diff --git a/pyproject.toml b/pyproject.toml
index b5af503..87cec2d 100644
--- a/pyproject.toml
+++ b/pyproject.toml
@@ -26,7 +26,7 @@ repository = "https://github.com/puddly/serialx"
 documentation = "https://puddly.github.io/serialx/"
 
 [project.optional-dependencies]
-esphome = ["aioesphomeapi>=46.12.0; python_version >= '3.11'"]
+esphome = ["aioesphomeapi>=46.21.0; python_version >= '3.11'"]
 
 [dependency-groups]
 dev = [
@@ -49,7 +49,7 @@ dev = [
   "types-pywin32>=311.0.0.20260508",
   "types-setuptools>=82.0.0.20260508",
   "setuptools-rust>=1.7.0",
-  "aioesphomeapi>=46.12.0 ; python_version >= '3.11'",
+  "aioesphomeapi>=46.21.0 ; python_version >= '3.11'",
 ]
 docs = [
   "sphinx>=7,<8.2.3; python_version < '3.11'",
diff --git a/serialx/platforms/serial_esphome.py b/serialx/platforms/serial_esphome.py
index f13c6cb..400458b 100644
--- a/serialx/platforms/serial_esphome.py
+++ b/serialx/platforms/serial_esphome.py
@@ -39,8 +39,15 @@
 from aioesphomeapi.client import MIN_VERSION_PROXY_ACK, APIClient
 from aioesphomeapi.core import (  # type: ignore[attr-defined]
     APIConnectionError,
+    ConnectionNotEstablishedAPIError,
+    HandshakeAPIError,
+    PingFailedAPIError,
     PingRequest,
     PingResponse,
+    ReadFailedAPIError,
+    ResolveAPIError,
+    ResolveTimeoutAPIError,
+    SocketAPIError,
     TimeoutAPIError,
 )
 from aioesphomeapi.model import (
@@ -212,9 +219,27 @@ def translate_esphome_errors(
     async def wrapper(*args: _P.args, **kwargs: _P.kwargs) -> _T:
         try:
             return await func(*args, **kwargs)
-        except TimeoutAPIError as exc:
+        except (TimeoutAPIError, ResolveTimeoutAPIError) as exc:
             raise TimeoutError(str(exc)) from exc
+        except (
+            ConnectionNotEstablishedAPIError,
+            SocketAPIError,
+            ResolveAPIError,
+            ReadFailedAPIError,
+            PingFailedAPIError,
+        ) as exc:
+            raise ConnectionError(str(exc)) from exc
         except APIConnectionError as exc:
+            # A clean disconnect (device reboot, `api.disconnect()`) fails pending
+            # requests with the bare base class.
+            if type(exc) is APIConnectionError:
+                raise ConnectionError(str(exc)) from exc
+
+            # A socket error mid-handshake is wrapped in the bare `HandshakeAPIError`,
+            # unlike its subclasses, which report encryption misconfiguration.
+            if type(exc) is HandshakeAPIError and isinstance(exc.__cause__, OSError):
+                raise ConnectionError(str(exc)) from exc
+
             raise SerialException(str(exc)) from exc
 
     return cast(Callable[_P, Coroutine[Any, Any, _T]], wrapper)
@@ -1215,7 +1240,7 @@ async def _connect(
         # Nothing is replayed for a connection that closed while we were setting
         # up, so the state has to be re-checked once the callback is installed.
         if not self._serial._api.is_connected:
-            raise SerialException("ESPHome API connection closed while connecting")
+            raise ConnectionError("ESPHome API connection closed while connecting")
 
         await self._serial._async_configure_port()
 
diff --git a/tests/test_serial_esphome.py b/tests/test_serial_esphome.py
index 45b2dae..87d77de 100644
--- a/tests/test_serial_esphome.py
+++ b/tests/test_serial_esphome.py
@@ -20,6 +20,25 @@
 import urllib.parse
 import warnings
 
+from aioesphomeapi.core import (
+    APIConnectionError,
+    BadMACAddressAPIError,
+    BadNameAPIError,
+    ConnectionNotEstablishedAPIError,
+    EncryptionHelloAPIError,
+    HandshakeAPIError,
+    InvalidAuthAPIError,
+    InvalidEncryptionKeyAPIError,
+    PingFailedAPIError,
+    ProtocolAPIError,
+    ReadFailedAPIError,
+    RequiresEncryptionAPIError,
+    ResolveAPIError,
+    ResolveTimeoutAPIError,
+    SocketAPIError,
+    SocketClosedAPIError,
+    TimeoutAPIError,
+)
 from aioesphomeapi.model import (
     APIVersion,
     DeviceInfo,
@@ -44,6 +63,7 @@
     async_serial_for_url,
     create_serial_connection,
     list_serial_ports,
+    open_serial_connection,
     redact_uri,
     udev_serial_by_id_stem,
 )
@@ -341,6 +361,131 @@ async def test_connect_timeout_raises_timeout_error() -> None:
                 pass
 
