From 4da0afa5ca87c21950866f49964cf00ee5b3063e Mon Sep 17 00:00:00 2001
From: Major Hayden <major@mhtx.net>
Date: Wed, 19 Aug 2026 14:12:36 -0500
Subject: [PATCH] fix(ai): preserve Vertex Anthropic tool continuations

- fold terminal system updates into Vertex local tool-result turns

- preserve native system updates for direct Anthropic and ordinary Vertex requests

Refs #43478

Signed-off-by: Major Hayden <major@mhtx.net>
---
 .../ai/src/protocols/anthropic-messages.ts    |  11 +-
 .../test/provider/anthropic-messages.test.ts  | 107 ++++++++++++++++++
 2 files changed, 117 insertions(+), 1 deletion(-)

diff --git a/packages/ai/src/protocols/anthropic-messages.ts b/packages/ai/src/protocols/anthropic-messages.ts
index 3c31699694bd..65ce4be0ed6b 100644
--- a/packages/ai/src/protocols/anthropic-messages.ts
+++ b/packages/ai/src/protocols/anthropic-messages.ts
@@ -502,7 +502,16 @@ const lowerMessages = Effect.fn("AnthropicMessages.lowerMessages")(function* (
     if (message.role === "system") {
       if (splitsLocalToolResults(request.messages, index))
         return yield* invalid("Anthropic Messages system updates cannot split a local tool call from its tool result")
-      if (supportsNativeSystemUpdates(request) && canUseNativeSystemUpdate(request.messages, index)) {
+      // Vertex currently returns 404 for a terminal system message after local tool results.
+      const vertexToolResultUpdate =
+        request.model.provider === "google-vertex" &&
+        request.messages[index - 1]?.role === "tool" &&
+        request.messages[index + 1] === undefined
+      if (
+        supportsNativeSystemUpdates(request) &&
+        !vertexToolResultUpdate &&
+        canUseNativeSystemUpdate(request.messages, index)
+      ) {
         messages.push(yield* lowerNativeSystemUpdate(message, breakpoints))
         continue
       }
diff --git a/packages/ai/test/provider/anthropic-messages.test.ts b/packages/ai/test/provider/anthropic-messages.test.ts
index 8eb9ef31394b..b178a558d532 100644
--- a/packages/ai/test/provider/anthropic-messages.test.ts
+++ b/packages/ai/test/provider/anthropic-messages.test.ts
@@ -18,6 +18,14 @@ const opus48 = AnthropicMessages.route
   .with({ endpoint: { baseURL: "https://api.anthropic.test/v1/" }, auth: Auth.header("x-api-key", "test") })
   .model({ id: "claude-opus-4-8" })
 
+const vertexOpus48 = AnthropicMessages.route
+  .with({
+    provider: "google-vertex",
+    endpoint: { baseURL: "https://vertex.test/v1/" },
+    auth: Auth.header("authorization", "Bearer test"),
+  })
+  .model({ id: "claude-opus-4-8" })
+
 const request = LLM.request({
   id: "req_1",
   model,
@@ -277,6 +285,105 @@ describe("Anthropic Messages route", () => {
     }),
   )
 
+  it.effect("keeps a terminal Vertex system update in the tool-result turn", () =>
+    Effect.gen(function* () {
+      const prepared = yield* compileRequest(
+        LLM.request({
+          model: vertexOpus48,
+          messages: [
+            Message.assistant([ToolCallPart.make({ id: "call_1", name: "lookup", input: {} })]),
+            Message.tool({ id: "call_1", name: "lookup", result: "Done." }),
+            Message.system("Operator update."),
+          ],
+          cache: "none",
+        }),
+      )
+
+      expect(prepared.body.messages).toEqual([
+        {
+          role: "assistant",
+          content: [{ type: "tool_use", id: "call_1", name: "lookup", input: {} }],
+        },
+        {
+          role: "user",
+          content: [
+            {
+              type: "tool_result",
+              tool_use_id: "call_1",
+              content: '"Done."',
+              is_error: undefined,
+              cache_control: undefined,
+            },
+            {
+              type: "text",
+              text: "<system-update>\nOperator update.\n</system-update>",
+              cache_control: undefined,
+            },
+          ],
+        },
+      ])
+    }),
+  )
+
+  it.effect("keeps a terminal direct Anthropic system update native", () =>
+    Effect.gen(function* () {
+      const prepared = yield* compileRequest(
+        LLM.request({
+          model: opus48,
+          messages: [
+            Message.assistant([ToolCallPart.make({ id: "call_1", name: "lookup", input: {} })]),
+            Message.tool({ id: "call_1", name: "lookup", result: "Done." }),
+            Message.system("Operator update."),
+          ],
+          cache: "none",
+        }),
+      )
+
+      expect(prepared.body.messages).toEqual([
+        {
+          role: "assistant",
+          content: [{ type: "tool_use", id: "call_1", name: "lookup", input: {} }],
+        },
+        {
+          role: "user",
+          content: [
+            {
+              type: "tool_result",
+              tool_use_id: "call_1",
+              content: '"Done."',
+              is_error: undefined,
+              cache_control: undefined,
+            },
+          ],
+        },
+        {
+          role: "system",
+          content: [{ type: "text", text: "Operator update.", cache_control: undefined }],
+        },
+      ])
+    }),
+  )
+
+  it.effect("keeps an ordinary terminal Vertex system update native", () =>
+    Effect.gen(function* () {
+      const prepared = yield* compileRequest(
+        LLM.request({
+          model: vertexOpus48,
+          messages: [Message.user("Before."), Message.system("Operator update.")],
+          cache: "none",
+        }),
+      )
+
+      expect(prepared.body.messages).toEqual([
+        { role: "user", content: [{ type: "text", text: "Before." }] },
+        {
+          role: "system",
+          content: [{ type: "text", text: "Operator update.", cache_control: undefined }],
+        },
+      ])
+    }),
+  )
+
   it.effect("rejects a system update between a local tool call and its result", () =>
     Effect.gen(function* () {
       const error = yield* compileRequest(