diff --git a/app/editor/components/CommandMenu.tsx b/app/editor/components/CommandMenu.tsx
index 70fe62a4c..a4142da72 100644
--- a/app/editor/components/CommandMenu.tsx
+++ b/app/editor/components/CommandMenu.tsx
@@ -431,10 +431,12 @@ class CommandMenu<T = MenuItem> extends React.Component<Props<T>, State> {
     }
 
     if (embedItems.length) {
-      items.push({
-        name: "separator",
-      });
-      items = items.concat(embedItems);
+      items = items.concat(
+        {
+          name: "separator",
+        },
+        embedItems
+      );
     }
 
     const filtered = items.filter((item) => {
diff --git a/shared/editor/lib/filterExcessSeparators.ts b/shared/editor/lib/filterExcessSeparators.ts
index 48f6bcf58..4288fb771 100644
--- a/shared/editor/lib/filterExcessSeparators.ts
+++ b/shared/editor/lib/filterExcessSeparators.ts
@@ -12,14 +12,21 @@ export default function filterExcessSeparators(
       return acc;
     }
 
-    // trim double separators looking ahead / behind
+    // trim double separators looking behind
     const prev = items[index - 1];
     if (prev && prev.name === "separator" && item.name === "separator") {
       return acc;
     }
 
+    // trim double separators looking ahead only if we're in the second to last
+    // position and the last position is also a separator (special case)
     const next = items[index + 1];
-    if (next && next.name === "separator" && item.name === "separator") {
+    if (
+      next &&
+      next.name === "separator" &&
+      item.name === "separator" &&
+      index === items.length - 2
+    ) {
       return acc;
     }