diff --git a/moonraker/components/file_manager/file_manager.py b/moonraker/components/file_manager/file_manager.py
index 731547d..e93dec7 100644
--- a/moonraker/components/file_manager/file_manager.py
+++ b/moonraker/components/file_manager/file_manager.py
@@ -268,15 +268,29 @@ class FileManager:
                 f"Supplied path ({path}) for ({root}) is invalid. Make sure\n"
                 "that the path exists and is not the file system root.")
             return False
-        permissions = os.R_OK
+        # Check Folder Permissions
+        missing_perms = []
+        try:
+            # Test read
+            os.listdir(path)
+        except PermissionError:
+            missing_perms.append("READ")
+        except Exception:
+            logging.exception(f"Error testing read access for root {root}")
         if full_access:
-            permissions |= os.W_OK
+            if (
+                os.access in os.supports_effective_ids and
+                not os.access(path, os.W_OK, effective_ids=True)
+            ):
+                missing_perms.append("WRITE")
             self.full_access_roots.add(root)
-        if not os.access(path, permissions):
-            self.server.add_warning(
-                f"Moonraker does not have permission to access path "
-                f"({path}) for ({root}).")
-            return False
+        if missing_perms:
+            mpstr = " | ".join(missing_perms)
+            self.server.add_log_rollover_item(
+                f"fm_reg_perms_{root}",
+                f"file_manager: Moonraker has detected the following missing "
+                f"permissions for root folder '{root}': {mpstr}"
+            )
         if path != self.file_paths.get(root, ""):
             self.file_paths[root] = path
             self.server.register_static_file_handler(root, path)
@@ -834,8 +848,14 @@ class FileManager:
         if unzip_ufp:
             filename = os.path.splitext(filename)[0] + ".gcode"
             dest_path = os.path.splitext(dest_path)[0] + ".gcode"
-        if os.path.isfile(dest_path) and not os.access(dest_path, os.W_OK):
-            raise self.server.error(f"File is read-only: {dest_path}")
+        if (
+            os.path.isfile(dest_path) and
+            os.access in os.supports_effective_ids and
+            not os.access(dest_path, os.W_OK, effective_ids=True)
+        ):
+            logging.info(
+                f"Destination file exists and appears to be read-only: {dest_path}"
+            )
         return {
             'root': root,
             'filename': filename,
@@ -1811,17 +1831,41 @@ class InotifyObserver(BaseFileSystemObserver):
         try:
             root_node = InotifyRootNode(self, root, root_path)
         except Exception:
+            logging.exception(f"Inotify: failed to create root node '{root}'")
+            self.server.add_warning(
+                f"file_manager: Failed to create inotify root node {root}. "
+                "See moonraker.log for details.",
+                log=False
+            )
             return
         self.watched_roots[root] = root_node
         if self.initialized:
-            mevts = root_node.scan_node()
+            try:
+                mevts = root_node.scan_node()
+            except Exception:
+                logging.exception(f"Inotify: failed to scan root '{root}'")
+                self.server.add_warning(
+                    f"file_manager: Failed to scan inotify root node '{root}'. "
+                    "See moonraker.log for details.",
+                    log=False
+                )
+                return
             self.log_nodes()
             self.event_loop.register_callback(
                 self._notify_root_updated, mevts, root, root_path)
 
     def initialize(self) -> None:
         for root, node in self.watched_roots.items():
-            evts = node.scan_node()
+            try:
+                evts = node.scan_node()
+            except Exception:
+                logging.exception(f"Inotify: failed to scan root '{root}'")
+                self.server.add_warning(
+                    f"file_manager: Failed to scan inotify root node '{root}'. "
+                    "See moonraker.log for details.",
+                    log=False
+                )
+                continue
             if not evts:
                 continue
             root_path = node.get_path()