diff --git a/libs/langchain_v1/langchain/agents/middleware/human_in_the_loop.py b/libs/langchain_v1/langchain/agents/middleware/human_in_the_loop.py
index a29b23e7ec620..a547e2ce95576 100644
--- a/libs/langchain_v1/langchain/agents/middleware/human_in_the_loop.py
+++ b/libs/langchain_v1/langchain/agents/middleware/human_in_the_loop.py
@@ -2,7 +2,8 @@
 
 from typing import Any, Literal, Protocol
 
-from langchain_core.messages import AIMessage, ToolCall, ToolMessage
+from langchain_core.messages import AIMessage, RemoveMessage, ToolCall, ToolMessage
+from langgraph.graph.message import REMOVE_ALL_MESSAGES
 from langgraph.runtime import Runtime
 from langgraph.types import interrupt
 from typing_extensions import NotRequired, TypedDict
@@ -269,6 +270,42 @@ def _process_decision(
         )
         raise ValueError(msg)
 
+    def before_agent(self, state: AgentState, runtime: Runtime) -> dict[str, Any] | None:  # noqa: ARG002
+        """Before the agent runs, handle dangling tool calls from the most recent AIMessage."""
+        messages = state["messages"]
+        if not messages or len(messages) == 0:
+            return None
+
+        patched_messages = []
+        # Iterate over the messages and add any dangling tool calls
+        for i, msg in enumerate(messages):
+            patched_messages.append(msg)
+            if msg.type == "ai" and msg.tool_calls:
+                for tool_call in msg.tool_calls:
+                    corresponding_tool_msg = next(
+                        (
+                            msg
+                            for msg in messages[i:]
+                            if msg.type == "tool" and msg.tool_call_id == tool_call["id"]
+                        ),
+                        None,
+                    )
+                    if corresponding_tool_msg is None:
+                        # We have a dangling tool call which needs a ToolMessage
+                        tool_msg = (
+                            f"Tool call {tool_call['name']} with id {tool_call['id']} was "
+                            "cancelled - another message came in before it could be completed."
+                        )
+                        patched_messages.append(
+                            ToolMessage(
+                                content=tool_msg,
+                                name=tool_call["name"],
+                                tool_call_id=tool_call["id"],
+                            )
+                        )
+
+        return {"messages": [RemoveMessage(id=REMOVE_ALL_MESSAGES), *patched_messages]}
+
     def after_model(self, state: AgentState, runtime: Runtime) -> dict[str, Any] | None:
         """Trigger interrupt flows for relevant tool calls after an AIMessage."""
         messages = state["messages"]
diff --git a/libs/langchain_v1/tests/unit_tests/agents/middleware/test_hitl.py b/libs/langchain_v1/tests/unit_tests/agents/middleware/test_hitl.py
new file mode 100644
index 0000000000000..1ed99af26252b
--- /dev/null
+++ b/libs/langchain_v1/tests/unit_tests/agents/middleware/test_hitl.py
@@ -0,0 +1,142 @@
+from langchain.agents.middleware.human_in_the_loop import HumanInTheLoopMiddleware
+from langchain_core.messages import (
+    SystemMessage,
+    HumanMessage,
+    AIMessage,
+    ToolMessage,
+    ToolCall,
+    RemoveMessage,
+)
+from langgraph.graph.message import add_messages
+
+
+class TestHumanInTheLoopMiddlewareBeforeModel:
+    """Test HumanInTheLoopMiddleware before_model behavior."""
+
+    def test_first_message(self) -> None:
+        input_messages = [
+            SystemMessage(content="You are a helpful assistant.", id="1"),
+            HumanMessage(content="Hello, how are you?", id="2"),
+        ]
+        middleware = HumanInTheLoopMiddleware(interrupt_on={})
+        state_update = middleware.before_agent({"messages": input_messages}, None)
+        assert state_update is not None
+        assert len(state_update["messages"]) == 3
+        assert state_update["messages"][0].type == "remove"
+        assert state_update["messages"][1].type == "system"
+        assert state_update["messages"][1].content == "You are a helpful assistant."
+        assert state_update["messages"][2].type == "human"
+        assert state_update["messages"][2].content == "Hello, how are you?"
+        assert state_update["messages"][2].id == "2"
+
+    def test_missing_tool_call(self) -> None:
+        input_messages = [
+            SystemMessage(content="You are a helpful assistant.", id="1"),
+            HumanMessage(content="Hello, how are you?", id="2"),
+            AIMessage(
+                content="I'm doing well, thank you!",
+                tool_calls=[
+                    ToolCall(id="123", name="get_events_for_days", args={"date_str": "2025-01-01"})
+                ],
+                id="3",
+            ),
+            HumanMessage(content="What is the weather in Tokyo?", id="4"),
+        ]
+        middleware = HumanInTheLoopMiddleware(interrupt_on={})
+        state_update = middleware.before_agent({"messages": input_messages}, None)
+        assert state_update is not None
