[Fix] Anthropic tool_use / tool_result pairing errors (400)

src/core/task/Task.ts

@@ -140,6 +140,7 @@ import { type AutoDenyDetail, AutoApprovalHandler, checkAutoApproval } from "../
 import { MessageManager } from "../message-manager"
 import { validateAndFixToolResultIds } from "./validateToolResultIds"
 import { mergeConsecutiveApiMessages } from "./mergeConsecutiveApiMessages"
+import { normalizeToolResultPairing } from "./normalizeToolResultPairing"
 import { prepareApiConversationMessage } from "./apiConversationHistory"
 import { shouldAddUserMessageToHistory } from "./messageCounting"
 import { type TaskExecutionContext } from "./providerHandoff"
@@ -574,7 +575,8 @@ export class Task extends EventEmitter<TaskEvents> implements TaskLike {
 	}
 
 	/**
-	 * Push a tool_result block to userMessageContent, preventing duplicates.
+	 * Push a tool_result block to userMessageContent after any existing tool_results
+	 * (ahead of images and text), preventing duplicates.
 	 * Duplicate tool_use_ids cause API errors.
 	 *
 	 * @param toolResult - The tool_result block to add
@@ -591,7 +593,10 @@ export class Task extends EventEmitter<TaskEvents> implements TaskLike {
 			)
 			return false
 		}
-		this.userMessageContent.push(toolResult)
+		// Keep results contiguous at the front: with parallel tool calls, an earlier tool's
+		// images or text are already queued, and Anthropic needs every tool_result first.
+		const lastResultIndex = findLastIndex(this.userMessageContent, (block) => block.type === "tool_result")
+		this.userMessageContent.splice(lastResultIndex + 1, 0, toolResult)
 		return true
 	}
 
@@ -5845,7 +5850,7 @@ export class Task extends EventEmitter<TaskEvents> implements TaskLike {
 		// For API only: merge consecutive user messages (excludes summary messages per
 		// mergeConsecutiveApiMessages implementation) without mutating stored history.
 		const mergedForApi = mergeConsecutiveApiMessages(messagesSinceLastSummary, { roles: ["user"] })
-		const messagesWithoutImages = maybeRemoveImageBlocks(mergedForApi, this.api)
+		const messagesWithoutImages = maybeRemoveImageBlocks(normalizeToolResultPairing(mergedForApi), this.api)
 		const cleanConversationHistory = this.buildCleanConversationHistory(
 			messagesWithoutImages as ApiMessage[],
 			requestModelInfo,

src/core/task/__tests__/Task.spec.ts

@@ -8171,6 +8171,30 @@ describe("pushToolResultToUserContent", () => {
 		warnSpy.mockRestore()
 	})
 
+	it("keeps tool_results ahead of images queued by earlier parallel tool calls", () => {
+		const task = new Task({
+			provider: mockProvider,
+			apiConfiguration: mockApiConfig,
+			task: "test task",
+			startTask: false,
+		})
+		const image: Anthropic.ImageBlockParam = {
+			type: "image",
+			source: { type: "base64", media_type: "image/png", data: "AAAA" },
+		}
+		const result = (id: string): Anthropic.ToolResultBlockParam => ({
+			type: "tool_result",
+			tool_use_id: id,
+			content: id,
+		})
+
+		task.pushToolResultToUserContent(result("A"))
+		task.userMessageContent.push(image)
+		task.pushToolResultToUserContent(result("B"))
+
+		expect(task.userMessageContent).toEqual([result("A"), result("B"), image])
+	})
+
 	it("should allow different tool_use_ids to be added", () => {
 		const task = new Task({
 			provider: mockProvider,
@@ -8247,8 +8271,9 @@ describe("pushToolResultToUserContent", () => {
 
 		expect(added).toBe(true)
 		expect(task.userMessageContent).toHaveLength(3)
-		expect(task.userMessageContent[0].type).toBe("text")
-		expect(task.userMessageContent[1].type).toBe("image")
-		expect(task.userMessageContent[2]).toEqual(toolResult)
+		// Tool results lead; other content keeps its relative order after them.
+		expect(task.userMessageContent[0]).toEqual(toolResult)
+		expect(task.userMessageContent[1].type).toBe("text")
+		expect(task.userMessageContent[2].type).toBe("image")
 	})
 })