 
+@pytest.mark.parametrize("connection_exists", [False, True])
+async def test_open_disconnected_api_raises_connection_error(
+    connection_exists: bool,
+) -> None:
+    """An offline externally managed API is an I/O failure callers can retry."""
+    api = APIClient(address="127.0.0.1", port=ESPHOME_DEFAULT_PORT, password=None)
+    if connection_exists:
+        await api.start_resolve_host(log_errors=False)
+
+    with pytest.raises(
+        ConnectionError, match="Not connected|Authenticated connection not ready"
+    ) as exc_info:
+        await open_serial_connection(
+            url=None,
+            transport_cls=ESPHomeSerialTransport,
+            api=api,
+            port_name="test",
+            baudrate=115200,
+        )
+
+    assert isinstance(exc_info.value.__cause__, ConnectionNotEstablishedAPIError)
+    assert not api.is_connected
+
+
+@pytest.mark.parametrize(
+    ("error", "expected_type"),
+    [
+        (APIConnectionError("Connection closed"), ConnectionError),
+        (ConnectionNotEstablishedAPIError("Not ready"), ConnectionError),
+        (SocketAPIError("Connection refused"), ConnectionError),
+        (SocketClosedAPIError("Connection closed"), ConnectionError),
+        (ResolveAPIError("Host unavailable"), ConnectionError),
+        (ReadFailedAPIError("Read failed"), ConnectionError),
+        (PingFailedAPIError("Ping failed"), ConnectionError),
+        (TimeoutAPIError("Connect timed out"), TimeoutError),
+        (ResolveTimeoutAPIError("Resolve timed out"), TimeoutError),
+        (InvalidAuthAPIError("Invalid password"), SerialException),
+        (InvalidEncryptionKeyAPIError("Invalid key"), SerialException),
+        (HandshakeAPIError("Invalid handshake"), SerialException),
+        (ProtocolAPIError("Invalid protocol"), SerialException),
+        (RequiresEncryptionAPIError("Encryption required"), SerialException),
+        (BadNameAPIError("Wrong device", "other-device"), SerialException),
+        (
+            BadMACAddressAPIError("Wrong device", "other-device", "00:11:22:33:44:55"),
+            SerialException,
+        ),
+    ],
+)
+async def test_open_api_error_classification(
+    error: APIConnectionError, expected_type: type[Exception]
+) -> None:
+    """Opening preserves the distinction between transport and protocol failures."""
+    with patch.object(APIClient, "connect", side_effect=error):
+        with pytest.raises(expected_type) as exc_info:
+            await open_serial_connection(
+                url="esphome://127.0.0.1:6053?port_name=test", baudrate=115200
+            )
+
+    assert type(exc_info.value) is expected_type
+    assert exc_info.value.__cause__ is error
+
+
+@pytest.mark.parametrize(
+    ("error", "cause", "expected_type"),
+    [
+        (
+            HandshakeAPIError("Handshake failed"),
+            ConnectionResetError(),
+            ConnectionError,
+        ),
+        (HandshakeAPIError("Handshake failed"), ValueError(), SerialException),
+        # aioesphomeapi reports this as a likely encryption mismatch
+        (
+            EncryptionHelloAPIError("Dropped after hello"),
+            ConnectionResetError(),
+            SerialException,
+        ),
+        (
+            InvalidEncryptionKeyAPIError("Invalid key"),
+            ConnectionResetError(),
+            SerialException,
+        ),
+    ],
+)
+async def test_open_handshake_error_classification(
+    error: HandshakeAPIError, cause: Exception, expected_type: type[Exception]
+) -> None:
+    """Only a socket error wrapped in the bare `HandshakeAPIError` is retryable."""
+    error.__cause__ = cause
+
+    with patch.object(APIClient, "connect", side_effect=error):
+        with pytest.raises(expected_type) as exc_info:
+            await open_serial_connection(
+                url="esphome://127.0.0.1:6053?port_name=test", baudrate=115200
+            )
+
+    assert type(exc_info.value) is expected_type
+    assert exc_info.value.__cause__ is error
+
+
+async def test_open_api_disconnect_during_setup() -> None:
+    """A connection lost before setup completes is still an I/O failure."""
+    api = mock_api_client("test")
+    api.is_connected = True
+    unsub = MagicMock()
+
+    def disconnect_during_setup(*args: object) -> MagicMock:
+        api.is_connected = False
+        return unsub
+
+    api.subscribe_serial_proxy_data.side_effect = disconnect_during_setup
+
+    with pytest.raises(ConnectionError, match="closed while connecting"):
+        await open_serial_connection(
+            url=None,
+            transport_cls=ESPHomeSerialTransport,
+            api=api,
+            port_name="test",
+            baudrate=115200,
+        )
+
+    unsub.assert_called_once_with()
+    api.disconnect.assert_not_called()
+
+
 @pytest.mark.skipif(not ESPHOME_HOST_BINARY, reason="esphome host binary not available")
 async def test_noise_psk_key_alias() -> None:
     """Test that connecting without encryption to an encrypted server raises."""
@@ -770,6 +915,31 @@ async def subscribe(instance: int, *, timeout: float) -> None:
     await transport.wait_closed()
 
