diff --git a/src/features/browser-assistant/sort.ts b/src/features/browser-assistant/sort.ts
index e41ee26..cdb3eed 100644
--- a/src/features/browser-assistant/sort.ts
+++ b/src/features/browser-assistant/sort.ts
@@ -14,6 +14,20 @@ export function compareText(left: string, right: string) {
   });
 }
 
+function compareOptionalText(left: string | null | undefined, right: string | null | undefined) {
+  const leftValue = left?.trim() ?? "";
+  const rightValue = right?.trim() ?? "";
+
+  const leftEmpty = leftValue.length === 0;
+  const rightEmpty = rightValue.length === 0;
+
+  if (leftEmpty && rightEmpty) return 0;
+  if (leftEmpty) return 1;
+  if (rightEmpty) return -1;
+
+  return compareText(leftValue, rightValue);
+}
+
 export function compareProfileId(left: string, right: string) {
   const leftKey = profileSortKeyValue(left);
   const rightKey = profileSortKeyValue(right);
@@ -27,7 +41,7 @@ export function sortProfiles(items: ProfileSummary[], sortKey: ProfileSortKey) {
   return profiles.sort((left, right) => {
     if (sortKey === "email") {
       return (
-        compareText(left.email ?? "", right.email ?? "") ||
+        compareOptionalText(left.email, right.email) ||
         compareText(left.name, right.name) ||
         compareProfileId(left.id, right.id)
       );
@@ -53,9 +67,9 @@ export function sortBookmarks(items: BookmarkSummary[], sortKey: BookmarkSortKey
   const bookmarks = [...items];
   return bookmarks.sort((left, right) => {
     if (sortKey === "url") {
-      return compareText(left.url, right.url);
+      return compareOptionalText(left.url, right.url) || compareText(left.title, right.title);
     }
-    return compareText(left.title, right.title) || compareText(left.url, right.url);
+    return compareOptionalText(left.title, right.title) || compareText(left.url, right.url);
   });
 }