diff --git a/docs/advanced/configuration.mdx b/docs/advanced/configuration.mdx
index a444b497..61128d6b 100644
--- a/docs/advanced/configuration.mdx
+++ b/docs/advanced/configuration.mdx
@@ -37,6 +37,11 @@ Configure Strix using environment variables or a config file.
   Request timeout in seconds for LLM calls.
 </ParamField>
 
+<ParamField path="LLM_PREFLIGHT_TIMEOUT" default="30" type="integer">
+  Seconds the startup connection check waits for the model to answer before
+  failing with `LLM CONNECTION FAILED`. Scan requests use `LLM_TIMEOUT`.
+</ParamField>
+
 <ParamField path="STRIX_LLM_MAX_RETRIES" default="5" type="integer">
   Maximum number of retries for LLM API calls on transient failures.
 </ParamField>
diff --git a/strix/config/settings.py b/strix/config/settings.py
index d0474612..54243b74 100644
--- a/strix/config/settings.py
+++ b/strix/config/settings.py
@@ -77,6 +77,7 @@ class LlmSettings(BaseSettings):
         alias="LLM_DISABLE_STREAMING",
     )
     timeout: int = Field(default=300, alias="LLM_TIMEOUT")
+    preflight_timeout: int = Field(default=30, ge=1, alias="LLM_PREFLIGHT_TIMEOUT")
     stream_idle_timeout: int = Field(default=300, ge=0, alias="LLM_STREAM_IDLE_TIMEOUT")
     max_tool_calls_per_turn: int = Field(
         default=32,
diff --git a/strix/interface/main.py b/strix/interface/main.py
index 1ebccffb..18f9113d 100644
--- a/strix/interface/main.py
+++ b/strix/interface/main.py
@@ -36,6 +36,7 @@ from strix.interface.interactive import (
 from strix.interface.scan_setup import (
     ModelConnectionError,
     preflight_model_connection,
+    preflight_request,
     prepare_run,
     telemetry_start,
 )
@@ -106,13 +107,10 @@ def _subscription_error_hint(exc: BaseException) -> str | None:
 
 
 async def warm_up_llm() -> None:
-    from agents.models.interface import ModelTracing
-
     from strix.config.models import (
         configure_sdk_model_defaults,
         is_known_openai_bare_model,
     )
-    from strix.core.inputs import make_model_settings
 
     console = Console()
     logger.info("Warming up LLM connection")
@@ -166,28 +164,11 @@ async def warm_up_llm() -> None:
             # A dedicated dedupe model may route to another provider, which must
             # never receive the main endpoint's headers; it has its own
             # DEDUPE_LLM_EXTRA_HEADERS.
-            deduper_settings = make_model_settings(
-                None,
+            await preflight_request(
+                deduper,
                 model_name=dedupe_model,
-                request_timeout=llm.timeout,
-                prompt_cache=False,
                 extra_headers=settings.dedupe.extra_headers,
-                has_tools=False,
-            )
-            await asyncio.wait_for(
-                deduper.get_response(
-                    system_instructions="You are a helpful assistant.",
-                    input="Reply with just 'OK'.",
-                    model_settings=deduper_settings,
-                    tools=[],
-                    output_schema=None,
-                    handoffs=[],
-                    tracing=ModelTracing.DISABLED,
-                    previous_response_id=None,
-                    conversation_id=None,
-                    prompt=None,
-                ),
-                timeout=llm.timeout,
+                timeout=llm.preflight_timeout,
             )
             logger.info("LLM warm-up succeeded for dedupe model %s", dedupe_model)
 
diff --git a/strix/interface/scan_setup.py b/strix/interface/scan_setup.py
index 2b070bd0..d7d0aab6 100644
--- a/strix/interface/scan_setup.py
+++ b/strix/interface/scan_setup.py
@@ -46,6 +46,8 @@ from strix.utils.api_spec import (
 if TYPE_CHECKING:
     import argparse
 
+    from agents.models.interface import Model
+
 logger = logging.getLogger(__name__)
 
 HOST_GATEWAY_HOSTNAME = "host.docker.internal"
@@ -104,38 +106,61 @@ async def preflight_model_connection(
     settings: Settings | None = None,
 ) -> None:
     """Verify the configured model route before starting a scan."""
-    from agents.models.interface import ModelTracing
-
     from strix.config.models import StrixProvider, configure_sdk_model_defaults
-    from strix.core.inputs import make_model_settings
 