 
+async def test_flush_clean_disconnect_raises_connection_error() -> None:
+    """A device-initiated disconnect (e.g. reboot) fails a pending flush retryably."""
+    api = mock_api_client("Zigbee")
+    error = APIConnectionError("Connection closed")
+    api.attach_mock(AsyncMock(side_effect=error), "serial_proxy_flush")
+
+    transport, _ = await create_serial_connection(
+        asyncio.get_running_loop(),
+        asyncio.Protocol,
+        url=None,
+        baudrate=115200,
+        transport_cls=ESPHomeSerialTransport,
+        api=api,
+        port_name="Zigbee",
+    )
+
+    with pytest.raises(ConnectionError, match="Connection closed") as exc_info:
+        await transport.flush()
+
+    assert exc_info.value.__cause__ is error
+
+    transport.close()
+    await transport.wait_closed()
+
+
 async def test_mode_protocol_kwarg_with_external_api() -> None:
     """The `mode` kwarg is honored when the API client is passed in externally."""
     api = mock_api_client("Zigbee")
diff --git a/uv.lock b/uv.lock
index ca0bf81..f0c2e60 100644
--- a/uv.lock
+++ b/uv.lock
@@ -27,7 +27,7 @@ wheels = [
 
 [[package]]
 name = "aioesphomeapi"
-version = "46.12.0"
+version = "46.21.0"
 source = { registry = "https://pypi.org/simple" }
 dependencies = [
     { name = "aiohappyeyeballs" },
@@ -41,81 +41,92 @@ dependencies = [
     { name = "tzlocal" },
     { name = "zeroconf" },
 ]
-wheels = [
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+    { url = "https://files.pythonhosted.org/packages/b5/c0/cb9cec9decad292663cc6561cc084d0e49e7265243630b6907b1210cb81e/aioesphomeapi-46.21.0-cp315-cp315t-win_amd64.whl", hash = "sha256:f3d9a5cce4acc7bc729f768b1ca6ee62b7da4ca4dbeba43f2aaa4db889b1734e", size = 661094, upload-time = "2026-10-22T07:34:20.176Z" },
 ]
 
 [[package]]
@@ -1986,7 +1997,7 @@ docs = [
 
 [package.metadata]
 requires-dist = [
-    { name = "aioesphomeapi", marker = "python_full_version >= '3.11' and extra == 'esphome'", specifier = ">=46.12.0" },
+    { name = "aioesphomeapi", marker = "python_full_version >= '3.11' and extra == 'esphome'", specifier = ">=46.21.0" },
     { name = "async-timeout", marker = "python_full_version < '3.11'", specifier = ">=3.0.0" },
     { name = "pywin32", marker = "sys_platform == 'win32'" },
     { name = "typing-extensions", specifier = ">=4.13.0" },
@@ -1995,7 +2006,7 @@ provides-extras = ["esphome"]
 
 [package.metadata.requires-dev]
 dev = [
-    { name = "aioesphomeapi", marker = "python_full_version >= '3.11'", specifier = ">=46.12.0" },
+    { name = "aioesphomeapi", marker = "python_full_version >= '3.11'", specifier = ">=46.21.0" },
     { name = "async-timeout", specifier = ">=5.0.1" },
     { name = "codespell", specifier = ">=2.4.2" },
     { name = "mypy", specifier = ">=2.1.0" },