diff --git a/src/s5p/pool.py b/src/s5p/pool.py
index f1d25d4..cc3b8fd 100644
--- a/src/s5p/pool.py
+++ b/src/s5p/pool.py
@@ -33,6 +33,7 @@ class ProxyEntry:
     last_seen: float = 0.0
     last_ok: float = 0.0
     last_test: float = 0.0
+    last_fail: float = 0.0
     fails: int = 0
     tests: int = 0
     alive: bool = False
@@ -96,13 +97,25 @@ class ProxyPool:
         key = random.choices(self._alive_keys, weights=weights)[0]
         return self._proxies[key].hop
 
+    def report_failure(self, hop: ChainHop) -> None:
+        """Record a connection-time failure for a proxy."""
+        key = f"{hop.proto}://{hop.host}:{hop.port}"
+        entry = self._proxies.get(key)
+        if entry:
+            entry.last_fail = time.time()
+
     @staticmethod
     def _weight(entry: ProxyEntry, now: float) -> float:
-        """Compute selection weight from recency of last success."""
+        """Compute selection weight from recency and failure backoff."""
         if entry.last_ok <= 0:
             return 0.01
         age = now - entry.last_ok
-        return 1.0 / (1.0 + age / 300.0)
+        w = 1.0 / (1.0 + age / 300.0)
+        # penalize proxies that failed since their last health-test success
+        if entry.last_fail >= entry.last_ok:
+            fail_age = now - entry.last_fail
+            w *= min(fail_age / 60.0, 1.0)  # ramp back over 60s
+        return max(w, 0.01)
 
     @property
     def count(self) -> int:
@@ -355,6 +368,7 @@ class ProxyPool:
                     hop=hop,
                     last_seen=entry.get("last_seen", 0.0),
                     last_ok=entry.get("last_ok", 0.0),
+                    last_fail=entry.get("last_fail", 0.0),
                     fails=entry.get("fails", 0),
                     tests=entry.get("tests", 0),
                     alive=entry.get("alive", False),
@@ -383,6 +397,7 @@ class ProxyPool:
                 "password": entry.hop.password,
                 "last_seen": entry.last_seen,
                 "last_ok": entry.last_ok,
+                "last_fail": entry.last_fail,
                 "fails": entry.fails,
                 "tests": entry.tests,
                 "alive": entry.alive,
diff --git a/src/s5p/server.py b/src/s5p/server.py
index 5f243ff..406d6d5 100644
--- a/src/s5p/server.py
+++ b/src/s5p/server.py
@@ -103,11 +103,12 @@ async def _handle_client(
 
         for attempt in range(attempts):
             effective_chain = list(config.chain)
+            pool_hop = None
             if proxy_pool:
-                hop = await proxy_pool.get()
-                if hop:
-                    effective_chain.append(hop)
-                    logger.debug("[%s] +proxy %s", tag, hop)
+                pool_hop = await proxy_pool.get()
+                if pool_hop:
+                    effective_chain.append(pool_hop)
+                    logger.debug("[%s] +proxy %s", tag, pool_hop)
 
             try:
                 t0 = time.monotonic()
@@ -119,6 +120,8 @@ async def _handle_client(
                 break
             except (ProtoError, asyncio.TimeoutError, ConnectionError, OSError) as e:
                 last_err = e
+                if pool_hop and isinstance(proxy_pool, ProxyPool):
+                    proxy_pool.report_failure(pool_hop)
                 if metrics:
                     metrics.retries += 1
                 if attempt + 1 < attempts:
diff --git a/tests/test_pool.py b/tests/test_pool.py
index 131ed59..97b0e39 100644
--- a/tests/test_pool.py
+++ b/tests/test_pool.py
@@ -116,6 +116,42 @@ class TestProxyPoolWeight:
         entry.last_ok = 0
         assert ProxyPool._weight(entry, now) == pytest.approx(0.01)
 
+    def test_weight_failure_penalty(self):
+        hop = ChainHop(proto="socks5", host="1.2.3.4", port=1080)
+        now = 1000.0
+
+        # healthy proxy: weight ~1.0
+        entry = ProxyEntry(hop=hop, last_ok=now)
+        assert ProxyPool._weight(entry, now) == pytest.approx(1.0)
+
+        # just failed: weight drops to floor (fail_age=0 -> multiplier=0)
+        entry.last_fail = now
+        assert ProxyPool._weight(entry, now) == pytest.approx(0.01)
+
+        # 30s after failure: base=1/(1+30/300)=0.909, penalty=30/60=0.5 -> ~0.45
+        assert ProxyPool._weight(entry, now + 30) == pytest.approx(0.4545, abs=0.05)
+
+        # 60s after failure: penalty=1.0, only base decay -> 1/(1+60/300)=0.833
+        assert ProxyPool._weight(entry, now + 60) == pytest.approx(0.833, abs=0.05)
+
+    def test_report_failure(self):
+        cfg = ProxyPoolConfig(sources=[])
+        pool = ProxyPool(cfg, [], timeout=10.0)
+        hop = ChainHop(proto="socks5", host="1.2.3.4", port=1080)
+        pool._proxies["socks5://1.2.3.4:1080"] = ProxyEntry(
+            hop=hop, alive=True, last_ok=time.time(),
+        )
+
+        assert pool._proxies["socks5://1.2.3.4:1080"].last_fail == 0.0
+        pool.report_failure(hop)
+        assert pool._proxies["socks5://1.2.3.4:1080"].last_fail > 0.0
+
+    def test_report_failure_unknown_proxy(self):
+        cfg = ProxyPoolConfig(sources=[])
+        pool = ProxyPool(cfg, [], timeout=10.0)
+        hop = ChainHop(proto="socks5", host="9.9.9.9", port=1080)
+        pool.report_failure(hop)  # should not raise
+
 
 class TestProxyPoolFetchFile:
     """Test file source parsing."""