diff --git a/backend/apps/web/web.py b/backend/apps/web/web.py
index b756ec23..488dd7e6 100644
--- a/backend/apps/web/web.py
+++ b/backend/apps/web/web.py
@@ -215,10 +215,18 @@ async def search(body: SearchBody) -> Dict:
 
     async def try_keyless_engines() -> Optional[Dict]:
         outcome = await race_keyless(
+            # Order is quality, not alphabet: race_keyless starts these in sequence and only hedges
+            # the next one in if the leader stalls, so whoever sits second inherits every ddg
+            # challenge. Measured 2026-08-13, N=22 fact queries, 12s pacing so nobody is being read
+            # through their own rate limiter: ddg 21/22 (0.955), bing 6/22 (0.273), brave 2/2 of the
+            # 2 it served before throttling, startpage 0/22. Bing answers something 100% of the time
+            # and answers CORRECTLY about a quarter of it, which is the worst shape for a silent
+            # fallback, so it goes last. The dead rungs cost nothing: record_tier_failure cools them
+            # out after their first miss.
             [KeylessEngine(name="ddg", run=try_keyless),
-             KeylessEngine(name="bing", run=try_bing),
              KeylessEngine(name="brave", run=try_brave),
-             KeylessEngine(name="startpage", run=try_startpage)],
+             KeylessEngine(name="startpage", run=try_startpage),
+             KeylessEngine(name="bing", run=try_bing)],
             KEYLESS_TIER_SECONDS,
         )
         keyless_errors.extend(outcome.errors)
diff --git a/backend/tests/test_web_search_cascade.py b/backend/tests/test_web_search_cascade.py
index e174578f..f68c3322 100644
--- a/backend/tests/test_web_search_cascade.py
+++ b/backend/tests/test_web_search_cascade.py
@@ -20,6 +20,7 @@ from backend.tests.web_cascade_fixtures import (  # noqa: F401
     allow_urls,
     bing_refuses,
     bing_returns,
+    brave_refuses,
     brave_returns,
     fresh_breaker,
     patch_browser_bridge,
@@ -210,15 +211,31 @@ async def test_bing_rescues_a_ddg_challenge_before_any_paid_backend(monkeypatch)
 
 
 @pytest.mark.asyncio
-async def test_brave_rescues_when_ddg_and_bing_both_refuse(monkeypatch):
+async def test_brave_rescues_when_ddg_refuses(monkeypatch):
+    """Brave now sits directly behind ddg, so it is what catches a ddg challenge."""
     ddg_throttled(monkeypatch)
-    bing_refuses(monkeypatch)
     brave_returns(monkeypatch, "[1] Independent index\n    https://brave-hit.example")
 
     res = await search(SearchBody(query="x"))
     assert res["backend"] == "brave"
     assert "brave-hit.example" in res["results"]
-    assert any("Bing" in e for e in res["cascade_errors"])
+
+
+@pytest.mark.asyncio
+async def test_bing_is_the_last_keyless_resort(monkeypatch):
+    """Bing answers something ~100% of the time and answers CORRECTLY ~27% (N=22, 12s pacing,
+    2026-08-13) against ddg's 95.5%, which is the worst possible shape for a silent fallback: the
+    caller cannot tell a good answer from an off-topic one. So it must serve only when every better
+    rung has declined, and that ordering is what this pins."""
+    ddg_throttled(monkeypatch)
+    brave_returns(monkeypatch, "[1] Brave result\n    https://brave-hit.example")
+    bing_returns(monkeypatch, "[1] Bing result\n    https://bing-hit.example")
+
+    res = await search(SearchBody(query="x"))
+    assert res["backend"] == "brave", (
+        f"bing served while brave was also answering, so it is not last: got {res['backend']}"
+    )
+    assert "bing-hit.example" not in res["results"]
 
 
 @pytest.mark.asyncio