diff --git a/ghost/admin/lib/koenig-editor/addon/options/text-expansions.js b/ghost/admin/lib/koenig-editor/addon/options/text-expansions.js
index a6bbc9e8f1..e457a5803c 100644
--- a/ghost/admin/lib/koenig-editor/addon/options/text-expansions.js
+++ b/ghost/admin/lib/koenig-editor/addon/options/text-expansions.js
@@ -8,10 +8,6 @@ export function replaceWithListSection(editor, matches, listTagName) {
     let {range, range: {head, head: {section}}} = editor;
     let text = section.textUntil(head);
 
-    if (section.isListItem) {
-        return;
-    }
-
     // we don't want to convert to a heading if the user has not just
     // finished typing the markdown (eg, they've made a previous
     // heading expansion then Cmd-Z'ed it to get the text back then
@@ -20,6 +16,35 @@ export function replaceWithListSection(editor, matches, listTagName) {
         return;
     }
 
+    if (section.isListItem) {
+        if (section.parent.tagName === listTagName) {
+            return;
+        }
+
+        // toggle all list items to the new list type
+        editor.run((postEditor) => {
+            let listRange = section.parent.toRange();
+            let {post} = editor;
+
+            range = range.extend(-(matches[0].length));
+            postEditor.deleteRange(range);
+
+            let cursorListItem;
+            post.walkMarkerableSections(listRange, (listItem) => {
+                let isCursorListItem = listItem === section;
+                let changedListItem = postEditor.changeSectionTagName(listItem, listTagName);
+
+                if (isCursorListItem) {
+                    cursorListItem = changedListItem;
+                }
+            });
+
+            postEditor.setRange(cursorListItem.headPosition().toRange());
+        });
+
+        return;
+    }
+
     editor.run((postEditor) => {
         range = range.extend(-(matches[0].length));
         let position = postEditor.deleteRange(range);