diff --git a/pyicloud/base.py b/pyicloud/base.py
index 8e3ca2b6..9e2714ee 100644
--- a/pyicloud/base.py
+++ b/pyicloud/base.py
@@ -31,6 +31,7 @@
     PyiCloud2FARequiredException,
     PyiCloudAcceptTermsException,
     PyiCloudAPIResponseException,
+    PyiCloudConnectionException,
     PyiCloudFailedLoginException,
     PyiCloudNoTrustedNumberAvailable,
     PyiCloudPasswordException,
@@ -636,6 +637,9 @@ def _srp_authentication(self, pause_2fa: bool = False) -> bool:
                 headers=self._get_auth_headers(),
             )
             response.raise_for_status()
+        except PyiCloudConnectionException:
+            # Not a credentials problem; let it through as itself.
+            raise
         except (
             PyiCloudAPIResponseException,
             HTTPError,
@@ -697,6 +701,9 @@ def _srp_authentication(self, pause_2fa: bool = False) -> bool:
                 PyiCloudNoTrustedNumberAvailable,
             ) as error:
                 LOGGER.debug("Automatic 2FA code delivery failed: %s", error)
+        except PyiCloudConnectionException:
+            # Not a credentials problem; let it through as itself.
+            raise
         except PyiCloudAPIResponseException as error:
             msg = "Invalid email/password combination."
             raise PyiCloudFailedLoginException(msg) from error
@@ -755,6 +762,9 @@ def _authenticate_with_token(self, require_trust: bool = True) -> None:
             self._hsa2_boot_context = None
             self._clear_trusted_device_bridge_state()
             self._set_two_factor_delivery_state("unknown")
+        except PyiCloudConnectionException:
+            # Not a credentials problem; let it through as itself.
+            raise
         except (PyiCloudAPIResponseException, HTTPError) as error:
             msg = "Invalid authentication token."
             raise PyiCloudFailedLoginException(msg, error) from error
@@ -773,6 +783,9 @@ def _authenticate_with_credentials_service(self, service: str | None) -> None:
             self._handle_accept_terms(login_data)
 
             self.data = self._validate_token()
+        except PyiCloudConnectionException:
+            # Not a credentials problem; let it through as itself.
+            raise
         except PyiCloudAPIResponseException as error:
             msg = "Invalid email/password combination."
             raise PyiCloudFailedLoginException(msg, error) from error
@@ -1261,6 +1274,9 @@ def validate_2fa_code(self, code: str) -> bool:
                 self._validate_trusted_device_code(code)
         except PyiCloudTrustedDeviceVerificationException:
             raise
+        except PyiCloudConnectionException:
+            # Never seen by Apple, so it says nothing about the code.
+            raise
         except PyiCloudAPIResponseException:
             # Wrong verification code
             LOGGER.error("Code verification failed.")
@@ -1320,6 +1336,9 @@ def trust_session(self) -> bool:
             self._authenticate_with_token()
             LOGGER.debug("Session trust successful.")
             return True
+        except PyiCloudConnectionException:
+            # Apple never answered, so the session was not refused.
+            raise
         except (PyiCloudAPIResponseException, PyiCloud2FARequiredException):
             LOGGER.error("Session trust failed.")
             return False
diff --git a/pyicloud/exceptions.py b/pyicloud/exceptions.py
index 2a498fc7..7714d495 100644
--- a/pyicloud/exceptions.py
+++ b/pyicloud/exceptions.py
@@ -57,6 +57,26 @@ class PyiCloudPCSTimeoutException(PyiCloudAPIResponseException):
     """Raised when PCS access could not be granted after all retries."""
 
 
+class PyiCloudConnectionException(PyiCloudAPIResponseException):
+    """Raised when iCloud could not be reached at all.
+
+    A connection error, DNS failure or timeout says nothing about whether the
+    caller's credentials or session are still good, only that no answer came
+    back. Callers need to tell the two apart because the remedies are opposite:
+    a rejected password is fixed by asking the user to log in again, while an
+    unreachable service is fixed by waiting and retrying.
+
+    Distinguishing it matters most during authentication, where every transport
+    failure used to be reported as a failed login. A consumer acting on that
+    asks the user to re-enter working credentials in the middle of an outage,
+    and, if it stops polling until they do, stays down long after iCloud has
+    come back.
+
+    Subclasses the generic response error so existing handlers keep catching
+    it, and carries no ``code`` because no HTTP response was received.
+    """
+
+
 class PyiCloudEndpointGoneException(PyiCloudAPIResponseException):
     """Raised when Apple reports an endpoint as permanently gone (HTTP 410).
 
