diff --git a/python/packages/a2a/agent_framework_a2a/_agent.py b/python/packages/a2a/agent_framework_a2a/_agent.py
index a07be3cf2f..696a160cf6 100644
--- a/python/packages/a2a/agent_framework_a2a/_agent.py
+++ b/python/packages/a2a/agent_framework_a2a/_agent.py
@@ -295,7 +295,10 @@ def run(  # pyright: ignore[reportIncompatibleMethodOverride]
         else:
             if not normalized_messages:
                 raise ValueError("At least one message is required when starting a new task (no continuation_token).")
-            a2a_message = self._prepare_message_for_a2a(normalized_messages[-1])
+            a2a_message = self._prepare_message_for_a2a(
+                normalized_messages[-1],
+                context_id=session.service_session_id if session else None,
+            )
             a2a_stream = self.client.send_message(a2a_message)
 
         provider_session = session
@@ -584,7 +587,7 @@ async def poll_task(self, continuation_token: A2AContinuationToken) -> AgentResp
             return AgentResponse.from_updates(updates)
         return AgentResponse(messages=[], response_id=task.id, raw_representation=task)
 
-    def _prepare_message_for_a2a(self, message: Message) -> A2AMessage:
+    def _prepare_message_for_a2a(self, message: Message, *, context_id: str | None = None) -> A2AMessage:
         """Prepare a Message for the A2A protocol.
 
         Transforms Agent Framework Message objects into A2A protocol Messages by:
@@ -593,6 +596,13 @@ def _prepare_message_for_a2a(self, message: Message) -> A2AMessage:
         - Converting file references (URI/data/hosted_file) to FilePart objects
         - Preserving metadata and additional properties from the original message
         - Setting the role to 'user' as framework messages are treated as user input
+
+        Args:
+            message: The framework Message to convert.
+            context_id: Optional fallback context identifier (e.g. derived from
+                ``AgentSession.service_session_id``). When the *message* already
+                carries a ``context_id`` in its ``additional_properties`` that
+                value takes precedence; otherwise this fallback is used.
         """
         parts: list[A2APart] = []
         if not message.contents:
@@ -672,7 +682,7 @@ def _prepare_message_for_a2a(self, message: Message) -> A2AMessage:
             role=A2ARole("user"),
             parts=parts,
             message_id=message.message_id or uuid.uuid4().hex,
-            context_id=message.additional_properties.get("context_id"),
+            context_id=message.additional_properties.get("context_id") or context_id,
             metadata=metadata,
         )
 
diff --git a/python/packages/a2a/tests/test_a2a_agent.py b/python/packages/a2a/tests/test_a2a_agent.py
index 484d71e22c..dbbad8a865 100644
--- a/python/packages/a2a/tests/test_a2a_agent.py
+++ b/python/packages/a2a/tests/test_a2a_agent.py
@@ -46,6 +46,7 @@ def __init__(self) -> None:
         self.responses: list[Any] = []
         self.resubscribe_responses: list[Any] = []
         self.get_task_response: Task | None = None
+        self.last_message: Any = None
 
     def add_message_response(self, message_id: str, text: str, role: str = "agent") -> None:
         """Add a mock Message response."""
@@ -111,6 +112,7 @@ def add_in_progress_task_response(
 
     async def send_message(self, message: Any) -> AsyncIterator[Any]:
         """Mock send_message method that yields responses."""
+        self.last_message = message
         self.call_count += 1
 
         # All queued responses are delivered as a single streaming batch per call.
@@ -539,6 +541,37 @@ def test_prepare_message_for_a2a_forwards_context_id() -> None:
     assert result.metadata == {"trace_id": "trace-456"}
 
 
+def test_prepare_message_for_a2a_uses_fallback_context_id() -> None:
+    """Test that context_id kwarg is used when message has no context_id property."""
+
+    agent = A2AAgent(client=MagicMock(), http_client=None)
+
+    message = Message(
+        role="user",
+        contents=[Content.from_text(text="Hello")],
+    )
+
+    result = agent._prepare_message_for_a2a(message, context_id="session-ctx-1")
+
+    assert result.context_id == "session-ctx-1"
+
+
+def test_prepare_message_for_a2a_message_context_id_takes_precedence() -> None:
+    """Test that message.additional_properties context_id wins over the fallback."""
+
+    agent = A2AAgent(client=MagicMock(), http_client=None)
+
+    message = Message(
+        role="user",
+        contents=[Content.from_text(text="Hello")],
+        additional_properties={"context_id": "explicit-ctx"},
+    )
+
+    result = agent._prepare_message_for_a2a(message, context_id="session-ctx-1")
+
+    assert result.context_id == "explicit-ctx"
+
+
 def test_parse_contents_from_a2a_with_data_part() -> None:
     """Test conversion of A2A DataPart."""
 
@@ -868,6 +901,43 @@ async def test_poll_task_completed(a2a_agent: A2AAgent, mock_a2a_client: MockA2A
 # endregion
 
 
+# region Session context_id Integration Tests
+
+
+@mark.asyncio
+async def test_run_passes_session_service_session_id_as_context_id(mock_a2a_client: MockA2AClient) -> None:
+    """Test that run() wires session.service_session_id to the A2A message context_id."""
+    agent = A2AAgent(name="Test Agent", id="test-agent", client=mock_a2a_client, http_client=None)
+    mock_a2a_client.add_message_response("msg-ctx", "reply")
+
+    session = AgentSession(service_session_id="svc-session-42")
+    await agent.run("Hello", session=session)
+
+    assert mock_a2a_client.last_message is not None
+    assert mock_a2a_client.last_message.context_id == "svc-session-42"
+
+
+@mark.asyncio
+async def test_run_message_context_id_takes_precedence_over_session(mock_a2a_client: MockA2AClient) -> None:
+    """Test that an explicit context_id on the message wins over session.service_session_id."""
+    agent = A2AAgent(name="Test Agent", id="test-agent", client=mock_a2a_client, http_client=None)
+    mock_a2a_client.add_message_response("msg-ctx2", "reply")
+
+    session = AgentSession(service_session_id="svc-session-42")
+    message = Message(
+        role="user",
+        contents=[Content.from_text(text="Hello")],
+        additional_properties={"context_id": "explicit-ctx"},
+    )
+    await agent.run(messages=[message], session=session)
+
+    assert mock_a2a_client.last_message is not None
+    assert mock_a2a_client.last_message.context_id == "explicit-ctx"
+
+
+# endregion
+
+
 # region Context Provider Tests
 
 
diff --git a/python/samples/02-agents/conversations/file_history_provider.py b/python/samples/02-agents/conversations/file_history_provider.py
index 04a87f8224..20735ffd17 100644
--- a/python/samples/02-agents/conversations/file_history_provider.py
+++ b/python/samples/02-agents/conversations/file_history_provider.py
@@ -21,7 +21,7 @@
 from pydantic import Field
 
 try:
-    import orjson
+    import orjson  # pyright: ignore[reportMissingImports]
 except ImportError:
     orjson = None
 
diff --git a/python/samples/02-agents/conversations/file_history_provider_conversation_persistence.py b/python/samples/02-agents/conversations/file_history_provider_conversation_persistence.py
index 70c5d7e8e8..693501b0f9 100644
--- a/python/samples/02-agents/conversations/file_history_provider_conversation_persistence.py
+++ b/python/samples/02-agents/conversations/file_history_provider_conversation_persistence.py
@@ -22,7 +22,7 @@
 from pydantic import Field
 
 try:
-    import orjson
+    import orjson  # pyright: ignore[reportMissingImports]
 except ImportError:
     orjson = None