diff --git a/lib/editors/heuristics.dart b/lib/editors/heuristics.dart
index 6e9831f9..b7c6e3e8 100644
--- a/lib/editors/heuristics.dart
+++ b/lib/editors/heuristics.dart
@@ -12,17 +12,11 @@ EditorHeuristicResult autoAddBulletList(
     return null;
   }
 
-  // Only when getting a new line
+  // Only when adding a new line
   if (curText[cursorPos - 1] != '\n') {
     return null;
   }
 
-  // Only add the bullets at the end of the document
-  // FIXME: We should do this anywhere
-  if (curText.length != cursorPos) {
-    return null;
-  }
-
   var prevLineStart = curText.lastIndexOf('\n', cursorPos - 2);
   prevLineStart = prevLineStart == -1 ? 0 : prevLineStart + 1;
   var prevLine = curText.substring(prevLineStart, cursorPos - 1);
@@ -35,6 +29,11 @@ EditorHeuristicResult autoAddBulletList(
 
   var indent = match.group(1) ?? "";
   var text = curText.substring(0, cursorPos) + indent + match.group(2) + ' ';
+  if (cursorPos == curText.length) {
+    return EditorHeuristicResult(text, text.length);
+  }
 
-  return EditorHeuristicResult(text, text.length);
+  text += '\n' + curText.substring(cursorPos + 1);
+  var extraChars = indent.length + match.group(2).length + 1;
+  return EditorHeuristicResult(text, cursorPos + extraChars);
 }
diff --git a/test/editor_heuristics_test.dart b/test/editor_heuristics_test.dart
index 9c1f037f..8298e979 100644
--- a/test/editor_heuristics_test.dart
+++ b/test/editor_heuristics_test.dart
@@ -11,7 +11,7 @@ void main() {
       expect(result, null);
     });
 
-    test('Adds a bullet item', () {
+    test('Adds a bullet point at the end', () {
       var origText = "Hello\n* One";
       var newText = "Hello\n* One\n";
 
@@ -19,5 +19,14 @@ void main() {
       expect(result.text, "Hello\n* One\n* ");
       expect(result.cursorPos, result.text.length);
     });
+
+    test('Adds a bullet point in the middle', () {
+      var origText = "Hello\n* One\n* Three";
+      var newText = "Hello\n* One\n\n* Three";
+
+      var result = autoAddBulletList(origText, newText, 12);
+      expect(result.text, "Hello\n* One\n* \n* Three");
+      expect(result.cursorPos, 14);
+    });
   });
 }