diff --git a/homeassistant/components/alexa/config.py b/homeassistant/components/alexa/config.py
index 36f15735b8b..a22ebbcd30d 100644
--- a/homeassistant/components/alexa/config.py
+++ b/homeassistant/components/alexa/config.py
@@ -42,11 +42,11 @@ class AbstractConfig:
             self._unsub_proactive_report = self.hass.async_create_task(
                 async_enable_proactive_mode(self.hass, self)
             )
-        resp = await self._unsub_proactive_report
-
-        # Failed to start reporting.
-        if resp is None:
+        try:
+            await self._unsub_proactive_report
+        except Exception:  # pylint: disable=broad-except
             self._unsub_proactive_report = None
+            raise
 
     async def async_disable_proactive_mode(self):
         """Disable proactive mode."""
diff --git a/homeassistant/components/alexa/state_report.py b/homeassistant/components/alexa/state_report.py
index 4c11fb8c88c..022b38be59d 100644
--- a/homeassistant/components/alexa/state_report.py
+++ b/homeassistant/components/alexa/state_report.py
@@ -21,6 +21,9 @@ async def async_enable_proactive_mode(hass, smart_home_config):
 
     Proactive mode makes this component report state changes to Alexa.
     """
+    # Validate we can get access token.
+    await smart_home_config.async_get_access_token()
+
     async def async_entity_state_listener(changed_entity, old_state,
                                           new_state):
         if not new_state:
diff --git a/homeassistant/components/cloud/alexa_config.py b/homeassistant/components/cloud/alexa_config.py
index 746f01dd04b..aae48df9884 100644
--- a/homeassistant/components/cloud/alexa_config.py
+++ b/homeassistant/components/cloud/alexa_config.py
@@ -103,6 +103,15 @@ class AlexaConfig(alexa_config.AbstractConfig):
 
         if resp.status == 400:
             if body['reason'] in ('RefreshTokenNotFound', 'UnknownRegion'):
+                if self.should_report_state:
+                    await self._prefs.async_update(alexa_report_state=False)
+                    self.hass.components.persistent_notification.async_create(
+                        "There was an error reporting state to Alexa ({}). "
+                        "Please re-link your Alexa skill via the Alexa app to "
+                        "continue using it.".format(body['reason']),
+                        "Alexa state reporting disabled",
+                        "cloud_alexa_report",
+                    )
                 raise RequireRelink
 
             raise alexa_errors.NoTokenAvailable
@@ -200,6 +209,9 @@ class AlexaConfig(alexa_config.AbstractConfig):
         if not to_update and not to_remove:
             return True
 
+        # Make sure it's valid.
+        await self.async_get_access_token()
+
         tasks = []
 
         if to_update:
@@ -241,4 +253,7 @@ class AlexaConfig(alexa_config.AbstractConfig):
         elif action == 'remove' and self.should_expose(entity_id):
             to_remove.append(entity_id)
 
-        await self._sync_helper(to_update, to_remove)
+        try:
+            await self._sync_helper(to_update, to_remove)
+        except alexa_errors.NoTokenAvailable:
+            pass
diff --git a/homeassistant/components/cloud/client.py b/homeassistant/components/cloud/client.py
index 16a05b0d127..d22e5bf37ba 100644
--- a/homeassistant/components/cloud/client.py
+++ b/homeassistant/components/cloud/client.py
@@ -12,7 +12,10 @@ from homeassistant.components.google_assistant import smart_home as ga
 from homeassistant.helpers.typing import HomeAssistantType
 from homeassistant.helpers.dispatcher import async_dispatcher_send
 from homeassistant.util.aiohttp import MockRequest
-from homeassistant.components.alexa import smart_home as alexa_sh
+from homeassistant.components.alexa import (
+    smart_home as alexa_sh,
+    errors as alexa_errors,
+)
 
 from . import utils, alexa_config, google_config
 from .const import DISPATCHER_REMOTE_UPDATE
@@ -98,8 +101,14 @@ class CloudClient(Interface):
         """Initialize the client."""
         self.cloud = cloud
 
-        if self.alexa_config.should_report_state and self.cloud.is_logged_in:
+        if (not self.alexa_config.should_report_state or
+                not self.cloud.is_logged_in):
+            return
+
+        try:
             await self.alexa_config.async_enable_proactive_mode()
+        except alexa_errors.NoTokenAvailable:
+            pass
 
     async def cleanups(self) -> None:
         """Cleanup some stuff after logout."""
diff --git a/homeassistant/components/cloud/http_api.py b/homeassistant/components/cloud/http_api.py
index d9c4ddcf1ce..0cd08dd3d5f 100644
--- a/homeassistant/components/cloud/http_api.py
+++ b/homeassistant/components/cloud/http_api.py
@@ -14,7 +14,10 @@ from homeassistant.components.http.data_validator import (
     RequestDataValidator)
 from homeassistant.components import websocket_api
 from homeassistant.components.websocket_api import const as ws_const
-from homeassistant.components.alexa import entities as alexa_entities
+from homeassistant.components.alexa import (
+    entities as alexa_entities,
+    errors as alexa_errors,
+)
 from homeassistant.components.google_assistant import helpers as google_helpers
 
