diff --git a/scripts/e2e/parallels-macos-smoke.sh b/scripts/e2e/parallels-macos-smoke.sh
index c7c6e7179f7..ff27557b452 100644
--- a/scripts/e2e/parallels-macos-smoke.sh
+++ b/scripts/e2e/parallels-macos-smoke.sh
@@ -1460,15 +1460,33 @@ EOF
 }
 
 verify_gateway() {
-  local attempt deadline
+  local attempt deadline probe_json
   attempt=1
   deadline=$((SECONDS + TIMEOUT_GATEWAY_S))
   while (( SECONDS < deadline )); do
-    if guest_current_user_exec "$GUEST_OPENCLAW_BIN" gateway status --deep --require-rpc --timeout 30000; then
+    if probe_json="$(
+      guest_current_user_exec "$GUEST_OPENCLAW_BIN" gateway probe \
+        --url ws://127.0.0.1:18789 \
+        --timeout 30000 \
+        --json
+    )"; then
+      printf '%s\n' "$probe_json"
+      if PROBE_JSON="$probe_json" python3 - <<'PY'
+import json
+import os
+
+payload = json.loads(os.environ["PROBE_JSON"])
+raise SystemExit(0 if payload.get("ok") else 1)
+PY
+      then
+        return 0
+      fi
+    elif ! guest_current_user_exec "$GUEST_OPENCLAW_BIN" gateway probe --help >/dev/null 2>&1 &&
+      guest_current_user_exec "$GUEST_OPENCLAW_BIN" gateway status --deep --require-rpc --timeout 30000; then
       return 0
     fi
     if (( SECONDS < deadline )); then
-      printf 'gateway-status retry %s\n' "$attempt" >&2
+      printf 'gateway-probe retry %s\n' "$attempt" >&2
       sleep 5
     fi
     attempt=$((attempt + 1))
diff --git a/scripts/e2e/parallels-windows-smoke.sh b/scripts/e2e/parallels-windows-smoke.sh
index e57ec4b6ec3..02cffbebea9 100644
--- a/scripts/e2e/parallels-windows-smoke.sh
+++ b/scripts/e2e/parallels-windows-smoke.sh
@@ -52,7 +52,7 @@ TIMEOUT_ONBOARD_S=600
 TIMEOUT_ONBOARD_PHASE_S=$((TIMEOUT_ONBOARD_S + 120))
 # verify_gateway_reachable runs six 30s probes plus short retry sleeps.
 TIMEOUT_GATEWAY_S=420
-TIMEOUT_AGENT_S="${OPENCLAW_PARALLELS_WINDOWS_AGENT_TIMEOUT_S:-900}"
+TIMEOUT_AGENT_S="${OPENCLAW_PARALLELS_WINDOWS_AGENT_TIMEOUT_S:-1500}"
 PHASE_STALE_WARN_S=60
 
 FRESH_MAIN_STATUS="skip"
diff --git a/test/scripts/parallels-smoke-model.test.ts b/test/scripts/parallels-smoke-model.test.ts
index 46b6d6bd0f4..6c3f7da22e4 100644
--- a/test/scripts/parallels-smoke-model.test.ts
+++ b/test/scripts/parallels-smoke-model.test.ts
@@ -52,6 +52,8 @@ describe("Parallels smoke model selection", () => {
     const script = readFileSync("scripts/e2e/parallels-macos-smoke.sh", "utf8");
 
     expect(script).toContain("deadline=$((SECONDS + TIMEOUT_GATEWAY_S))");
+    expect(script).toContain("gateway probe");
+    expect(script).toContain("--url ws://127.0.0.1:18789");
     expect(script).toContain("gateway status --deep --require-rpc --timeout 30000");
   });
 
@@ -61,4 +63,12 @@ describe("Parallels smoke model selection", () => {
     expect(script).toContain('agent_log="/tmp/openclaw-parallels-agent-turn.log"');
     expect(script).toContain("run_logged_guest_current_user_sh");
   });
+
+  it("keeps the Windows first agent turn patient enough for cold package startup", () => {
+    const script = readFileSync("scripts/e2e/parallels-windows-smoke.sh", "utf8");
+
+    expect(script).toContain(
+      'TIMEOUT_AGENT_S="${OPENCLAW_PARALLELS_WINDOWS_AGENT_TIMEOUT_S:-1500}"',
+    );
+  });
 });