diff --git a/apps/web/src/components/editor/table-of-contents.tsx b/apps/web/src/components/editor/table-of-contents.tsx
index 11892b7e3e..7ad164c5eb 100644
--- a/apps/web/src/components/editor/table-of-contents.tsx
+++ b/apps/web/src/components/editor/table-of-contents.tsx
@@ -149,7 +149,7 @@ function TableOfContents(props: TableOfContentsProps) {
                     key={t.id}
                     sx={{
                       textAlign: "left",
-                      paddingLeft: `${t.level * 5}px`,
+                      paddingLeft: `${t.level * 5 + (t.level - 1) * 5}px`,
                       py: 1,
                       pr: 1,
                       borderLeft: "5px solid transparent",
diff --git a/apps/web/src/components/editor/tiptap.tsx b/apps/web/src/components/editor/tiptap.tsx
index ec5378c38e..7b03c2d7e0 100644
--- a/apps/web/src/components/editor/tiptap.tsx
+++ b/apps/web/src/components/editor/tiptap.tsx
@@ -245,10 +245,13 @@ function TipTap(props: TipTapProps) {
       onDestroy: () => {
         useEditorManager.getState().setEditor(id);
       },
-      onTransaction: ({ editor }) => {
+      onTransaction: ({ editor, transaction }) => {
         useEditorManager.getState().updateEditor(id, {
           canRedo: editor.can().redo(),
-          canUndo: editor.can().undo()
+          canUndo: editor.can().undo(),
+          tableOfContents: transaction.getMeta("isUpdatingContent")
+            ? getTableOfContents(editor.view.dom)
+            : useEditorManager.getState().getEditor(id)?.tableOfContents
         });
       },
       copyToClipboard(text, html) {
@@ -487,6 +490,7 @@ function toIEditor(editor: Editor): IEditor {
         ?.chain()
         .command(({ tr }) => {
           tr.setMeta("preventSave", true);
+          tr.setMeta("isUpdatingContent", true);
           return true;
         })
         .setContent(content, false, { preserveWhitespace: true })