From ae8b8eeca32d3c3d0c5f1ecd779fadb69a81d97f Mon Sep 17 00:00:00 2001
From: Tom Boucher <trekkie@nomorestars.com>
Date: Tue, 17 Mar 2026 10:23:05 -0400
Subject: [PATCH] fix: limit native web_search to max_uses:5 per response
 (#817) (#869)

---
 src/resources/extensions/search-the-web/native-search.ts | 4 ++++
 src/tests/native-search.test.ts                          | 6 ++++--
 2 files changed, 8 insertions(+), 2 deletions(-)

diff --git a/src/resources/extensions/search-the-web/native-search.ts b/src/resources/extensions/search-the-web/native-search.ts
index f46bd42a4..3c50eda67 100644
--- a/src/resources/extensions/search-the-web/native-search.ts
+++ b/src/resources/extensions/search-the-web/native-search.ts
@@ -157,6 +157,10 @@ export function registerNativeSearchHooks(pi: NativeSearchPI): { getIsAnthropic:
     tools.push({
       type: "web_search_20250305",
       name: "web_search",
+      // Cap server-side searches per response to prevent the model from
+      // looping on web_search without synthesizing results (#817).
+      // 5 searches is generous — most queries need 1-2.
+      max_uses: 5,
     });
 
     return payload;
diff --git a/src/tests/native-search.test.ts b/src/tests/native-search.test.ts
index 09fd7597e..3547c0ce2 100644
--- a/src/tests/native-search.test.ts
+++ b/src/tests/native-search.test.ts
@@ -92,11 +92,12 @@ test("before_provider_request injects web_search for claude models", async () =>
   });
 
   const tools = (result as any)?.tools ?? payload.tools;
-  const hasNative = (tools as any[]).some(
+  const nativeTool = (tools as any[]).find(
     (t: any) => t.type === "web_search_20250305"
   );
-  assert.ok(hasNative, "Should inject web_search_20250305 tool");
+  assert.ok(nativeTool, "Should inject web_search_20250305 tool");
   assert.equal((tools as any[]).length, 2, "Should have original + injected tool");
+  assert.equal(nativeTool.max_uses, 5, "Should set max_uses to 5 to prevent search loops (#817)");
 });
 
 test("before_provider_request injects web_search for claude models even without model_select", async () => {
@@ -278,6 +279,7 @@ test("before_provider_request creates tools array if missing", async () => {
   assert.ok(Array.isArray(tools), "Should create tools array");
   assert.equal((tools as any[]).length, 1, "Should have exactly 1 tool");
   assert.equal((tools as any[])[0].type, "web_search_20250305");
+  assert.equal((tools as any[])[0].max_uses, 5, "Should include max_uses limit");
 });
 
 test("before_provider_request skips when payload is falsy", async () => {