From 1211727ba351c9de104d27296f844fe9c90193d2 Mon Sep 17 00:00:00 2001
From: "google-labs-jules[bot]"
 <161369871+google-labs-jules[bot]@users.noreply.github.com>
Date: Fri, 28 Nov 2025 18:53:12 +0000
Subject: [PATCH] feat(anthropic): add validation for arbitrary json objects in
 structured outputs

Anthropic models do not support arbitrary JSON objects (e.g. f.json() or f.object() with no properties) in structured outputs. This commit adds a validation step that throws a descriptive error when this unsupported schema is detected, preventing the API from returning a cryptic "Bad Request" error.

For valid structured objects, this commit also ensures `additionalProperties: false` is set recursively, which is required by the Anthropic API.

A new test case has been added to verify the error-throwing behavior.
---
 src/ax/ai/anthropic/api.test.ts | 47 +++++++++++++++++++++++++++++++++
 src/ax/ai/anthropic/api.ts      | 46 ++++++++++++++------------------
 2 files changed, 67 insertions(+), 26 deletions(-)

diff --git a/src/ax/ai/anthropic/api.test.ts b/src/ax/ai/anthropic/api.test.ts
index 8df65113..ef22b81a 100644
--- a/src/ax/ai/anthropic/api.test.ts
+++ b/src/ax/ai/anthropic/api.test.ts
@@ -56,6 +56,53 @@ describe('AxAIAnthropic model key preset merging', () => {
   });
 });
 
+describe('AxAIAnthropic schema validation', () => {
+  it('should throw an error for arbitrary JSON objects in structured outputs', async () => {
+    const ai = new AxAIAnthropic({
+      apiKey: 'key',
+      config: { model: AxAIAnthropicModel.Claude35Sonnet },
+    });
+
+    const fetch = createMockFetch({
+      id: 'id',
+      type: 'message',
+      role: 'assistant',
+      content: [{ type: 'text', text: 'ok' }],
+      model: 'claude-3-5-sonnet-latest',
+      stop_reason: 'end_turn',
+      usage: { input_tokens: 1, output_tokens: 1 },
+    });
+
+    ai.setOptions({ fetch });
+
+    await expect(
+      ai.chat({
+        chatPrompt: [{ role: 'user', content: 'hi' }],
+        responseFormat: {
+          type: 'json_schema',
+          schema: {
+            type: 'object',
+            properties: {
+              arbitrary: {
+                type: [
+                  'object',
+                  'array',
+                  'string',
+                  'number',
+                  'boolean',
+                  'null',
+                ],
+              },
+            },
+          },
+        },
+      })
+    ).rejects.toThrow(
+      'Anthropic models do not support arbitrary JSON objects (e.g. f.json() or f.object() with no properties) in structured outputs. Please use f.string() and instruct the model to return a JSON string, or define the expected structure with f.object({ ... })'
+    );
+  });
+});
+
 describe('AxAIAnthropic trims trailing whitespace in assistant content', () => {
   it('removes trailing whitespace from assistant string content in request body', async () => {
     const ai = new AxAIAnthropic({
diff --git a/src/ax/ai/anthropic/api.ts b/src/ax/ai/anthropic/api.ts
index daebe90d..7bfecdab 100644
--- a/src/ax/ai/anthropic/api.ts
+++ b/src/ax/ai/anthropic/api.ts
@@ -30,23 +30,26 @@ import {
   AxAIAnthropicVertexModel,
 } from './types.js';
 
-/**
- * Clean function schema for Anthropic API compatibility
- * Anthropic uses input_schema and may not support certain JSON Schema fields
- */
-const cleanSchemaForAnthropic = (
-  schema: any,
-  preserveAdditionalProperties: boolean = false
-): any => {
+const cleanSchemaForAnthropic = (schema: any): any => {
   if (!schema || typeof schema !== 'object') {
     return schema;
   }
 
   const cleaned = { ...schema };
 
-  // Remove fields that might cause issues with Anthropic
-  if (!preserveAdditionalProperties) {
-    delete cleaned.additionalProperties;
+  const isObjectType =
+    cleaned.type === 'object' ||
+    (Array.isArray(cleaned.type) && cleaned.type.includes('object'));
+
+  if (isObjectType) {
+    if (!cleaned.properties || Object.keys(cleaned.properties).length === 0) {
+      throw new Error(
+        'Anthropic models do not support arbitrary JSON objects (e.g. f.json() or f.object() with no properties) in structured outputs. Please use f.string() and instruct the model to return a JSON string, or define the expected structure with f.object({ ... })'
+      );
+    }
+    if (cleaned.additionalProperties === undefined) {
+      cleaned.additionalProperties = false;
+    }
   }
 
   // Anthropic supports default, anyOf, allOf, const, enum.
@@ -62,34 +65,25 @@ const cleanSchemaForAnthropic = (
     cleaned.properties = Object.fromEntries(
       Object.entries(cleaned.properties).map(([key, value]) => [
         key,
-        cleanSchemaForAnthropic(value, preserveAdditionalProperties),
+        cleanSchemaForAnthropic(value),
       ])
     );
   }
 
   // Recursively clean items (for arrays)
   if (cleaned.items) {
-    cleaned.items = cleanSchemaForAnthropic(
-      cleaned.items,
-      preserveAdditionalProperties
-    );
+    cleaned.items = cleanSchemaForAnthropic(cleaned.items);
   }
 
   // Recursively clean anyOf, allOf, oneOf
   if (Array.isArray(cleaned.anyOf)) {
-    cleaned.anyOf = cleaned.anyOf.map((s: any) =>
-      cleanSchemaForAnthropic(s, preserveAdditionalProperties)
-    );
+    cleaned.anyOf = cleaned.anyOf.map((s: any) => cleanSchemaForAnthropic(s));
   }
   if (Array.isArray(cleaned.allOf)) {
-    cleaned.allOf = cleaned.allOf.map((s: any) =>
-      cleanSchemaForAnthropic(s, preserveAdditionalProperties)
-    );
+    cleaned.allOf = cleaned.allOf.map((s: any) => cleanSchemaForAnthropic(s));
   }
   if (Array.isArray(cleaned.oneOf)) {
-    cleaned.oneOf = cleaned.oneOf.map((s: any) =>
-      cleanSchemaForAnthropic(s, preserveAdditionalProperties)
-    );
+    cleaned.oneOf = cleaned.oneOf.map((s: any) => cleanSchemaForAnthropic(s));
   }
 
   return cleaned;
@@ -423,7 +417,7 @@ class AxAIAnthropicImpl
 
         outputFormat = {
           type: 'json_schema',
-          schema: cleanSchemaForAnthropic(schema, true),
+          schema: cleanSchemaForAnthropic(schema),
         };
         this.usedStructuredOutput = true;
       }