diff --git a/maubot/loader/zip.py b/maubot/loader/zip.py
index 323b58a..70cee5a 100644
--- a/maubot/loader/zip.py
+++ b/maubot/loader/zip.py
@@ -271,10 +271,20 @@ class ZippedPluginLoader(PluginLoader):
     @classmethod
     def trash(cls, file_path: str, new_name: str | None = None, reason: str = "error") -> None:
         if cls.trash_path == "delete":
-            os.remove(file_path)
+            try:
+                os.remove(file_path)
+            except FileNotFoundError:
+                pass
         else:
             new_name = new_name or f"{int(time())}-{reason}-{os.path.basename(file_path)}"
-            os.rename(file_path, os.path.abspath(os.path.join(cls.trash_path, new_name)))
+            try:
+                os.rename(file_path, os.path.abspath(os.path.join(cls.trash_path, new_name)))
+            except OSError as e:
+                cls.log.warning(f"Failed to rename {file_path}: {e} - trying to delete")
+                try:
+                    os.remove(file_path)
+                except FileNotFoundError:
+                    pass
 
     @classmethod
     def load_all(cls):
diff --git a/maubot/management/api/plugin_upload.py b/maubot/management/api/plugin_upload.py
index a1f0dfb..ea4fd1f 100644
--- a/maubot/management/api/plugin_upload.py
+++ b/maubot/management/api/plugin_upload.py
@@ -90,7 +90,7 @@ async def upload_replacement_plugin(
         replacement = (
             str(new_version)
             if plugin.meta.version != new_version
-            else f"{new_version}-ts{int(time())}"
+            else f"{new_version}-ts{int(time() * 1000)}"
         )
         filename = re.sub(
             f"{re.escape(str(plugin.meta.version))}(-ts[0-9]+)?", replacement, old_filename