+        assert len(state_update["messages"]) == 6
+        assert state_update["messages"][0].type == "remove"
+        assert state_update["messages"][1] == input_messages[0]
+        assert state_update["messages"][2] == input_messages[1]
+        assert state_update["messages"][3] == input_messages[2]
+        assert state_update["messages"][4].type == "tool"
+        assert state_update["messages"][4].tool_call_id == "123"
+        assert state_update["messages"][4].name == "get_events_for_days"
+        assert state_update["messages"][5] == input_messages[3]
+        updated_messages = add_messages(input_messages, state_update["messages"])
+        assert len(updated_messages) == 5
+        assert updated_messages[0] == input_messages[0]
+        assert updated_messages[1] == input_messages[1]
+        assert updated_messages[2] == input_messages[2]
+        assert updated_messages[3].type == "tool"
+        assert updated_messages[3].tool_call_id == "123"
+        assert updated_messages[3].name == "get_events_for_days"
+        assert updated_messages[4] == input_messages[3]
+
+    def test_no_missing_tool_calls(self) -> None:
+        input_messages = [
+            SystemMessage(content="You are a helpful assistant.", id="1"),
+            HumanMessage(content="Hello, how are you?", id="2"),
+            AIMessage(
+                content="I'm doing well, thank you!",
+                tool_calls=[
+                    ToolCall(id="123", name="get_events_for_days", args={"date_str": "2025-01-01"})
+                ],
+                id="3",
+            ),
+            ToolMessage(content="I have no events for that date.", tool_call_id="123", id="4"),
+            HumanMessage(content="What is the weather in Tokyo?", id="5"),
+        ]
+        middleware = HumanInTheLoopMiddleware(interrupt_on={})
+        state_update = middleware.before_agent({"messages": input_messages}, None)
+        assert state_update is not None
+        assert len(state_update["messages"]) == 6
+        assert state_update["messages"][0].type == "remove"
+        assert state_update["messages"][1:] == input_messages
+        updated_messages = add_messages(input_messages, state_update["messages"])
+        assert len(updated_messages) == 5
+        assert updated_messages == input_messages
+
+    def test_two_missing_tool_calls(self) -> None:
+        input_messages = [
+            SystemMessage(content="You are a helpful assistant.", id="1"),
+            HumanMessage(content="Hello, how are you?", id="2"),
+            AIMessage(
+                content="I'm doing well, thank you!",
+                tool_calls=[
+                    ToolCall(id="123", name="get_events_for_days", args={"date_str": "2025-01-01"})
+                ],
+                id="3",
+            ),
+            HumanMessage(content="What is the weather in Tokyo?", id="4"),
+            AIMessage(
+                content="I'm doing well, thank you!",
+                tool_calls=[
+                    ToolCall(id="456", name="get_events_for_days", args={"date_str": "2025-01-01"})
+                ],
+                id="5",
+            ),
+            HumanMessage(content="What is the weather in Tokyo?", id="6"),
+        ]
+        middleware = HumanInTheLoopMiddleware(interrupt_on={})
+        state_update = middleware.before_agent({"messages": input_messages}, None)
+        assert state_update is not None
+        assert len(state_update["messages"]) == 9
+        assert state_update["messages"][0].type == "remove"
+        assert state_update["messages"][1] == input_messages[0]
+        assert state_update["messages"][2] == input_messages[1]
+        assert state_update["messages"][3] == input_messages[2]
+        assert state_update["messages"][4].type == "tool"
+        assert state_update["messages"][4].tool_call_id == "123"
+        assert state_update["messages"][4].name == "get_events_for_days"
+        assert state_update["messages"][5] == input_messages[3]
+        assert state_update["messages"][6] == input_messages[4]
+        assert state_update["messages"][7].type == "tool"
+        assert state_update["messages"][7].tool_call_id == "456"
+        assert state_update["messages"][7].name == "get_events_for_days"
+        assert state_update["messages"][8] == input_messages[5]
+        updated_messages = add_messages(input_messages, state_update["messages"])
+        assert len(updated_messages) == 8
+        assert updated_messages[0] == input_messages[0]
+        assert updated_messages[1] == input_messages[1]
+        assert updated_messages[2] == input_messages[2]
+        assert updated_messages[3].type == "tool"
+        assert updated_messages[3].tool_call_id == "123"
+        assert updated_messages[3].name == "get_events_for_days"
+        assert updated_messages[4] == input_messages[3]
+        assert updated_messages[5] == input_messages[4]
+        assert updated_messages[6].type == "tool"
+        assert updated_messages[6].tool_call_id == "456"
+        assert updated_messages[6].name == "get_events_for_days"
+        assert updated_messages[7] == input_messages[5]