diff --git a/pydatalab/pydatalab/remote_filesystems.py b/pydatalab/pydatalab/remote_filesystems.py
index 380817ce7..e7f62078a 100644
--- a/pydatalab/pydatalab/remote_filesystems.py
+++ b/pydatalab/pydatalab/remote_filesystems.py
@@ -208,12 +208,43 @@ def _call_remote_tree(
         except Exception as exc:
             raise RuntimeError(f"Remote tree process {command!r} returned: {exc!r}")
         if stderr:
-            raise RuntimeError(f"Remote tree process {command!r} returned: {stderr!r}")
+            # Do not return the bare stderr, but instead specialise the error message to common errors
+            if "WARNING: REMOTE HOST IDENTIFICATION HAS CHANGED!" in stderr.decode("utf-8"):
+                msg = f"Remote host identification has changed for {hostname}: please contact the administrator of this datalab deployment."
+                LOGGER.error(
+                    "Remote host identification for %s has changed, failed to update remote directories",
+                    hostname,
+                )
+            else:
+                msg = "Remote tree process returned an error: please contact the administrator of this datalab deployment."
+                LOGGER.error(
+                    "Remote tree process on %s returned an error: %s",
+                    hostname,
+                    stderr.decode("utf-8"),
+                )
+            raise RuntimeError(msg)
 
         try:
             return json.loads(stdout)
         except Exception:
-            raise RuntimeError(f"Remote tree process {command!r} returned: {stdout!r}")
+            if "error opening dir" in stdout.decode("utf-8"):
+                msg = "Can no longer access the configured directory on the remote system; please contact the administrator of this datalab deployment."
+                LOGGER.error(
+                    "Remote directory %s on %s no longer accessible. Response: %s",
+                    directory_path,
+                    hostname,
+                    stdout.decode("utf-8"),
+                )
+            else:
+                msg = "Remote tree process failed with an unhandled error; please contact the administrator of this datalab deployment."
+                LOGGER.error(
+                    "Remote directory syncing for  %s on %s failed. Response: %s",
+                    directory_path,
+                    hostname,
+                    stdout.decode("utf-8"),
+                )
+
+            raise RuntimeError(msg)
 
     if hostname:
         LOGGER.debug(f"Calling remote {tree_command} on {directory_path}")
diff --git a/pydatalab/tasks.py b/pydatalab/tasks.py
index ab7cacadc..7e48121af 100644
--- a/pydatalab/tasks.py
+++ b/pydatalab/tasks.py
@@ -290,7 +290,7 @@ def check_item_validity(_, base_url: str | None = None, starting_materials: bool
 
 
 @task
-def check_remotes(_, base_url: str | None = None):
+def check_remotes(_, base_url: str | None = None, invalidate_cache: bool = False):
     """This task looks up all configured remotes and checks that they
     can be synced.
 
@@ -299,6 +299,7 @@ def check_remotes(_, base_url: str | None = None):
 
     Parameters:
         base_url: The API URL.
+        invalidate_cache: Whether to force cache invalidation.
 
     """
 
@@ -320,7 +321,10 @@ def check_remotes(_, base_url: str | None = None):
     if not user_response.status_code == 200:
         raise SystemExit(f"Could not get current user: {user_response.content!r}")
 
-    directory_response = requests.get(f"{base_url}/list-remote-directories/", headers=headers)
+    directory_response = requests.get(
+        f"{base_url}/list-remote-directories?invalidate_cache={'1' if invalidate_cache else '0'}",
+        headers=headers,
+    )
 
     if directory_response.status_code != 200:
         raise SystemExit(f"Could not get remote directories: {directory_response}")
@@ -331,7 +335,9 @@ def check_remotes(_, base_url: str | None = None):
     for d in directory_structures:
         if d["status"] == "error":
             log.error(f"ꙮ {d['name']!r}: {d['contents'][0]['details']!r}")
-        elif d["type"] == "toplevel":
+        elif d["status"] == "cached":
+            log.info(f"✩ {d['name']!r}: {d['last_updated']!r}")
+        elif d["status"] == "updated":
             log.info(f"✓ {d['name']!r}: {d['last_updated']!r}")