diff --git a/homeassistant/components/smtp/notify.py b/homeassistant/components/smtp/notify.py
index 4f887ae3b448..325f121575e3 100644
--- a/homeassistant/components/smtp/notify.py
+++ b/homeassistant/components/smtp/notify.py
@@ -315,25 +315,37 @@ class MailNotificationService(SmtpClient, BaseNotificationService):
     def _send_email(self, msg: MIMEMultipart | MIMEText, recipients: list[str]) -> None:
         """Send the message."""
         mail = self.connect()
-        for _ in range(self.tries):
+        for attempt in range(self.tries):
             try:
                 mail.sendmail(self._sender, recipients, msg.as_string())
                 break
-            except SMTPServerDisconnected:
+            except SMTPServerDisconnected as e:
+                with suppress(SMTPException):
+                    mail.quit()
+                if attempt == self.tries - 1:
+                    _LOGGER.debug("Full exception:", exc_info=True)
+                    raise HomeAssistantError(
+                        translation_domain=DOMAIN,
+                        translation_key="send_mail_connection_error",
+                    ) from e
                 _LOGGER.warning(
                     "SMTPServerDisconnected sending mail: retrying connection",
                     exc_info=_LOGGER.isEnabledFor(logging.DEBUG),
                 )
+                mail = self.connect()
+            except SMTPException as e:
                 with suppress(SMTPException):
                     mail.quit()
-                mail = self.connect()
-            except SMTPException:
+                if attempt == self.tries - 1:
+                    _LOGGER.debug("Full exception:", exc_info=True)
+                    raise HomeAssistantError(
+                        translation_domain=DOMAIN,
+                        translation_key="send_mail_connection_error",
+                    ) from e
                 _LOGGER.warning(
                     "SMTPException sending mail: retrying connection",
                     exc_info=_LOGGER.isEnabledFor(logging.DEBUG),
                 )
-                with suppress(SMTPException):
-                    mail.quit()
                 mail = self.connect()
         with suppress(SMTPException):
             mail.quit()
diff --git a/tests/components/smtp/test_notify.py b/tests/components/smtp/test_notify.py
index 3ebebfed260a..510013aa53a4 100644
--- a/tests/components/smtp/test_notify.py
+++ b/tests/components/smtp/test_notify.py
@@ -4,6 +4,7 @@ from pathlib import Path
 import re
 from smtplib import (
     SMTPAuthenticationError,
+    SMTPException,
     SMTPHeloError,
     SMTPSenderRefused,
     SMTPServerDisconnected,
@@ -16,6 +17,7 @@ from syrupy.assertion import SnapshotAssertion
 
 from homeassistant.components.notify import (
     ATTR_MESSAGE,
+    ATTR_TARGET,
     DOMAIN as NOTIFY_DOMAIN,
     SERVICE_SEND_MESSAGE,
 )
@@ -360,3 +362,35 @@ async def test_notify_retry_on_disconnect_with_broken_quit(
     )
 
     assert smtp.sendmail.call_count == 2
+
+
+@pytest.mark.parametrize("exception", [SMTPServerDisconnected, SMTPException])
+async def test_legacy_notify_exception(
+    hass: HomeAssistant,
+    config_entry: MockConfigEntry,
+    smtp: MagicMock,
+    exception: Exception,
+) -> None:
+    """Test legacy notify action raises when retries are exhausted."""
+
+    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
+
+    smtp.sendmail.side_effect = exception
+
+    with pytest.raises(HomeAssistantError) as e:
+        await hass.services.async_call(
+            NOTIFY_DOMAIN,
+            "home_assistant",
+            {
+                ATTR_TARGET: ["recipient@example.com"],
+                ATTR_MESSAGE: "Hello World",
+            },
+            blocking=True,
+        )
+
+    assert e.value.translation_key == "send_mail_connection_error"
+    assert smtp.sendmail.call_count == 2