diff --git a/agent/title_generator.py b/agent/title_generator.py
index f2ac6c9f1a35e..cb8b662fa442e 100644
--- a/agent/title_generator.py
+++ b/agent/title_generator.py
@@ -21,10 +21,11 @@ import json
 import logging
 import re
 import threading
-from typing import Callable, Optional
+from typing import Any, Callable, Optional
 
 from agent.auxiliary_client import call_llm
 from agent.context_compressor import LEGACY_SUMMARY_PREFIX
+from agent.message_content import flatten_message_text
 
 logger = logging.getLogger(__name__)
 
@@ -632,6 +633,27 @@ def _auto_title_session(
         logger.debug("Failed to set auto-generated title: %s", e)
 
 
+def _is_real_user_turn(message: Any) -> bool:
+    """Whether a history entry is a question a person actually asked.
+
+    Hermes persists a lot of machinery under ``role="user"`` — compaction
+    handoffs, model-switch markers, background-process notices — because strict
+    OpenAI-compatible providers reject a system message that isn't first.
+    Counting those as turns is what made a session that merely *opened* with one
+    look like it was already past the point where titling applies.
+
+    A multimodal turn is judged on its text, so "here's a screenshot, fix the
+    login" counts as the real question it is.
+    """
+    if not isinstance(message, dict) or message.get("role") != "user":
+        return False
+    content = message.get("content")
+
+    return is_titleable_user_message(
+        content if isinstance(content, str) else flatten_message_text(content)
+    )
+
+
 def _session_is_untitled(session_db, session_id: str) -> bool:
     """Whether the session still carries no title of any provenance.
 
@@ -677,25 +699,17 @@ def maybe_auto_title(
     if not session_db or not session_id or not user_message:
         return
 
-    # Count user messages to detect the opening turn. ``conversation_history``
-    # is the state BEFORE this turn's message is appended when called from the
-    # turn prologue, and after it when called post-response, so accept both.
-    # Entries are dicts; anything else means a caller passed the wrong
-    # positional and titling must degrade quietly rather than raise.
+    # Count the real questions behind us to detect the opening turn.
+    # ``conversation_history`` is the state BEFORE this turn's message is
+    # appended when called from the turn prologue, and after it when called
+    # post-response, so accept both.
     #
-    # Machine-authored openers are excluded from the count. They are persisted
-    # with role="user" (see _MACHINE_PREFIXES), so counting them would make a
-    # session that opened with e.g. a model-switch marker look like it was
-    # already past its opening turn — the real first question then arrives at
-    # count 2 and never gets titled at all, leaving the session permanently
-    # NULL-titled.
-    user_msg_count = sum(
-        1
-        for m in (conversation_history or [])
-        if isinstance(m, dict)
-        and m.get("role") == "user"
-        and is_titleable_user_message(m.get("content") or "")
-    )
+    # Two things have to be true to skip: we are past the opening turn AND the
+    # session already has a name. Either alone gets it wrong. The count alone
+    # left a session that opened with machinery permanently nameless, because
+    # nothing reconsidered it. The title alone would never title at all on a
+    # store too old to report one.
+    user_msg_count = sum(1 for m in (conversation_history or []) if _is_real_user_turn(m))
     if user_msg_count > 1 and not _session_is_untitled(session_db, session_id):
         return
 
diff --git a/tests/agent/test_title_generator.py b/tests/agent/test_title_generator.py
index 72c70fa6ed212..56190980b7b71 100644
--- a/tests/agent/test_title_generator.py
+++ b/tests/agent/test_title_generator.py
@@ -296,6 +296,29 @@ class TestMaybeAutoTitle:
         assert db.get_session_title("sess-1") is None
         mock_auto.assert_not_called()
 
+    def test_a_multimodal_turn_counts_as_a_real_question(self, tmp_path):
+        """"Here's a screenshot, fix the login" is a question, parts list or not.
+
+        Judging a turn by `content` alone reads a multimodal one as machinery
+        and undercounts the conversation, so a session deep into its history
+        looks like it is still on its opening turn.
+        """
+        from agent.title_generator import _is_real_user_turn
+
+        assert _is_real_user_turn(
+            {
+                "role": "user",
+                "content": [
+                    {"type": "image_url", "image_url": {"url": "data:image/png;base64,x"}},
+                    {"type": "text", "text": "fix the login button"},
+                ],
+            }
+        )
+        # An image with no words is not a question we can name anything after.
+        assert not _is_real_user_turn(
+            {"role": "user", "content": [{"type": "image_url", "image_url": {"url": "x"}}]}
+        )
+
     def test_titles_on_a_later_turn_when_the_opener_was_not_titleable(self, tmp_path):
         """A session whose opener couldn't be titled gets named by a later turn.