From 3bc6eebacf3a6497eb82a66e02ca8644cfa3dde2 Mon Sep 17 00:00:00 2001
From: David Brailovsky <davidbrai@gmail.com>
Date: Thu, 22 Oct 2026 12:43:26 +0200
Subject: [PATCH] fix(ai): hold Anthropic system updates past dropped assistant
 messages

A mid-conversation system message was placed before checking whether the
next assistant message converts to any blocks. When it did not (empty text,
or another model's reasoning-only reply), the update landed before a user
message and Claude rejected the request with a 400.

closes #11091
---
 packages/ai/CHANGELOG.md                      |  4 ++
 packages/ai/src/api/anthropic-messages.ts     |  6 ++-
 .../ai/test/transcript-tool-changes.test.ts   | 46 ++++++++++++++++++-
 3 files changed, 53 insertions(+), 3 deletions(-)

diff --git a/packages/ai/CHANGELOG.md b/packages/ai/CHANGELOG.md
index 0c9fcee1d..74aa15c4d 100644
--- a/packages/ai/CHANGELOG.md
+++ b/packages/ai/CHANGELOG.md
@@ -2,6 +2,10 @@
 
 ## [Unreleased]
 
+### Fixed
+
+- Fixed Claude models that accept mid-conversation system messages rejecting a session with a 400 (`role 'system' must precede an 'assistant' message`) when a system update was followed by an assistant reply with nothing to send to Anthropic, such as an empty reply or another model's reasoning-only reply ([#11091](https://github.com/earendil-works/pi/issues/11091))
+
 ## [1.4.0] - 2026-10-21
 
 ### Breaking Changes
diff --git a/packages/ai/src/api/anthropic-messages.ts b/packages/ai/src/api/anthropic-messages.ts
index 761ccd1e9..b43b11c0e 100644
--- a/packages/ai/src/api/anthropic-messages.ts
+++ b/packages/ai/src/api/anthropic-messages.ts
@@ -1375,7 +1375,9 @@ function convertMessages(
 	const params: MessageParam[] = [];
 	const assistantLevels = new Map<number, AnthropicEffort>();
 	// Later system messages are held back and emitted directly before the next assistant
-	// message (or at the end of the transcript). Anthropic requires `tool_result` blocks to
+	// message that is sent (or at the end of the transcript). Assistant messages that convert to
+	// no blocks are dropped, so holding past them keeps an update from landing before a user
+	// message (#11091). Anthropic requires `tool_result` blocks to
 	// immediately follow their `tool_use`, so a system message between them is rejected; this
 	// also mirrors where the managed-effort system messages are inserted. As a result an
 	// update placed before a user message in the transcript lands after it on the wire.
@@ -1442,7 +1444,6 @@ function convertMessages(
 				});
 			}
 		} else if (msg.role === "assistant") {
-			flushPendingSystemMessages();
 			const blocks: ContentBlockParam[] = [];
 
 			for (const block of msg.content) {
@@ -1497,6 +1498,7 @@ function convertMessages(
 				}
 			}
 			if (blocks.length === 0) continue;
+			flushPendingSystemMessages();
 			const messageIndex = params.length;
 			params.push({
 				role: "assistant",
diff --git a/packages/ai/test/transcript-tool-changes.test.ts b/packages/ai/test/transcript-tool-changes.test.ts
index 03127cd24..caaa7fe12 100644
--- a/packages/ai/test/transcript-tool-changes.test.ts
+++ b/packages/ai/test/transcript-tool-changes.test.ts
@@ -1,7 +1,7 @@
 import { Type } from "typebox";
 import { describe, expect, test } from "vitest";
 import { getModel, streamSimple } from "../src/compat.ts";
-import type { Api, Context, Message, Model, SystemMessage, Tool } from "../src/types.ts";
+import type { Api, AssistantMessage, Context, Message, Model, SystemMessage, Tool } from "../src/types.ts";
 import { resolveTranscriptTools } from "../src/utils/transcript.ts";
 
 class PayloadCaptured extends Error {}
@@ -244,6 +244,50 @@ describe("transcript system messages", () => {
 		expect(payload.messages.at(-1)?.content.map((block) => block.type)).toEqual(["text"]);
 	});
 
+	// #11091
+	test("holds an Anthropic update past an assistant message that converts to no blocks", async () => {
+		const reply = (text: string, provider: string, api: Api, model: string): AssistantMessage => ({
+			role: "assistant",
+			content: [{ type: "text", text }],
+			api,
+			provider,
+			model,
+			usage: {
+				input: 0,
+				output: 0,
+				cacheRead: 0,
+				cacheWrite: 0,
+				totalTokens: 0,
+				cost: { input: 0, output: 0, cacheRead: 0, cacheWrite: 0, total: 0 },
+			},
+			stopReason: "stop",
+			timestamp: 3,
+		});
+		const messages: Message[] = [
+			{ role: "system", content: "base prompt", timestamp: 0 },
+			{ role: "user", content: "hi", timestamp: 1 },
+			{ role: "system", content: "updated guidance", timestamp: 2 },
+			// Another model's empty reply: Anthropic rejects empty text blocks, so it is dropped.
+			reply("", "openai-codex", "openai-codex-responses", "gpt-x"),
+			{ role: "user", content: "again", timestamp: 4 },
+		];
+		const roles = (payload: AnthropicPayload) => payload.messages.map((message) => message.role);
+
+		// No later assistant: the update goes at the end.
+		const atEnd = await capturePayload<AnthropicPayload>(anthropicNativeModel, { messages });
+		expect(roles(atEnd)).toEqual(["user", "user", "system"]);
+
+		// A later assistant that is sent: the update goes directly before it.
+		const beforeAssistant = await capturePayload<AnthropicPayload>(anthropicNativeModel, {
+			messages: [
+				...messages,
+				reply("answer", anthropicNativeModel.provider, anthropicNativeModel.api, anthropicNativeModel.id),
+				{ role: "user", content: "third", timestamp: 5 },
+			],
+		});
+		expect(roles(beforeAssistant)).toEqual(["user", "user", "system", "assistant", "user"]);
+	});
+
 	test("folds Anthropic updates into the system prompt without native support", async () => {
 		const model: Model<"anthropic-messages"> = {
 			...modelBase,