diff --git a/gateway/mirror.py b/gateway/mirror.py
index 4f95746319b25..cee31302c40f7 100644
--- a/gateway/mirror.py
+++ b/gateway/mirror.py
@@ -45,9 +45,13 @@ def mirror_to_session(
             logger.debug("Mirror: no session found for %s:%s:%s", platform, chat_id, thread_id)
             return False
 
+        # Use "user" role for mirrored cron/delivery messages to maintain
+        # proper user/assistant alternation in the conversation history.
+        # Using "assistant" caused two consecutive assistant messages which
+        # confuses models and can cause API rejections on strict providers.
         mirror_msg = {
-            "role": "assistant",
-            "content": message_text,
+            "role": "user",
+            "content": f"[Cron delivery from {source_label}]\n{message_text}",
             "timestamp": datetime.now().isoformat(),
             "mirror": True,
             "mirror_source": source_label,
diff --git a/tests/gateway/test_mirror.py b/tests/gateway/test_mirror.py
index 427e720cd928e..19b16ff4f531c 100644
--- a/tests/gateway/test_mirror.py
+++ b/tests/gateway/test_mirror.py
@@ -161,8 +161,8 @@ def test_successful_mirror(self, tmp_path):
         transcript = sessions_dir / "sess_abc.jsonl"
         assert transcript.exists()
         msg = json.loads(transcript.read_text().strip())
-        assert msg["content"] == "Hello!"
-        assert msg["role"] == "assistant"
+        assert msg["content"] == "[Cron delivery from cli]\nHello!"
+        assert msg["role"] == "user"
         assert msg["mirror"] is True
         assert msg["mirror_source"] == "cli"