diff --git a/.sampo/changesets/flags-no-retry-connection-refused.md b/.sampo/changesets/flags-no-retry-connection-refused.md
new file mode 100644
index 000000000..e5a465d32
--- /dev/null
+++ b/.sampo/changesets/flags-no-retry-connection-refused.md
@@ -0,0 +1,5 @@
+---
+pypi/posthog: patch
+---
+
+Stop retrying `/flags` requests when the connection is refused, so the flag error surfaces right away instead of after the retry backoff.
diff --git a/posthog/request.py b/posthog/request.py
index 03316fc1f..52854f922 100644
--- a/posthog/request.py
+++ b/posthog/request.py
@@ -15,6 +15,7 @@
 import requests
 from requests.adapters import HTTPAdapter
 from urllib3.connection import HTTPConnection
+from urllib3.exceptions import NewConnectionError
 from urllib3.util.retry import Retry
 
 from posthog._logging import _configure_posthog_logging
@@ -322,6 +323,29 @@ def _process_response(
         raise APIError(res.status_code, res.text, retry_after=retry_after)
 
 
+def _is_connection_refused(exc: BaseException) -> bool:
+    """Return True when a requests transport error wraps a refused connection."""
+    pending: List[Any] = [exc]
+    seen = set()
+    while pending:
+        current = pending.pop()
+        if current is None or id(current) in seen:
+            continue
+        seen.add(id(current))
+        if isinstance(current, ConnectionRefusedError):
+            return True
+        if isinstance(current, BaseException):
+            pending.extend(current.args)
+            pending.append(current.__cause__)
+            # __context__ records whatever exception was being handled, which may
+            # have nothing to do with this request. urllib3 1.x only links the
+            # socket error to NewConnectionError that way, so follow it just there.
+            if isinstance(current, NewConnectionError):
+                pending.append(current.__context__)
+        pending.append(getattr(current, "reason", None))
+    return False
+
+
 def _feature_flags_retry_delay(failed_attempt: int) -> float:
     return _FEATURE_FLAGS_RETRY_BACKOFF_SECONDS * (2**failed_attempt)
 
@@ -354,8 +378,12 @@ def flags(
             return _process_response(
                 res, success_message="Feature flags evaluated successfully"
             )
-        except (requests.exceptions.ConnectionError, requests.exceptions.Timeout):
-            if failed_attempt >= retries:
+        except (
+            requests.exceptions.ConnectionError,
+            requests.exceptions.Timeout,
+        ) as exc:
+            # A refused connection is not transient, so it is not retried.
+            if failed_attempt >= retries or _is_connection_refused(exc):
                 raise
         except APIError as exc:
             if (
diff --git a/posthog/test/test_request.py b/posthog/test/test_request.py
index e23b0a446..d9d44df79 100644
--- a/posthog/test/test_request.py
+++ b/posthog/test/test_request.py
@@ -1,5 +1,6 @@
 import gzip
 import json
+import socket
 import unittest
 import zlib
 from datetime import date, datetime, timedelta
@@ -702,6 +703,60 @@ def test_flags_retries_transport_errors_once_by_default(
         self.assertEqual(mock_session.post.call_count, 2)
         mock_sleep.assert_called_once_with(0.3)
 
+    @mock.patch("posthog.request.time.sleep")
+    def test_flags_does_not_retry_refused_connection(self, mock_sleep):
+        # Bind and close a socket so the port refuses connections.
+        with socket.socket(socket.AF_INET, socket.SOCK_STREAM) as sock:
+            sock.bind(("127.0.0.1", 0))
+            port = sock.getsockname()[1]
+
+        with mock.patch("posthog.request.post", wraps=request_module.post) as mock_post:
+            with self.assertRaises(requests.exceptions.ConnectionError):
+                flags(
+                    "test-key",
+                    f"http://127.0.0.1:{port}",
+                    max_retries=2,
+                    distinct_id="user123",
+                )
+
+        self.assertEqual(mock_post.call_count, 1)
+        mock_sleep.assert_not_called()
+
+    @mock.patch("posthog.request.time.sleep")
+    @mock.patch("posthog.request._get_flags_session")
+    def test_flags_retries_when_handling_an_unrelated_refused_connection(
+        self, mock_get_flags_session, mock_sleep
+    ):
+        mock_response = requests.Response()
+        mock_response.status_code = 200
+        mock_response._content = json.dumps(
+            {
+                "featureFlags": {"test-flag": True},
+                "featureFlagPayloads": {},
+                "errorsWhileComputingFlags": False,
+            }
+        ).encode("utf-8")
+
+        mock_session = mock.MagicMock()
+        mock_session.post.side_effect = [
+            requests.exceptions.Timeout("timed out"),
+            mock_response,
+        ]
+        mock_get_flags_session.return_value = mock_session
+
+        # The application evaluates flags while handling its own refused
+        # connection, so the timeout inherits that error as its __context__.
+        try:
+            raise ConnectionRefusedError("database is down")
+        except ConnectionRefusedError:
+            response = flags(
+                "test-key", "https://test.posthog.com", distinct_id="user123"
+            )
+
+        self.assertEqual(response["featureFlags"], {"test-flag": True})
+        self.assertEqual(mock_session.post.call_count, 2)
+        mock_sleep.assert_called_once_with(0.3)
+
     @mock.patch("posthog.request.time.sleep")
     @mock.patch("posthog.request._get_flags_session")
     def test_flags_retry_count_zero_disables_retries(