diff --git a/resources/js/wysiwyg/lexical/list/LexicalListItemNode.ts b/resources/js/wysiwyg/lexical/list/LexicalListItemNode.ts
index a7b04d476..2a1b698b1 100644
--- a/resources/js/wysiwyg/lexical/list/LexicalListItemNode.ts
+++ b/resources/js/wysiwyg/lexical/list/LexicalListItemNode.ts
@@ -36,6 +36,7 @@ import {$createListNode, $isListNode} from './LexicalListNode';
 import {mergeLists} from './formatList';
 import {isNestedListNode} from './utils';
 import {el} from "../../utils/dom";
+import {$escapeListAtItem} from "../../utils/lists";
 
 export type SerializedListItemNode = Spread<
   {
@@ -273,21 +274,13 @@ export class ListItemNode extends ElementNode {
     restoreSelection = true,
   ): ListItemNode | ParagraphNode | null {
 
-    if (this.getTextContent().trim() === '' && this.isLastChild()) {
-      const list = this.getParentOrThrow<ListNode>();
-      const parentListItem = list.getParent();
-      if ($isListItemNode(parentListItem)) {
-        // Un-nest list item if empty nested item
-        parentListItem.insertAfter(this);
-        this.selectStart();
-        return null;
-      } else {
-        // Insert empty paragraph after list if adding after last empty child
-        const paragraph = $createParagraphNode();
-        list.insertAfter(paragraph, restoreSelection);
-        this.remove();
-        return paragraph;
-      }
+    // If we're adding a new empty item, and coming from an empty item,
+    // take that as a desire to break from the current list level.
+    // Intended to be a bit more lenient on the last list item hence ignores whitespace,
+    // which allows empty items to be listed with just a space (except for last).
+    const textContent = this.getTextContent();
+    if (textContent === '' || (textContent.trim() === '' && this.isLastChild())) {
+        return $escapeListAtItem(this);
     }
 
     const newElement = $createListItemNode(
diff --git a/resources/js/wysiwyg/lexical/list/__tests__/unit/LexicalListItemNode.test.ts b/resources/js/wysiwyg/lexical/list/__tests__/unit/LexicalListItemNode.test.ts
index 10ff0fc66..48fa2faf8 100644
--- a/resources/js/wysiwyg/lexical/list/__tests__/unit/LexicalListItemNode.test.ts
+++ b/resources/js/wysiwyg/lexical/list/__tests__/unit/LexicalListItemNode.test.ts
@@ -9,12 +9,12 @@
 import {
   $createParagraphNode,
   $createRangeSelection,
-  $getRoot, LexicalEditor,
+  $getRoot, LexicalEditor, LexicalNode, ParagraphNode,
   TextNode,
 } from 'lexical';
 import {
   createTestContext, destroyFromContext,
-  expectHtmlToBeEqual,
+  expectHtmlToBeEqual, expectNodeShapeToMatch,
   html,
 } from 'lexical/__tests__/utils';
 
@@ -1200,6 +1200,70 @@ describe('LexicalListItemNode tests', () => {
           </ul>`,
       );
     });
+
+    test('new items after empty top-level items splits the list in two, and inserts a paragraph inbetween', () => {
+      let newItem: LexicalNode|null = null;
+      const input = `<ul>
+        <li>Item A</li>        
+        <li></li>        
+        <li>Item C</li>        
+        </ul>`;
+
+      editor.updateAndCommit(() => {
+        const root = $getRoot();
+        root.append(...$htmlToBlockNodes(editor, input));
+        const list = root.getFirstChild() as ListNode;
+        const itemB = list.getChildAtIndex(1) as ListItemNode;
+
+        newItem = itemB.insertNewAfter($createRangeSelection());
+      });
+
+      expect(newItem).toBeInstanceOf(ParagraphNode);
+
+      expectNodeShapeToMatch(editor, [
+        {
+          type: 'list',
+          children: [{type: 'listitem', children: [{text: 'Item A'}]}],
+        },
+        {
+          type: 'paragraph',
+        },
+        {
+          type: 'list',
+          children: [{type: 'listitem', children: [{text: 'Item C'}]}],
+        }
+      ])
+    });
+
+    test('new items after last empty top-level inserts a new paragraph below, and removes the list item', () => {
+      let newItem: LexicalNode|null = null;
+      const input = `<ul>
+        <li>Item A</li>        
+        <li>Item B</li>        
+        <li></li>        
+        </ul>`;
+
+      editor.updateAndCommit(() => {
+        const root = $getRoot();
+        root.append(...$htmlToBlockNodes(editor, input));
+        const list = root.getFirstChild() as ListNode;
+        const itemC = list.getChildAtIndex(2) as ListItemNode;
+
+        newItem = itemC.insertNewAfter($createRangeSelection());
+      });
+
+      expect(newItem).toBeInstanceOf(ParagraphNode);
+
+      expectNodeShapeToMatch(editor, [
+        {
+          type: 'list',
+          children: [{type: 'listitem', children: [{text: 'Item A'}]}, {type: 'listitem', children: [{text: 'Item B'}]}],
+        },
+        {
+          type: 'paragraph',
+        },
+      ])
+    });
   });
 
   test('$createListItemNode()', async () => {
diff --git a/resources/js/wysiwyg/utils/lists.ts b/resources/js/wysiwyg/utils/lists.ts
index 3deb9dfb6..cdbaba6fb 100644
--- a/resources/js/wysiwyg/utils/lists.ts
+++ b/resources/js/wysiwyg/utils/lists.ts
@@ -1,7 +1,7 @@
-import {$createTextNode, $getSelection, BaseSelection, LexicalEditor, TextNode} from "lexical";
+import {$createParagraphNode, $createTextNode, $getSelection, BaseSelection, LexicalEditor, ParagraphNode, TextNode} from "lexical";
 import {$getBlockElementNodesInSelection, $selectNodes, $toggleSelection} from "./selection";
 import {$sortNodes, nodeHasInset} from "./nodes";
-import {$createListItemNode, $createListNode, $isListItemNode, $isListNode, ListItemNode} from "@lexical/list";
+import {$createListItemNode, $createListNode, $isListItemNode, $isListNode, ListItemNode, ListNode} from "@lexical/list";
 
 
 export function $nestListItem(node: ListItemNode): ListItemNode {
@@ -186,4 +186,31 @@ export function $setInsetForSelection(editor: LexicalEditor, change: number): vo
     }
 
     $toggleSelection(editor);
-}
\ No newline at end of file
+}
+
+export function $escapeListAtItem(item: ListItemNode): ParagraphNode|null {
+    const list = item.getParentOrThrow<ListNode>();
+    const parentListItem = list.getParent();
+
+    // Un-nest list item if it's an empty nested item
+    if ($isListItemNode(parentListItem)) {
+        parentListItem.insertAfter(item);
+        item.selectStart();
+        return null;
+    }
+
+    // If we're anywhere but at the end, split the list, with following items
+    // moved into their own new list.
+    if (!item.isLastChild()) {
+        const afterSiblings = item.getNextSiblings();
+        const newList = $createListNode(list.getListType());
+        newList.append(...afterSiblings);
+        list.insertAfter(newList);
+    }
+
+    // Insert a new empty paragraph to land on after our list
+    const paragraph = $createParagraphNode();
+    list.insertAfter(paragraph, true);
+    item.remove();
+    return paragraph;
+}