diff --git a/python/packages/core/agent_framework/_types.py b/python/packages/core/agent_framework/_types.py
index 5199964d92..7481d13e13 100644
--- a/python/packages/core/agent_framework/_types.py
+++ b/python/packages/core/agent_framework/_types.py
@@ -589,10 +589,10 @@ def __init__(
         self.consent_link = consent_link
 
     def __deepcopy__(self, memo: dict[int, Any]) -> Content:
-        """Create a deep copy, preserving ``_SHALLOW_COPY_FIELDS`` by reference.
+        """Create a deep copy, discarding non-``None`` ``_SHALLOW_COPY_FIELDS``.
 
         Fields listed in ``_SHALLOW_COPY_FIELDS`` may contain LLM SDK objects
-        (e.g., proto/gRPC responses) that are not safe to deep-copy.
+        (e.g., proto/gRPC responses) that are not safe to deep-copy or share.
         """
         cls = type(self)
         result = cls.__new__(cls)
@@ -600,7 +600,9 @@ def __deepcopy__(self, memo: dict[int, Any]) -> Content:
         shallow = cls._SHALLOW_COPY_FIELDS
         for k, v in self.__dict__.items():
             if k in shallow:
-                object.__setattr__(result, k, v)
+                if v is not None:
+                    logger.debug("Discarding field '%s' while deep-copying Content.", k)
+                object.__setattr__(result, k, None)
             else:
                 object.__setattr__(result, k, deepcopy(v, memo))
         return result
diff --git a/python/packages/core/tests/core/test_types.py b/python/packages/core/tests/core/test_types.py
index a873b48ae3..23902d17b9 100644
--- a/python/packages/core/tests/core/test_types.py
+++ b/python/packages/core/tests/core/test_types.py
@@ -1197,7 +1197,7 @@ def test_chat_response_updates_to_chat_response_multiple_multiple():
     assert len(chat_response.messages) == 1
     assert isinstance(chat_response.messages[0], Message)
     assert chat_response.messages[0].message_id == "1"
-    assert chat_response.messages[0].contents[0].raw_representation is not None
+    assert chat_response.messages[0].contents[0].raw_representation is None
 
     assert len(chat_response.messages[0].contents) == 3
     assert chat_response.messages[0].contents[0].type == "text"
@@ -1796,17 +1796,17 @@ def test_response_update_propagates_fields_and_metadata():
     assert resp.messages[0].message_id == "mid"
 
 
-def test_text_coalescing_preserves_first_properties():
+def test_text_coalescing_preserves_first_serializable_properties():
     t1 = Content.from_text("A", raw_representation={"r": 1}, additional_properties={"p": 1})
     t2 = Content.from_text("B")
     upd1 = ChatResponseUpdate(contents=[t1], message_id="x")
     upd2 = ChatResponseUpdate(contents=[t2], message_id="x")
     resp = ChatResponse.from_updates([upd1, upd2])
-    # After coalescing there should be a single TextContent with merged text and preserved props from first
+    # After coalescing there should be a single TextContent with merged text and serializable props from first.
     items = [c for c in resp.messages[0].contents if c.type == "text"]
     assert len(items) >= 1
     assert items[0].text == "AB"
-    assert items[0].raw_representation == {"r": 1}
+    assert items[0].raw_representation is None
     assert items[0].additional_properties == {"p": 1}
 
 
@@ -2500,18 +2500,20 @@ def __deepcopy__(self, memo: dict) -> Any:
         raise TypeError("Cannot deepcopy this object")
 
 
-def test_content_deepcopy_preserves_raw_representation():
-    """Test that deepcopy of Content keeps raw_representation by reference."""
+def test_content_deepcopy_discards_raw_representation(caplog: pytest.LogCaptureFixture) -> None:
+    """Test that deepcopy of Content discards raw_representation and logs at debug level."""
     import copy
 
     raw = _NonCopyableRaw()
     content = Content.from_text("hello", raw_representation=raw)
 
-    cloned = copy.deepcopy(content)
+    with caplog.at_level("DEBUG", logger="agent_framework"):
+        cloned = copy.deepcopy(content)
 
     assert cloned.text == "hello"
-    assert cloned.raw_representation is raw
+    assert cloned.raw_representation is None
     assert cloned.additional_properties is not content.additional_properties
+    assert caplog.messages == ["Discarding field 'raw_representation' while deep-copying Content."]
 
 
 def test_message_deepcopy_preserves_raw_representation():
@@ -2617,21 +2619,20 @@ def test_nested_deepcopy_preserves_raw_representation():
     assert cloned.text == "hello"
 
 
-def test_content_deepcopy_shallow_copy_fields_identity():
-    """Test that Content._SHALLOW_COPY_FIELDS fields are identity-preserved while others are deep-copied."""
+def test_content_deepcopy_does_not_log_for_empty_shallow_copy_fields(caplog: pytest.LogCaptureFixture) -> None:
+    """Test that empty shallow-copy fields do not emit discard logs."""
     import copy
 
-    raw = _NonCopyableRaw()
-    content = Content.from_text("hello", raw_representation=raw)
+    content = Content.from_text("hello")
     content.additional_properties["key"] = "value"
 
-    cloned = copy.deepcopy(content)
+    with caplog.at_level("DEBUG", logger="agent_framework"):
+        cloned = copy.deepcopy(content)
 
-    # _SHALLOW_COPY_FIELDS (raw_representation) should be same object
-    assert cloned.raw_representation is raw
-    # Non-shallow fields should be independent deep copies
+    assert cloned.raw_representation is None
     assert cloned.additional_properties is not content.additional_properties
     assert cloned.additional_properties == {"key": "value"}
+    assert caplog.messages == []
 
 
 def test_chat_response_deepcopy_deep_copies_additional_properties():