTocFromTextEditor(textEditor));
+                });
             }
         };
 
diff --git a/packages/ckeditor5/src/index.ts b/packages/ckeditor5/src/index.ts
index 7f005b4f74..ca51d92d7b 100644
--- a/packages/ckeditor5/src/index.ts
+++ b/packages/ckeditor5/src/index.ts
@@ -11,6 +11,7 @@ export type { EditorConfig, MentionFeed, MentionFeedObjectItem, ModelNode, Model
 export type { TemplateDefinition } from "ckeditor5-premium-features";
 export { default as buildExtraCommands } from "./extra_slash_commands.js";
 export { default as getCkLocale } from "./i18n.js";
+export * from "./utils.js";
 
 // Import with sideffects to ensure that type augmentations are present.
 import "@triliumnext/ckeditor5-math";
diff --git a/packages/ckeditor5/src/utils.ts b/packages/ckeditor5/src/utils.ts
new file mode 100644
index 0000000000..4ed648d114
--- /dev/null
+++ b/packages/ckeditor5/src/utils.ts
@@ -0,0 +1,28 @@
+import type { DifferItemAttribute, Editor, ModelDocumentFragment, ModelElement, ModelNode } from "ckeditor5";
+
+function hasHeadingAncestor(node: ModelElement | ModelNode | ModelDocumentFragment | null): boolean {
+    let current: ModelElement | ModelNode | ModelDocumentFragment | null = node;
+    while (current) {
+        if (!!current && current.is('element') && (current as ModelElement).name.startsWith("heading")) return true;
+        current = current.parent;
+    }
+    return false;
+}
+
+export function attributeChangeAffectsHeading(change: DifferItemAttribute, editor: Editor): boolean {
+    if (change.type !== "attribute") return false;
+
+    // Fast checks on range boundaries
+    if (hasHeadingAncestor(change.range.start.parent) || hasHeadingAncestor(change.range.end.parent)) {
+        return true;
+    }
+
+    // Robust check across the whole changed range
+    const range = editor.model.createRange(change.range.start, change.range.end);
+    for (const item of range.getItems()) {
+        const baseNode = item.is("$textProxy") ? item.parent : item;
+        if (hasHeadingAncestor(baseNode)) return true;
+    }
+
+    return false;
+}