diff --git a/hass_nabucasa/__init__.py b/hass_nabucasa/__init__.py
index d209889b9..fb1c32940 100644
--- a/hass_nabucasa/__init__.py
+++ b/hass_nabucasa/__init__.py
@@ -199,7 +199,7 @@ def write_user_info(self) -> None:
         if not base_path.exists():
             base_path.mkdir()
 
-        with atomic_write(str(self.user_info_path), overwrite=True) as fp:
+        with atomic_write(self.user_info_path, overwrite=True) as fp:
             fp.write(
                 json.dumps(
                     {
@@ -210,6 +210,7 @@ def write_user_info(self) -> None:
                     indent=4,
                 )
             )
+        self.user_info_path.chmod(0o600)
 
     async def start(self):
         """Start the cloud component."""
diff --git a/hass_nabucasa/acme.py b/hass_nabucasa/acme.py
index 74f47c9be..3795898f0 100644
--- a/hass_nabucasa/acme.py
+++ b/hass_nabucasa/acme.py
@@ -9,6 +9,7 @@
 import OpenSSL
 from acme import challenges, client, crypto_util, errors, messages
 import async_timeout
+from atomicwrites import atomic_write
 import attr
 from cryptography import x509
 from cryptography.hazmat.backends import default_backend
@@ -280,7 +281,8 @@ def _finish_challenge(self, handler: ChallengeHandler) -> None:
         else:
             _LOGGER.info("Create new certificate: %s", self.path_fullchain)
 
-        self.path_fullchain.write_text(order.fullchain_pem)
+        with atomic_write(self.path_fullchain, overwrite=True) as fp:
+            fp.write(order.fullchain_pem)
         self.path_fullchain.chmod(0o600)
 
     async def load_certificate(self) -> None:
@@ -368,9 +370,13 @@ async def issue_certificate(self) -> None:
             await self.cloud.run_executor(self._finish_challenge, challenge)
             await self.load_certificate()
         finally:
-            await cloud_api.async_remote_challenge_cleanup(
-                self.cloud, challenge.validation
-            )
+            try:
+                async with async_timeout.timeout(30):
+                    await cloud_api.async_remote_challenge_cleanup(
+                        self.cloud, challenge.validation
+                    )
+            except asyncio.TimeoutError:
+                _LOGGER.error("Failed to clean up challenge from NabuCasa DNS!")
 
     async def reset_acme(self) -> None:
         """Revoke and deactivate acme certificate/account."""
diff --git a/hass_nabucasa/remote.py b/hass_nabucasa/remote.py
index 33bcbc108..e94e51722 100644
--- a/hass_nabucasa/remote.py
+++ b/hass_nabucasa/remote.py
@@ -175,11 +175,14 @@ async def _finish_load_backend(self) -> None:
 
         await self._acme.hardening_files()
 
+        _LOGGER.debug("Waiting for aiohttp runner to come available")
+
         # aiohttp_runner comes available when Home Assistant has started.
         while self.cloud.client.aiohttp_runner is None:
             await asyncio.sleep(1)
 
         # Setup snitun / aiohttp wrapper
+        _LOGGER.debug("Initializing remote backend")
         context = await self._create_context()
         self._snitun = SniTunClientAioHttp(
             self.cloud.client.aiohttp_runner,
@@ -188,9 +191,13 @@ async def _finish_load_backend(self) -> None:
             snitun_port=443,
         )
 
+        _LOGGER.debug("Starting remote backend")
         await self._snitun.start()
         self.cloud.client.dispatcher_message(const.DISPATCH_REMOTE_BACKEND_UP)
 
+        _LOGGER.debug(
+            "Connecting remote backend: %s", self.cloud.client.remote_autostart
+        )
         # Connect to remote is autostart enabled
         if self.cloud.client.remote_autostart:
             self.cloud.run_task(self.connect())
diff --git a/tests/test_init.py b/tests/test_init.py
index 01078a6d4..3e3dcb28b 100644
--- a/tests/test_init.py
+++ b/tests/test_init.py
@@ -176,7 +176,7 @@ def test_write_user_info(cloud_client):
     cl.access_token = "test-access-token"
     cl.refresh_token = "test-refresh-token"
 
-    with patch("hass_nabucasa.atomic_write",) as mock_write:
+    with patch("pathlib.Path.chmod"), patch("hass_nabucasa.atomic_write") as mock_write:
         cl.write_user_info()
 
     mock_file = mock_write.return_value.__enter__.return_value