diff --git a/run_agent.py b/run_agent.py
index e81bf3b93e7ee..26adb4a083acb 100644
--- a/run_agent.py
+++ b/run_agent.py
@@ -1466,6 +1466,12 @@ def _apply_persist_user_message_override(self, messages: List[Dict]) -> None:
         history. When an override is configured for the active turn, mutate the
         in-memory messages list in place so both persistence and returned
         history stay clean.
+
+        When the original content is a list (multimodal content blocks, e.g.
+        images) and the override is a string, merge the override text with the
+        existing non-text content blocks instead of clobbering them.  This
+        prevents image content blocks from being silently dropped.  Fix for
+        #44242.
         """
         idx = getattr(self, "_persist_user_message_idx", None)
         override = getattr(self, "_persist_user_message_override", None)
@@ -1474,7 +1480,24 @@ def _apply_persist_user_message_override(self, messages: List[Dict]) -> None:
         if 0 <= idx < len(messages):
             msg = messages[idx]
             if isinstance(msg, dict) and msg.get("role") == "user":
-                msg["content"] = override
+                original_content = msg.get("content")
+                # When original content is a list (multimodal) and override
+                # is a plain string, merge rather than clobber so image/audio
+                # content blocks survive persistence.
+                if isinstance(original_content, list) and isinstance(override, str):
+                    merged: list[dict] = []
+                    text_replaced = False
+                    for block in original_content:
+                        if isinstance(block, dict) and block.get("type") == "text":
+                            merged.append({"type": "text", "text": override})
+                            text_replaced = True
+                        else:
+                            merged.append(block)
+                    if not text_replaced:
+                        merged.insert(0, {"type": "text", "text": override})
+                    msg["content"] = merged
+                else:
+                    msg["content"] = override
 
     def _persist_session(self, messages: List[Dict], conversation_history: List[Dict] = None):
         """Save session state to both JSON log and SQLite on any exit path.
diff --git a/tests/run_agent/test_run_agent.py b/tests/run_agent/test_run_agent.py
index 9d97693aa7f66..c2e028c1b22f4 100644
--- a/tests/run_agent/test_run_agent.py
+++ b/tests/run_agent/test_run_agent.py
@@ -6179,6 +6179,61 @@ def test_persist_session_rewrites_current_turn_user_message(self, agent):
         first_db_write = agent._session_db.append_message.call_args_list[0].kwargs
         assert first_db_write["content"] == "Hello there"
 
+    def test_persist_session_preserves_image_blocks(self, agent):
+        """Multimodal content blocks must survive the persist override (fixes #44242)."""
+        agent._session_db = MagicMock()
+        agent.session_id = "session-123"
+        agent._last_flushed_db_idx = 0
+        agent._persist_user_message_idx = 0
+        agent._persist_user_message_override = "Describe this image"
+        messages = [
+            {
+                "role": "user",
+                "content": [
+                    {"type": "text", "text": "Describe this image"},
+                    {"type": "image_url", "image_url": {"url": "data:image/png;base64,abc123"}},
+                ],
+            },
+            {"role": "assistant", "content": "I see a cat."},
+        ]
+
+        agent._persist_session(messages, [])
+
+        # The override text should replace the text block, but image blocks
+        # must be preserved.
+        content = messages[0]["content"]
+        assert isinstance(content, list), "Content must remain a list"
+        text_blocks = [b for b in content if isinstance(b, dict) and b.get("type") == "text"]
+        image_blocks = [b for b in content if isinstance(b, dict) and b.get("type") == "image_url"]
+        assert len(text_blocks) == 1
+        assert text_blocks[0]["text"] == "Describe this image"
+        assert len(image_blocks) == 1, "Image block must survive persist override"
+
+    def test_persist_session_preserves_image_blocks_no_text(self, agent):
+        """Multimodal with no text block gets override prepended (fixes #44242)."""
+        agent._session_db = MagicMock()
+        agent.session_id = "session-123"
+        agent._last_flushed_db_idx = 0
+        agent._persist_user_message_idx = 0
+        agent._persist_user_message_override = "Analyze this"
+        messages = [
+            {
+                "role": "user",
+                "content": [
+                    {"type": "image_url", "image_url": {"url": "data:image/png;base64,abc123"}},
+                ],
+            },
+            {"role": "assistant", "content": "I see a cat."},
+        ]
+
+        agent._persist_session(messages, [])
+
+        content = messages[0]["content"]
+        assert isinstance(content, list), "Content must remain a list"
+        assert content[0]["type"] == "text"
+        assert content[0]["text"] == "Analyze this"
+        assert content[1]["type"] == "image_url"
+
 
 class TestReasoningReplayForStrictProviders:
     """Assistant replay must preserve provider-native reasoning fields."""