src/core/task/__tests__/normalizeToolResultPairing.spec.ts

@@ -0,0 +1,81 @@
+import type { Anthropic } from "@anthropic-ai/sdk"
+
+import type { ApiMessage } from "../../task-persistence"
+import { normalizeToolResultPairing } from "../normalizeToolResultPairing"
+
+type Block = Anthropic.Messages.ContentBlockParam
+
+const use = (id: string): Block => ({ type: "tool_use", id, name: "read_file", input: {} })
+const result = (id: string, content = `result ${id}`): Block => ({ type: "tool_result", tool_use_id: id, content })
+const text = (value: string): Block => ({ type: "text", text: value })
+const image: Block = { type: "image", source: { type: "base64", media_type: "image/png", data: "AAAA" } }
+const assistant = (...content: Block[]): ApiMessage => ({ role: "assistant", content })
+const user = (...content: Block[]): ApiMessage => ({ role: "user", content })
+
+describe("normalizeToolResultPairing", () => {
+	it("moves interleaved tool results ahead of other content", () => {
+		const input = [
+			user(text("go")),
+			assistant(text("ok"), use("A"), use("B")),
+			user(result("A"), image, result("B")),
+		]
+
+		expect(normalizeToolResultPairing(input)[2].content).toEqual([result("A"), result("B"), image])
+	})
+
+	it("orders results by tool_use order and drops duplicates", () => {
+		const input = [assistant(use("A"), use("B")), user(result("B"), result("A"), result("A", "dup"))]
+
+		expect(normalizeToolResultPairing(input)[1].content).toEqual([result("A"), result("B")])
+	})
+
+	it("adds a synthetic error result for an interrupted tool_use", () => {
+		const input = [assistant(use("A"), use("B")), user(result("A"), text("next"))]
+
+		expect(normalizeToolResultPairing(input)[1].content).toEqual([
+			result("A"),
+			{ type: "tool_result", tool_use_id: "B", content: "Tool execution was interrupted before completion." },
+			text("next"),
+		])
+	})
+
+	it("inserts a user turn when an assistant turn is followed by another assistant turn", () => {
+		const out = normalizeToolResultPairing([assistant(use("A")), assistant(text("again"))])
+
+		expect(out.map((m) => m.role)).toEqual(["assistant", "user", "assistant"])
+		expect(out[1].content).toMatchObject([{ type: "tool_result", tool_use_id: "A" }])
+	})
+
+	it.each([
+		{ name: "result for an unknown id", messages: [assistant(use("A")), user(result("A"), result("X"))] },
+		{
+			name: "result after a text-only assistant turn",
+			messages: [assistant(text("hi")), user(result("X"), text("q"))],
+		},
+	])("drops orphan tool results: $name", ({ messages }) => {
+		const ids = normalizeToolResultPairing(messages)
+			.flatMap((m) => (Array.isArray(m.content) ? m.content : []))
+			.flatMap((b) => (b.type === "tool_result" ? [b.tool_use_id] : []))
+
+		expect(ids).not.toContain("X")
+	})
+
+	it("removes a user message that only held orphan results", () => {
+		expect(normalizeToolResultPairing([assistant(text("hi")), user(result("X"))])).toHaveLength(1)
+	})
+
+	it("leaves a trailing assistant tool_use and well-formed history unchanged", () => {
+		const wellFormed = [user(text("go")), assistant(use("A")), user(result("A"), text("done")), assistant(use("B"))]
+
+		expect(normalizeToolResultPairing(wellFormed)).toEqual(wellFormed)
+	})
+
+	it("does not mutate its input", () => {
+		const input = [assistant(use("A")), user(image, result("A"))]
+		const snapshot = structuredClone(input)
+
+		normalizeToolResultPairing(input)
+
+		expect(input).toEqual(snapshot)
+	})
+})

src/core/task/normalizeToolResultPairing.ts

@@ -0,0 +1,79 @@
+import { Anthropic } from "@anthropic-ai/sdk"
+
+import type { ApiMessage } from "../task-persistence"
+
+type Block = Anthropic.Messages.ContentBlockParam
+type ToolResultBlock = Anthropic.Messages.ToolResultBlockParam
+
+const INTERRUPTED_RESULT = "Tool execution was interrupted before completion."
+
+function toBlocks(content: ApiMessage["content"]): Block[] {
+	if (Array.isArray(content)) return content as Block[]
+	if (content === undefined || content === null || content === "") return []
+	return [{ type: "text", text: String(content) }]
+}
+
+function toolUseIdsOf(message: ApiMessage): string[] {
+	if (message.role !== "assistant" || !Array.isArray(message.content)) return []
+	return (message.content as Block[]).flatMap((block) => (block.type === "tool_use" ? [block.id] : []))
+}
+
+/**
+ * Shapes outgoing history so tool results satisfy Anthropic's adjacency rule: every
+ * `tool_use` in an assistant message is answered by a `tool_result` in the very next
+ * user message, `tool_result` blocks come first, and no `tool_result` refers to a
+ * `tool_use` outside the immediately preceding assistant message.
+ *
+ * - Results are moved ahead of other content, in `tool_use` order (duplicates dropped).
+ * - Results without a matching `tool_use` are dropped.
+ * - Interrupted calls get a synthetic error result.
+ *
+ * Used for API request shaping only; stored history is not mutated. A trailing assistant
+ * message is left alone because its results have not been produced yet.
+ */
+export function normalizeToolResultPairing(messages: ApiMessage[]): ApiMessage[] {
+	const out: ApiMessage[] = []
+
+	for (let i = 0; i < messages.length; i++) {
+		const message = messages[i]
+
+		if (message.role === "assistant") {
+			out.push(message)
+			const toolUseIds = toolUseIdsOf(message)
+			if (toolUseIds.length === 0 || i === messages.length - 1) continue
+
+			const next = messages[i + 1]
+			const nextBlocks = next.role === "user" ? toBlocks(next.content) : []
+			const resultsById = new Map<string, ToolResultBlock>()
+			for (const block of nextBlocks) {
+				if (block.type === "tool_result" && !resultsById.has(block.tool_use_id)) {
+					resultsById.set(block.tool_use_id, block)
+				}
+			}
+
+			const results: ToolResultBlock[] = toolUseIds.map(
+				(id) => resultsById.get(id) ?? { type: "tool_result", tool_use_id: id, content: INTERRUPTED_RESULT },
+			)
+
+			if (next.role === "user") {
+				const rest = nextBlocks.filter((block) => block.type !== "tool_result")
+				out.push({ ...next, content: [...results, ...rest] })
+				i++
+			} else {
+				// Another assistant message follows: answer the calls with a user turn of their own.
+				out.push({ role: "user", content: results })
+			}
+			continue
+		}
+
+		// A user message not directly after a tool_use turn cannot carry tool results.
+		if (!Array.isArray(message.content) || !message.content.some((block) => block.type === "tool_result")) {
+			out.push(message)
+			continue
+		}
+		const kept = (message.content as Block[]).filter((block) => block.type !== "tool_result")
+		if (kept.length > 0) out.push({ ...message, content: kept })
+	}
+
+	return out
+}