 from .const import (
@@ -375,6 +378,24 @@ async def websocket_update_prefs(hass, connection, msg):
     changes = dict(msg)
     changes.pop('id')
     changes.pop('type')
+
+    # If we turn alexa linking on, validate that we can fetch access token
+    if changes.get(PREF_ALEXA_REPORT_STATE):
+        try:
+            with async_timeout.timeout(10):
+                await cloud.client.alexa_config.async_get_access_token()
+        except asyncio.TimeoutError:
+            connection.send_error(msg['id'], 'alexa_timeout',
+                                  'Timeout validating Alexa access token.')
+            return
+        except alexa_errors.NoTokenAvailable:
+            connection.send_error(
+                msg['id'], 'alexa_relink',
+                'Please go to the Alexa app and re-link the Home Assistant '
+                'skill and then try to enable state reporting.'
+            )
+            return
+
     await cloud.client.prefs.async_update(**changes)
 
     connection.send_message(websocket_api.result_message(msg['id']))
@@ -575,7 +596,15 @@ async def alexa_sync(hass, connection, msg):
     cloud = hass.data[DOMAIN]
 
     with async_timeout.timeout(10):
-        success = await cloud.client.alexa_config.async_sync_entities()
+        try:
+            success = await cloud.client.alexa_config.async_sync_entities()
+        except alexa_errors.NoTokenAvailable:
+            connection.send_error(
+                msg['id'], 'alexa_relink',
+                'Please go to the Alexa app and re-link the Home Assistant '
+                'skill.'
+            )
+            return
 
     if success:
         connection.send_result(msg['id'])
diff --git a/homeassistant/components/websocket_api/connection.py b/homeassistant/components/websocket_api/connection.py
index 1aa1efc0eca..b8cce030109 100644
--- a/homeassistant/components/websocket_api/connection.py
+++ b/homeassistant/components/websocket_api/connection.py
@@ -1,4 +1,5 @@
 """Connection session."""
+import asyncio
 import voluptuous as vol
 
 from homeassistant.core import callback, Context
@@ -101,6 +102,9 @@ class ActiveConnection:
         elif isinstance(err, vol.Invalid):
             code = const.ERR_INVALID_FORMAT
             err_message = vol.humanize.humanize_error(msg, err)
+        elif isinstance(err, asyncio.TimeoutError):
+            code = const.ERR_TIMEOUT
+            err_message = 'Timeout'
         else:
             code = const.ERR_UNKNOWN_ERROR
             err_message = 'Unknown error'
diff --git a/homeassistant/components/websocket_api/const.py b/homeassistant/components/websocket_api/const.py
index 9c776e3b949..2f79ced7d99 100644
--- a/homeassistant/components/websocket_api/const.py
+++ b/homeassistant/components/websocket_api/const.py
@@ -16,6 +16,7 @@ ERR_HOME_ASSISTANT_ERROR = 'home_assistant_error'
 ERR_UNKNOWN_COMMAND = 'unknown_command'
 ERR_UNKNOWN_ERROR = 'unknown_error'
 ERR_UNAUTHORIZED = 'unauthorized'
+ERR_TIMEOUT = 'timeout'
 
 TYPE_RESULT = 'result'
 
diff --git a/tests/components/cloud/test_http_api.py b/tests/components/cloud/test_http_api.py
index 55cd9e9e2e5..bc60568f0d4 100644
--- a/tests/components/cloud/test_http_api.py
+++ b/tests/components/cloud/test_http_api.py
@@ -16,6 +16,7 @@ from homeassistant.components.cloud.const import (
 from homeassistant.components.google_assistant.helpers import (
     GoogleEntity)
 from homeassistant.components.alexa.entities import LightCapabilities
+from homeassistant.components.alexa import errors as alexa_errors
 
 from tests.common import mock_coro
 from tests.components.google_assistant import MockConfig
@@ -847,3 +848,53 @@ async def test_update_alexa_entity(
     assert prefs.alexa_entity_configs['light.kitchen'] == {
         'should_expose': False,
     }
+
+
+async def test_sync_alexa_entities_timeout(
+        hass, hass_ws_client, setup_api, mock_cloud_login):
+    """Test that timeout syncing Alexa entities."""
+    client = await hass_ws_client(hass)
+    with patch('homeassistant.components.cloud.alexa_config.AlexaConfig'
+               '.async_sync_entities', side_effect=asyncio.TimeoutError):
+        await client.send_json({
+            'id': 5,
+            'type': 'cloud/alexa/sync',
+        })
+        response = await client.receive_json()
+
+    assert not response['success']
+    assert response['error']['code'] == 'timeout'
+
+
+async def test_sync_alexa_entities_no_token(
+        hass, hass_ws_client, setup_api, mock_cloud_login):
+    """Test sync Alexa entities when we have no token."""
+    client = await hass_ws_client(hass)
+    with patch('homeassistant.components.cloud.alexa_config.AlexaConfig'
+               '.async_sync_entities',
+               side_effect=alexa_errors.NoTokenAvailable):
+        await client.send_json({
+            'id': 5,
+            'type': 'cloud/alexa/sync',
+        })
+        response = await client.receive_json()
+
+    assert not response['success']
+    assert response['error']['code'] == 'alexa_relink'
+
+
+async def test_enable_alexa_state_report_fail(
+        hass, hass_ws_client, setup_api, mock_cloud_login):
+    """Test enable Alexa entities state reporting when no token available."""
+    client = await hass_ws_client(hass)
+    with patch('homeassistant.components.cloud.alexa_config.AlexaConfig'
+               '.async_sync_entities',
+               side_effect=alexa_errors.NoTokenAvailable):
+        await client.send_json({
+            'id': 5,
+            'type': 'cloud/alexa/sync',
+        })
+        response = await client.receive_json()
+
+    assert not response['success']
+    assert response['error']['code'] == 'alexa_relink'