diff --git a/apps/agentstack-server/src/agentstack_server/configuration.py b/apps/agentstack-server/src/agentstack_server/configuration.py
index 6434b1901..36e0f0d5a 100644
--- a/apps/agentstack-server/src/agentstack_server/configuration.py
+++ b/apps/agentstack-server/src/agentstack_server/configuration.py
@@ -310,6 +310,11 @@ class GenerateConversationTitleConfiguration(BaseModel):
 
         CONVERSATION CONTENT:
         ```
+        {% if titleHint %}
+        Title hint:
+        {{ titleHint }}
+        {% endif %}
+
         User message:
         {{ text }}
 
diff --git a/apps/agentstack-server/src/agentstack_server/infrastructure/persistence/repositories/context.py b/apps/agentstack-server/src/agentstack_server/infrastructure/persistence/repositories/context.py
index 457dc520f..1d9d60161 100644
--- a/apps/agentstack-server/src/agentstack_server/infrastructure/persistence/repositories/context.py
+++ b/apps/agentstack-server/src/agentstack_server/infrastructure/persistence/repositories/context.py
@@ -165,7 +165,8 @@ async def update_title(
         self, *, context_id: UUID, title: str | None = None, generation_state: TitleGenerationState
     ) -> None:
         # validate length before saving to database
-        _ = TypeAdapter(Metadata).validate_python({"title": title})
+        if title:
+            _ = TypeAdapter(Metadata).validate_python({"title": title})
         context = await self.get(context_id=context_id)
         query = (
             contexts_table.update()
diff --git a/apps/agentstack-server/src/agentstack_server/service_layer/services/contexts.py b/apps/agentstack-server/src/agentstack_server/service_layer/services/contexts.py
index 592ce636f..4dc1fdc71 100644
--- a/apps/agentstack-server/src/agentstack_server/service_layer/services/contexts.py
+++ b/apps/agentstack-server/src/agentstack_server/service_layer/services/contexts.py
@@ -7,7 +7,7 @@
 from datetime import timedelta
 from uuid import UUID
 
-from a2a.types import Artifact, FilePart, FileWithBytes, FileWithUri, Message, Role, TextPart
+from a2a.types import Artifact, DataPart, FilePart, FileWithBytes, FileWithUri, Message, Role, TextPart
 from fastapi import status
 from kink import inject
 from pydantic import TypeAdapter
@@ -155,10 +155,23 @@ async def update_last_active(self, *, context_id: UUID) -> None:
             await uow.contexts.update_last_active(context_id=context_id)
             await uow.commit()
 
-    def _extract_content_for_title(self, msg: Message | Artifact) -> tuple[str, Sequence[FileWithUri | FileWithBytes]]:
-        text_parts = [part.root.text for part in msg.parts if isinstance(part.root, TextPart)]
-        files = [part.root.file for part in msg.parts if isinstance(part.root, FilePart)]
-        return "".join(text_parts), files
+    def _extract_content_for_title(
+        self, msg: Message | Artifact
+    ) -> tuple[str, str | None, Sequence[FileWithUri | FileWithBytes]]:
+        title_hint: str | None = None
+        text_parts: list[str] = []
+        files: list[FileWithUri | FileWithBytes] = []
+        for part in msg.parts:
+            match part.root:
+                case TextPart(text=text):
+                    text_parts.append(text)
+                case DataPart(data={"title_hint": str(hint)}) if hint and not title_hint:
+                    title_hint = hint
+                case FilePart(file=file):
+                    files.append(file)
+                case _:
+                    pass
+        return "".join(text_parts), title_hint, files
 
     async def add_history_item(self, *, context_id: UUID, data: ContextHistoryItemData, user: User) -> None:
         async with self._uow() as uow:
@@ -202,8 +215,9 @@ async def generate_conversation_title(self, *, context_id: UUID):
             logger.warning(f"Cannot generate title for context {context_id}: no history found.")
             return
 
-        text, files = self._extract_content_for_title(msg.items[0].data)
-        if not text and not files:
+        raw_message = msg.items[0].data
+        text, title_hint, files = self._extract_content_for_title(raw_message)
+        if not text and not title_hint and not files:
             logger.warning(f"Cannot generate title for context {context_id}: first message has no content.")
             return
 
@@ -212,7 +226,9 @@ async def generate_conversation_title(self, *, context_id: UUID):
             template = Template(self._configuration.generate_conversation_title.prompt)
             prompt = template.render(
                 text=text,
+                titleHint=title_hint,
                 files=[file.model_dump(include={"name", "mime_type"}) for file in files],
+                rawMessage=raw_message.model_dump(),
             )
             resp = await self._model_provider_service.create_chat_completion(
                 request=ChatCompletionRequest(
@@ -222,8 +238,10 @@ async def generate_conversation_title(self, *, context_id: UUID):
                     messages=[{"role": "user", "content": prompt}],
                 )
             )
-            title = resp["choices"][0]["message"]["content"].strip().strip("\"'")  # pyright: ignore [reportIndexIssue]
+            title = (resp.choices[0].message.content or "").strip().strip("\"'")
             title = f"{title[:100]}..." if len(title) > 100 else title
+            if not title:
+                raise RuntimeError("Generated title is empty.")
             async with self._uow() as uow:
                 await uow.contexts.update_title(
                     context_id=context_id, title=title, generation_state=TitleGenerationState.COMPLETED
diff --git a/helm/values.yaml b/helm/values.yaml
index ff6e8bee0..d4da853c4 100644
--- a/helm/values.yaml
+++ b/helm/values.yaml
@@ -23,6 +23,12 @@ a2aProxyRequestsExpireAfterDays: 14
 generateConversationTitle:
   enabled: true
   model: default
+  # You can use the following variables in prompt:
+  # - text: all text parts of the user message concatenated
+  # - files: list of files attached to the user message
+  # - titleHint: hint for the title extracted from DataPart
+  # - rawMessage: entire user message object, WARNING: may contain secrets in metadata, be careful not to send them to the LLM
+  
   prompt: |
     YOUR INSTRUCTIONS:
     Write a short descriptive title for the conversation (max 100 characters).
@@ -34,6 +40,11 @@ generateConversationTitle:
 
     CONVERSATION CONTENT:
     ```
+    {% if titleHint %}
+    Title hint:
+    {{ titleHint }}
+    {% endif %}
+
     User message:
     {{ text }}