diff --git a/litellm/harness/handlers/tool_loop_handler.py b/litellm/harness/handlers/tool_loop_handler.py
index dda353263d8..f7fcd50a05d 100644
--- a/litellm/harness/handlers/tool_loop_handler.py
+++ b/litellm/harness/handlers/tool_loop_handler.py
@@ -398,11 +398,11 @@ class ToolLoopHandler(BaseHarnessHandler):
                     parse_error,
                     approval_error,
                 )
-                yield ToolResult(id=call.id, output=outcome.output, is_error=outcome.is_error)
                 tool_message: ChatCompletionMessageParam = {
                     "role": "tool",
                     "tool_call_id": call.id,
                     "content": outcome.output,
                 }
                 self._messages = (*self._messages, tool_message)
+                yield ToolResult(id=call.id, output=outcome.output, is_error=outcome.is_error)
         raise HarnessTurnError(f"Harness.TOOL_LOOP exceeded {TOOL_LOOP_MAX_MODEL_CALLS} model calls in one turn")
diff --git a/litellm/llms/tool_loop/harness/transformation.py b/litellm/llms/tool_loop/harness/transformation.py
index 3a4ab6eb304..9a6483f8af5 100644
--- a/litellm/llms/tool_loop/harness/transformation.py
+++ b/litellm/llms/tool_loop/harness/transformation.py
@@ -78,9 +78,11 @@ def _routing_kwargs(ctx: SessionContext, options: ToolLoopOptions) -> Mapping[st
         raise ValueError("Harness.TOOL_LOOP needs model=")
     if ctx.gateway is not None:
         caller_headers_value: Final[object] = _OBJECT_ADAPTER.validate_python(
-            options.completion_kwargs.get("extra_headers", {})
+            options.completion_kwargs.get("extra_headers")
+        )
+        caller_headers: Final = _STRING_HEADERS_ADAPTER.validate_python(
+            MappingProxyType({}) if caller_headers_value is None else caller_headers_value
         )
-        caller_headers: Final = _STRING_HEADERS_ADAPTER.validate_python(caller_headers_value)
         extra_headers: Final[dict[str, str]] = {  # mutable-ok: acompletion(extra_headers=) requires a dict
             **caller_headers,
             **gateway_headers(ctx),
diff --git a/tests/unit/harness/handlers/test_tool_loop_handler.py b/tests/unit/harness/handlers/test_tool_loop_handler.py
index df1e56404a0..7fff40015f6 100644
--- a/tests/unit/harness/handlers/test_tool_loop_handler.py
+++ b/tests/unit/harness/handlers/test_tool_loop_handler.py
@@ -2,9 +2,9 @@
 
 from __future__ import annotations
 
-from collections.abc import Callable, Iterator, Mapping
+from collections.abc import AsyncGenerator, Callable, Iterator, Mapping
 from pathlib import Path
-from typing import Final, Literal
+from typing import Final, Literal, cast
 
 import pytest
 from pydantic import BaseModel
@@ -556,6 +556,52 @@ async def test_interrupted_tool_calls_are_closed_before_the_next_session_turn(tm
     ]
 
 
+async def test_closing_after_tool_result_keeps_result_and_interrupts_remaining_call(tmp_path: Path) -> None:
+    executed: list[str] = []  # mutable-ok: records which injected tools ran
+
+    def first_tool() -> str:
+        executed.append("first")
+        return "first result"
+
+    def second_tool() -> str:
+        executed.append("second")
+        return "second result"
+
+    completion: Final = ScriptedCompletion(
+        (
+            model_response(
+                tool_calls=(
+                    function_call("first_tool", "{}", "call-1"),
+                    function_call("second_tool", "{}", "call-2"),
+                )
+            ),
+        )
+    )
+    ctx: Final = make_context(tmp_path, tools=(first_tool, second_tool))
+    handler: Final = make_handler(completion)
+    await handler.start(ctx)
+
+    turn: Final = cast(AsyncGenerator[Event, None], handler.turn(ctx, "first turn"))
+    tool_results: list[ToolResult] = []  # mutable-ok: records the first yielded tool result
+    async for event in turn:
+        if isinstance(event, ToolResult):
+            tool_results.append(event)
+            break
+    await turn.aclose()
+    await handler.stop(ctx)
+
+    assert tool_results == [ToolResult(id="call-1", output="first result", is_error=False)]
+    assert executed == ["first"]
+    assert (await handler.history(ctx))[-2:] == [
+        {"role": "tool", "tool_call_id": "call-1", "content": "first result"},
+        {
+            "role": "tool",
+            "tool_call_id": "call-2",
+            "content": "interrupted: the turn ended before this tool ran",
+        },
+    ]
+
+
 async def test_duplicate_tool_names_are_rejected(tmp_path: Path) -> None:
     ctx: Final = make_context(tmp_path, tools=(add, duplicate_add()))
     handler: Final = make_handler(ScriptedCompletion(()))
diff --git a/tests/unit/llms/tool_loop/harness/test_transformation.py b/tests/unit/llms/tool_loop/harness/test_transformation.py
index 68cfdf44a8d..8dc9a8f07f5 100644
--- a/tests/unit/llms/tool_loop/harness/test_transformation.py
+++ b/tests/unit/llms/tool_loop/harness/test_transformation.py
@@ -161,6 +161,19 @@ def test_gateway_extra_headers_must_be_string_mappings(tmp_path: Path) -> None:
         completion_kwargs(ctx)
 
 
+def test_gateway_none_extra_headers_uses_only_gateway_headers(tmp_path: Path) -> None:
+    gateway: Final = GatewayTarget(api_base="https://gateway", api_key="virtual-key")
+    ctx: Final = make_context(
+        tmp_path,
+        gateway=gateway,
+        options=ToolLoopOptions(completion_kwargs={"extra_headers": None}),
+    )
+
+    kwargs: Final = completion_kwargs(ctx)
+
+    assert kwargs["extra_headers"] == {"x-litellm-tags": "harness,tool_loop"}
+
+
 def test_configuration_requires_model_and_declares_capabilities(tmp_path: Path) -> None:
     config: Final = ToolLoopHarnessConfig()
     assert config.uses_model_endpoint is False