diff --git a/packages/kbot/cpp/orchestrator/test-ipc-classifier.mjs b/packages/kbot/cpp/orchestrator/test-ipc-classifier.mjs
index f899cc72..d2a8b7c7 100644
--- a/packages/kbot/cpp/orchestrator/test-ipc-classifier.mjs
+++ b/packages/kbot/cpp/orchestrator/test-ipc-classifier.mjs
@@ -23,8 +23,9 @@
  * Stress (batch repeats, one worker): KBOT_CLASSIFIER_STRESS_RUNS=N (default 1)
  *   npm run test:ipc:classifier:openrouter:stress  → OpenRouter + 5 runs (override N via env)
  *
- * Reports (reports.js): cwd/tests/test-ipc-classifier__HH-mm.{json,md}; array-only distances in
+ * Reports (reports.js): cwd/tests/test-ipc-classifier__HH-mm.{json,md}; distances in
  * test-ipc-classifier-distances__HH-mm.json (same timestamp as the main JSON).
+ * With -F structured, the prompt asks for {"items":[...]} to match json_object APIs.
  */
 
 import { spawn } from 'node:child_process';
@@ -214,12 +215,15 @@ export const JOB_VIEWER_MACHINE_LABELS = [
 
 const ANCHOR = 'machine workshop';
 
-/** Build one prompt: model returns a JSON array only. */
+/** Keys we accept for the batch array when API forces a JSON object (e.g. response_format json_object). */
+const BATCH_ARRAY_OBJECT_KEYS = ['items', 'distances', 'results', 'data', 'labels', 'rows'];
+
+/** Build one prompt: plain mode = JSON array root; structured (-F structured) = JSON object with "items" (json_object API). */
 function classifierBatchPrompt(labels) {
   const numbered = labels.map((l, i) => `${i + 1}. ${JSON.stringify(l)}`).join('\n');
-  return `You classify business types against one anchor. Output ONLY a JSON array, no markdown fences, no commentary.
+  const structured = classifierFeatures.has('structured');
 
-Rules for each element:
+  const rules = `Rules for each element:
 - Use shape: {"label": <exact string from the list below>, "distance": <number>}
 - "distance" is semantic distance from 0 (same as anchor or direct synonym) to 10 (unrelated). One decimal allowed.
 - Include EXACTLY one object per line item below, in the SAME ORDER, with "label" copied character-for-character from the list.
@@ -227,29 +231,86 @@ Rules for each element:
 Anchor business type: ${ANCHOR}
 
 Candidate labels (in order):
-${numbered}
+${numbered}`;
+
+  if (structured) {
+    return `You classify business types against one anchor. Output ONLY valid JSON: one object, no markdown fences, no commentary.
+The API requires a JSON object (not a top-level array). Use exactly one top-level key "items" whose value is the array.
+
+${rules}
+
+Example: {"items":[{"label":"Example","distance":2.5},...]}`;
+  }
+
+  return `You classify business types against one anchor. Output ONLY a JSON array, no markdown fences, no commentary.
+
+${rules}
 
 Output: one JSON array, e.g. [{"label":"...","distance":2.5},...]`;
 }
 
+/**
+ * Parse model text into the batch array: root [...] or {"items":[...]} (json_object).
+ * @returns {unknown[] | null}
+ */
 function extractJsonArray(text) {
   if (!text || typeof text !== 'string') return null;
   let s = text.trim().replace(/^```(?:json)?\s*/i, '').replace(/\s*```$/u, '').trim();
+
+  /** @param {unknown} v */
+  const arrayFromParsed = (v) => {
+    if (Array.isArray(v)) return v;
+    if (!v || typeof v !== 'object') return null;
+    const o = /** @type {Record<string, unknown>} */ (v);
+    for (const key of BATCH_ARRAY_OBJECT_KEYS) {
+      const a = o[key];
+      if (Array.isArray(a)) return a;
+    }
+    for (const val of Object.values(o)) {
+      if (
+        Array.isArray(val) &&
+        val.length > 0 &&
+        val[0] &&
+        typeof val[0] === 'object' &&
+        val[0] !== null &&
+        'label' in val[0]
+      ) {
+        return val;
+      }
+    }
+    return null;
+  };
+
   try {
     const v = JSON.parse(s);
-    return Array.isArray(v) ? v : null;
+    return arrayFromParsed(v);
   } catch {
     /* fall through */
   }
+
   const i = s.indexOf('[');
   const j = s.lastIndexOf(']');
-  if (i < 0 || j <= i) return null;
-  try {
-    const v = JSON.parse(s.slice(i, j + 1));
-    return Array.isArray(v) ? v : null;
-  } catch {
-    return null;
+  if (i >= 0 && j > i) {
+    try {
+      const v = JSON.parse(s.slice(i, j + 1));
+      if (Array.isArray(v)) return v;
+    } catch {
+      /* ignore */
+    }
   }
+
+  const oi = s.indexOf('{');
+  const oj = s.lastIndexOf('}');
+  if (oi >= 0 && oj > oi) {
+    try {
+      const v = JSON.parse(s.slice(oi, oj + 1));
+      return arrayFromParsed(v);
+    } catch {
+      /* ignore */
+    }
+  }
+
+  return null;
 }
 