     resolved_settings = load_settings() if settings is None else settings
     check_header_safe_credentials(resolved_settings)
     configure_sdk_model_defaults(resolved_settings)
     model = StrixProvider().get_model(model_name)
+    await preflight_request(
+        model,
+        model_name=model_name,
+        extra_headers=resolved_settings.llm.extra_headers,
+        timeout=resolved_settings.llm.preflight_timeout,
+    )
+
+
+async def preflight_request(
+    model: Model,
+    *,
+    model_name: str,
+    extra_headers: dict[str, str] | None,
+    timeout: int,
+) -> None:
+    """Send one tiny request to ``model`` and fail if it does not answer in ``timeout`` seconds."""
+    from agents.models.interface import ModelTracing
+
+    from strix.core.inputs import make_model_settings
+
     request_settings = make_model_settings(
         None,
         model_name=model_name,
-        request_timeout=resolved_settings.llm.timeout,
+        request_timeout=timeout,
         prompt_cache=False,
-        extra_headers=resolved_settings.llm.extra_headers,
+        extra_headers=extra_headers,
         has_tools=False,
     )
-    await asyncio.wait_for(
-        model.get_response(
-            system_instructions="You are a helpful assistant.",
-            input="Reply with just 'OK'.",
-            model_settings=request_settings,
-            tools=[],
-            output_schema=None,
-            handoffs=[],
-            tracing=ModelTracing.DISABLED,
-            previous_response_id=None,
-            conversation_id=None,
-            prompt=None,
-        ),
-        timeout=resolved_settings.llm.timeout,
-    )
+    try:
+        await asyncio.wait_for(
+            model.get_response(
+                system_instructions="You are a helpful assistant.",
+                input="Reply with just 'OK'.",
+                model_settings=request_settings,
+                tools=[],
+                output_schema=None,
+                handoffs=[],
+                tracing=ModelTracing.DISABLED,
+                previous_response_id=None,
+                conversation_id=None,
+                prompt=None,
+            ),
+            timeout=timeout,
+        )
+    except TimeoutError:
+        raise TimeoutError(
+            f"{model_name} did not answer within {timeout}s "
+            "(LLM_PREFLIGHT_TIMEOUT). Check LLM_API_BASE and that the endpoint is reachable."
+        ) from None
 
 
 def build_targets_info(args: argparse.Namespace) -> None:
diff --git a/tests/test_preflight_timeout.py b/tests/test_preflight_timeout.py
new file mode 100644
index 00000000..28f40b3f
--- /dev/null
+++ b/tests/test_preflight_timeout.py
@@ -0,0 +1,84 @@
+"""The startup model check has its own short timeout; scan requests keep LLM_TIMEOUT."""
+
+from __future__ import annotations
+
+import asyncio
+import time
+from typing import TYPE_CHECKING, Any
+
+import pytest
+
+from strix.config import load_settings, loader
+from strix.interface import scan_setup
+from strix.interface.scan_setup import preflight_model_connection, preflight_request
+
+
+if TYPE_CHECKING:
+    from pathlib import Path
+
+
+def _fresh_settings(monkeypatch: pytest.MonkeyPatch, tmp_path: Path) -> None:
+    monkeypatch.setattr(loader, "_cached", None)
+    monkeypatch.setattr(loader, "_override", tmp_path / "no-cli-config.json")
+
+
+class _NeverAnswers:
+    def __init__(self) -> None:
+        self.request_timeouts: list[float | None] = []
+
+    async def get_response(self, *, model_settings: Any, **_: Any) -> None:
+        self.request_timeouts.append((model_settings.extra_args or {}).get("timeout"))
+        await asyncio.sleep(3600)
+
+
+def test_preflight_timeout_defaults_to_30s_and_is_separate_from_llm_timeout(
+    monkeypatch: pytest.MonkeyPatch, tmp_path: Path
+) -> None:
+    monkeypatch.delenv("LLM_PREFLIGHT_TIMEOUT", raising=False)
+    monkeypatch.setenv("LLM_TIMEOUT", "600")
+    _fresh_settings(monkeypatch, tmp_path)
+    llm = load_settings().llm
+    assert llm.timeout == 600
+    assert llm.preflight_timeout == 30
+
+    monkeypatch.setenv("LLM_PREFLIGHT_TIMEOUT", "7")
+    _fresh_settings(monkeypatch, tmp_path)
+    assert load_settings().llm.preflight_timeout == 7
+
+
+def test_preflight_request_fails_after_its_own_timeout_with_a_clear_message() -> None:
+    model = _NeverAnswers()
+    started = time.monotonic()
+    with pytest.raises(TimeoutError) as excinfo:
+        asyncio.run(
+            preflight_request(
+                model,  # type: ignore[arg-type]
+                model_name="openai/gpt-4o",
+                extra_headers=None,
+                timeout=1,
+            )
+        )
+    assert time.monotonic() - started < 5
+    message = str(excinfo.value)
+    assert "openai/gpt-4o did not answer within 1s" in message
+    assert "LLM_PREFLIGHT_TIMEOUT" in message
+    assert model.request_timeouts == [1]
+
+
+def test_preflight_model_connection_uses_the_preflight_timeout(
+    monkeypatch: pytest.MonkeyPatch, tmp_path: Path
+) -> None:
+    monkeypatch.setenv("STRIX_LLM", "openai/gpt-4o")
+    monkeypatch.setenv("LLM_API_KEY", "sk-test")
+    monkeypatch.setenv("LLM_TIMEOUT", "600")
+    monkeypatch.setenv("LLM_PREFLIGHT_TIMEOUT", "12")
+    _fresh_settings(monkeypatch, tmp_path)
+    seen: dict[str, Any] = {}
+
+    async def fake_request(_model: Any, **kwargs: Any) -> None:
+        seen.update(kwargs)
+
+    monkeypatch.setattr(scan_setup, "preflight_request", fake_request)
+    asyncio.run(preflight_model_connection("openai/gpt-4o", settings=load_settings()))
+    assert seen["timeout"] == 12
+    assert seen["model_name"] == "openai/gpt-4o"