fix(agents): avoid invalid message order after summarize (#9260)

Co-authored-by: Christian Bromann <[email protected]>

Author: crishoj

.changeset/fancy-breads-allow.md

@@ -0,0 +1,5 @@
+---
+"langchain": patch
+---
+
+avoid invalid message order after summarization

libs/langchain/src/agents/middleware/summarization.ts

@@ -316,6 +316,15 @@ function isSafeCutoffPoint(
     return true;
   }
 
+  // Prevent preserved messages from starting with AI message containing tool calls
+  if (
+    cutoffIndex < messages.length &&
+    AIMessage.isInstance(messages[cutoffIndex]) &&
+    hasToolCalls(messages[cutoffIndex])
+  ) {
+    return false;
+  }
+
   const searchStart = Math.max(0, cutoffIndex - SEARCH_RANGE_FOR_TOOL_PAIRS);
   const searchEnd = Math.min(
     messages.length,

libs/langchain/src/agents/middleware/tests/summarization.test.ts

@@ -10,6 +10,7 @@ import {
 import { summarizationMiddleware } from "../summarization.js";
 import { countTokensApproximately } from "../utils.js";
 import { createAgent } from "../../index.js";
+import { hasToolCalls } from "../../utils.js";
 import { FakeToolCallingChatModel } from "../../tests/utils.js";
 
 // Mock @langchain/anthropic to test model string usage without requiring the built package
@@ -379,8 +380,67 @@ describe("summarizationMiddleware", () => {
       model,
       middleware: [middleware],
     });
-
     const result = await agent.invoke({ messages: [] });
     expect(result.messages.at(-1)?.content).toBe("Mocked response");
   });
+
+  it("should not start preserved messages with AI message containing tool calls", async () => {
+    const summarizationModel = createMockSummarizationModel();
+    const model = createMockMainModel();
+
+    const middleware = summarizationMiddleware({
+      model: summarizationModel as any,
+      maxTokensBeforeSummary: 50, // Very low threshold to trigger summarization
+      messagesToKeep: 2, // Keep very few messages to force problematic cutoff
+    });
+
+    const agent = createAgent({
+      model,
+      middleware: [middleware],
+    });
+
+    // Create a conversation history that would cause the problematic scenario
+    // We need messages where an AI message with tool calls would be the first preserved message
+    // after summarization if the cutoff isn't adjusted properly
+    const messages = [
+      new HumanMessage(
+        `First message with some content to take up tokens. ${"x".repeat(100)}`
+      ),
+      new AIMessage(`First response. ${"x".repeat(100)}`),
+      new HumanMessage(
+        `Second message with more content to build up tokens. ${"x".repeat(
+          100
+        )}`
+      ),
+      new AIMessage(`Second response. ${"x".repeat(100)}`),
+      // This AI message with tool calls should NOT be the first preserved message
+      new AIMessage({
+        content: "Let me search for information.",
+        tool_calls: [{ id: "call_1", name: "search", args: { query: "test" } }],
+      }),
+      new ToolMessage({
+        content: "Search results",
+        tool_call_id: "call_1",
+      }),
+      new HumanMessage("What did you find?"),
+    ];
+
+    const result = await agent.invoke({ messages });
+
+    // Verify summarization occurred
+    expect(result.messages[0]).toBeInstanceOf(SystemMessage);
+    const systemPrompt = result.messages[0] as SystemMessage;
+    expect(systemPrompt.content).toContain("## Previous conversation summary:");
+
+    // Verify preserved messages don't start with AI(tool calls)
+    const preservedMessages = result.messages.filter(
+      (m) => !SystemMessage.isInstance(m)
+    );
+    expect(preservedMessages.length).toBeGreaterThan(0);
+    const firstPreserved = preservedMessages[0];
+    // The first preserved message should not be an AI message with tool calls
+    expect(
+      !(AIMessage.isInstance(firstPreserved) && hasToolCalls(firstPreserved))
+    ).toBe(true);
+  });
 });