 /**
@@ -281,9 +342,9 @@ function normalizeBatchArray(arr, expectedLabels) {
 
 function batchTimeoutMs() {
   const raw = process.env.KBOT_CLASSIFIER_TIMEOUT_MS;
-  if (raw === undefined || raw === '') return 300_000;
+  if (raw === undefined || raw === '') return 30_000;
   const n = Number.parseInt(raw, 10);
-  return Number.isFinite(n) && n > 0 ? n : 300_000;
+  return Number.isFinite(n) && n > 0 ? n : 30_000;
 }
 
 /** Sequential batch iterations on one worker (stress). Default 1 = single run. */
@@ -326,7 +387,7 @@ function summarizeMs(values) {
 
 /** Log progress while awaiting a long LLM call (no silent hang). */
 function withHeartbeat(promise, ipcTimeoutMs, backendLabel) {
-  const every = 15_000;
+  const every = 10_000;
   let n = 0;
   const id = setInterval(() => {
     n += 1;
@@ -385,8 +446,8 @@ function processBatchResponse(p, labels) {
         parseError = `missing: ${missing.join('; ')}`;
       }
     } else {
-      assert(false, 'batch response parses as JSON array');
-      parseError = 'could not parse JSON array from model text';
+      assert(false, 'batch response parses as JSON array or {"items":[...]}');
+      parseError = 'could not parse batch array from model text';
     }
   } else {
     assert(false, 'kbot-ai success');
@@ -424,7 +485,9 @@ async function run() {
           `  ⚠️ -F structured: ignored for local llama (use --backend remote for response_format json_object)\n`
         );
       } else {
-        console.log(`  Structured: kbot-ai sends response_format {"type":"json_object"}\n`);
+        console.log(
+          `  Structured: response_format json_object + prompt asks for {"items":[...]} (not a top-level array)\n`
+        );
       }
     }
   }
diff --git a/packages/kbot/cpp/packages/kbot/llm_client.cpp b/packages/kbot/cpp/packages/kbot/llm_client.cpp
index b03f8c0d..ccfb4497 100644
--- a/packages/kbot/cpp/packages/kbot/llm_client.cpp
+++ b/packages/kbot/cpp/packages/kbot/llm_client.cpp
@@ -107,6 +107,7 @@ LLMResponse LLMClient::execute_chat(const std::string& prompt) {
             std::nullopt,
             std::nullopt,
             response_format);
+        logger::info("LLMClient: ChatCompletion returned (HTTP " + std::to_string(response.status_code) + ")");
         logger::debug("LLMClient::execute_chat: Got response with status: " + std::to_string(response.status_code));
 
         // liboai may not populate raw_json for custom base URLs — parse content directly.
diff --git a/packages/kbot/cpp/packages/liboai/liboai/core/netimpl.cpp b/packages/kbot/cpp/packages/liboai/liboai/core/netimpl.cpp
index 6a274f00..a45d4a3c 100644
--- a/packages/kbot/cpp/packages/liboai/liboai/core/netimpl.cpp
+++ b/packages/kbot/cpp/packages/liboai/liboai/core/netimpl.cpp
@@ -1325,16 +1325,35 @@ void liboai::netimpl::Session::SetOption(const components::Timeout& timeout) {
 }
 
 void liboai::netimpl::Session::SetTimeout(const components::Timeout& timeout) {
-	CURLcode e = curl_easy_setopt(this->curl_, CURLOPT_TIMEOUT_MS, timeout.Milliseconds());
+	const long ms = timeout.Milliseconds();
+	CURLcode e = curl_easy_setopt(this->curl_, CURLOPT_TIMEOUT_MS, ms);
+	ErrorCheck(e, "liboai::netimpl::Session::SetTimeout()");
+
+	/* Connection phase (DNS/TCP/TLS) is governed separately; without this, some stacks
+	   can sit in connect/handshake longer than expected while the transfer timer is idle. */
+	if (ms > 0) {
+		/* Avoid std::min — Windows headers may define min() as a macro. */
+		const long connect_ms = (ms < 120000L) ? ms : 120000L;
+		e = curl_easy_setopt(this->curl_, CURLOPT_CONNECTTIMEOUT_MS, connect_ms);
+		ErrorCheck(e, "liboai::netimpl::Session::SetTimeout() (connect)");
+
+		#if defined(LIBOAI_DEBUG)
+			_liboai_dbg(
+				"[dbg] [@%s] Set connect timeout to %ld milliseconds\n",
+				__func__, connect_ms
+			);
+		#endif
+	}
+
+	e = curl_easy_setopt(this->curl_, CURLOPT_NOSIGNAL, 1L);
+	ErrorCheck(e, "liboai::netimpl::Session::SetTimeout() (nosignal)");
 
 	#if defined(LIBOAI_DEBUG)
 		_liboai_dbg(
 			"[dbg] [@%s] Set timeout to %ld milliseconds\n",
-			__func__, timeout.Milliseconds()
+			__func__, ms
 		);
 	#endif
-		
-	ErrorCheck(e, "liboai::netimpl::Session::SetTimeout()");
 }
 
 void liboai::netimpl::Session::SetOption(const components::Proxies& proxies) {