diff --git a/homeassistant/components/smtp/notify.py b/homeassistant/components/smtp/notify.py
index c17753de588f..be9fb367b5f1 100644
--- a/homeassistant/components/smtp/notify.py
+++ b/homeassistant/components/smtp/notify.py
@@ -40,11 +40,7 @@ from homeassistant.const import (
 )
 from homeassistant.core import HomeAssistant
 from homeassistant.data_entry_flow import FlowResultType
-from homeassistant.exceptions import (
-    ConfigEntryAuthFailed,
-    HomeAssistantError,
-    ServiceValidationError,
-)
+from homeassistant.exceptions import HomeAssistantError, ServiceValidationError
 from homeassistant.helpers import config_validation as cv, entity_registry as er
 from homeassistant.helpers.device_registry import DeviceEntryType, DeviceInfo
 from homeassistant.helpers.entity_platform import AddConfigEntryEntitiesCallback
@@ -325,7 +321,8 @@ class MailNotifyEntity(NotifyEntity):
                     await client.send_message(msg)
                 break
             except aiosmtplib.SMTPAuthenticationError as e:
-                raise ConfigEntryAuthFailed(
+                self._entry.async_start_reauth(self.hass)
+                raise HomeAssistantError(
                     translation_domain=DOMAIN,
                     translation_key="authentication_error",
                 ) from e
diff --git a/tests/components/smtp/test_notify.py b/tests/components/smtp/test_notify.py
index 529ea2a58c43..8132cd396e1c 100644
--- a/tests/components/smtp/test_notify.py
+++ b/tests/components/smtp/test_notify.py
@@ -6,7 +6,10 @@ import re
 from smtplib import SMTPException, SMTPServerDisconnected
 from unittest.mock import AsyncMock, MagicMock, patch
 
-import aiosmtplib
+from aiosmtplib import (
+    SMTPAuthenticationError,
+    SMTPException as aiosmtplib_SMTPException,
+)
 import pytest
 from syrupy.assertion import SnapshotAssertion
 
@@ -29,7 +32,7 @@ from homeassistant.components.smtp.const import (
     DOMAIN,
 )
 from homeassistant.components.smtp.notify import MailNotificationService
-from homeassistant.config_entries import ConfigEntryState
+from homeassistant.config_entries import SOURCE_REAUTH, ConfigEntryState
 from homeassistant.const import ATTR_ENTITY_ID, CONF_NAME, CONF_RECIPIENT, STATE_UNKNOWN
 from homeassistant.core import HomeAssistant
 from homeassistant.exceptions import HomeAssistantError, ServiceValidationError
@@ -266,8 +269,8 @@ async def test_notify_send_message(
 @pytest.mark.parametrize(
     ("exception", "translation_key", "call_count"),
     [
-        (aiosmtplib.SMTPAuthenticationError(0, ""), "authentication_error", 1),
-        (aiosmtplib.SMTPException(""), "send_mail_connection_error", 2),
+        (SMTPAuthenticationError(0, ""), "authentication_error", 1),
+        (aiosmtplib_SMTPException(""), "send_mail_connection_error", 2),
     ],
 )
 @pytest.mark.usefixtures("make_msgid", "smtp")
@@ -305,6 +308,48 @@ async def test_notify_send_message_exceptions(
     assert aiosmtplib.__aenter__.return_value.send_message.call_count == call_count
 
 
+@pytest.mark.usefixtures("make_msgid", "smtp")
+async def test_notify_send_message_reauth_flow(
+    hass: HomeAssistant,
+    config_entry: MockConfigEntry,
+    aiosmtplib: AsyncMock,
+) -> None:
+    """Test authentication error starts reauth flow."""
+
+    config_entry.add_to_hass(hass)
+    await hass.config_entries.async_setup(config_entry.entry_id)
+    await hass.async_block_till_done()
+
+    assert config_entry.state is ConfigEntryState.LOADED
+
+    aiosmtplib.__aenter__.return_value.send_message.side_effect = (
+        SMTPAuthenticationError(0, "")
+    )
+
+    with pytest.raises(HomeAssistantError) as e:
+        await hass.services.async_call(
+            NOTIFY_DOMAIN,
+            SERVICE_SEND_MESSAGE,
+            {
+                ATTR_ENTITY_ID: "notify.home_assistant_recipient",
+                ATTR_MESSAGE: "Hello World",
+            },
+            blocking=True,
+        )
+
+    assert e.value.translation_key == "authentication_error"
+    assert aiosmtplib.__aenter__.return_value.send_message.call_count == 1
+
+    flows = hass.config_entries.flow.async_progress()
+    assert len(flows) == 1
+
+    flow = flows[0]
+    assert flow["step_id"] == "reauth_confirm"
+    assert flow["handler"] == DOMAIN
+    assert flow["context"]["source"] == SOURCE_REAUTH
+    assert flow["context"]["entry_id"] == config_entry.entry_id
+
+
 @pytest.mark.parametrize("exception", [SMTPServerDisconnected, SMTPException])
 @pytest.mark.usefixtures("aiosmtplib")
 async def test_legacy_notify_exception(