diff --git a/pyicloud/session.py b/pyicloud/session.py
index eb6e6132..8cbdddea 100644
--- a/pyicloud/session.py
+++ b/pyicloud/session.py
@@ -28,6 +28,7 @@
     PyiCloud2SARequiredException,
     PyiCloudAPIResponseException,
     PyiCloudAuthRequiredException,
+    PyiCloudConnectionException,
     PyiCloudEndpointGoneException,
     PyiCloudServiceNotActivatedException,
 )
@@ -376,7 +377,9 @@ def _raise_request_exception(err: requests.exceptions.RequestException) -> NoRet
                 reason=err.response.text,
                 code=err.response.status_code,
             ) from err
-        raise PyiCloudAPIResponseException("Request failed to iCloud") from err
+        # No response came back at all, so this is a connection error rather
+        # than anything iCloud said about the request.
+        raise PyiCloudConnectionException("Request failed to iCloud") from err
 
     def _handle_request_error(
         self,
diff --git a/tests/test_base.py b/tests/test_base.py
index 0c2eb4ad..0eed647f 100644
--- a/tests/test_base.py
+++ b/tests/test_base.py
@@ -25,6 +25,7 @@
     PyiCloud2SARequiredException,
     PyiCloudAcceptTermsException,
     PyiCloudAPIResponseException,
+    PyiCloudConnectionException,
     PyiCloudEndpointGoneException,
     PyiCloudFailedLoginException,
     PyiCloudPCSTimeoutException,
@@ -3283,6 +3284,92 @@ def test_authenticate_with_token_require_trust_true_raises_for_paused_session(
         pyicloud_service._authenticate_with_token(require_trust=True)
 
 
+def test_authenticate_with_token_keeps_connection_failure_distinct(
+    pyicloud_service: PyiCloudService, monkeypatch: pytest.MonkeyPatch
+) -> None:
+    """An unreachable iCloud must not be reported as a failed login.
+
+    Callers act on the difference: a rejected password is fixed by asking the
+    user to log in again, an outage by retrying later.
+    """
+    monkeypatch.setattr(
+        pyicloud_service.session,
+        "post",
+        MagicMock(side_effect=PyiCloudConnectionException("Request failed to iCloud")),
+    )
+    pyicloud_service.session._data = {
+        "session_token": "a-token",
+        "account_country": "USA",
+        "trust_token": "",
+    }
+
+    with pytest.raises(PyiCloudConnectionException):
+        pyicloud_service._authenticate_with_token()
+
+
+def test_authenticate_with_token_still_reports_rejected_token(
+    pyicloud_service: PyiCloudService, monkeypatch: pytest.MonkeyPatch
+) -> None:
+    """An answer from iCloud rejecting the token is still a failed login."""
+    monkeypatch.setattr(
+        pyicloud_service.session,
+        "post",
+        MagicMock(
+            side_effect=PyiCloudAPIResponseException("Authentication required", 421)
+        ),
+    )
+    pyicloud_service.session._data = {
+        "session_token": "a-token",
+        "account_country": "USA",
+        "trust_token": "",
+    }
+
+    with pytest.raises(PyiCloudFailedLoginException):
+        pyicloud_service._authenticate_with_token()
+
+
+def test_validate_2fa_code_does_not_blame_the_code_for_an_outage(
+    pyicloud_service: PyiCloudService, monkeypatch: pytest.MonkeyPatch
+) -> None:
+    """An unreachable iCloud must not come back as a wrong verification code."""
+    monkeypatch.setattr(
+        pyicloud_service,
+        "_validate_trusted_device_code",
+        MagicMock(side_effect=PyiCloudConnectionException("Request failed to iCloud")),
+    )
+    monkeypatch.setattr(
+        type(pyicloud_service),
+        "two_factor_delivery_method",
+        property(lambda _self: "trusted_device"),
+    )
+
+    with pytest.raises(PyiCloudConnectionException):
+        pyicloud_service.validate_2fa_code("123456")
+
+
+def test_trust_session_does_not_report_refusal_for_an_outage(
+    pyicloud_service: PyiCloudService, monkeypatch: pytest.MonkeyPatch
+) -> None:
+    """An unreachable iCloud must not come back as a refused session trust."""
+    monkeypatch.setattr(
+        pyicloud_service.session,
+        "get",
+        MagicMock(side_effect=PyiCloudConnectionException("Request failed to iCloud")),
+    )
+
+    with pytest.raises(PyiCloudConnectionException):
+        pyicloud_service.trust_session()
+
+
+def test_connection_exception_is_still_an_api_response_exception() -> None:
+    """Existing handlers must keep catching it."""
+    error = PyiCloudConnectionException("Request failed to iCloud")
+
+    assert isinstance(error, PyiCloudAPIResponseException)
+    # No response came back, so there is no status to report.
+    assert error.code is None
+
+
 def test_srp_authentication_pause_2fa_includes_pause2fa_flag(
     pyicloud_service: PyiCloudService,
 ) -> None: