diff --git a/maubot/__main__.py b/maubot/__main__.py
index 5d5daec..9f8cafe 100644
--- a/maubot/__main__.py
+++ b/maubot/__main__.py
@@ -58,7 +58,7 @@ loop = asyncio.get_event_loop()
 
 init_db(db_session)
 clients = init_client(loop)
-init_plugin_instance_class(db_session, config)
+init_plugin_instance_class(db_session, config, loop)
 management_api = init_management(config, loop)
 server = MaubotServer(config, management_api, loop)
 
diff --git a/maubot/instance.py b/maubot/instance.py
index 924bf5a..51c9dcd 100644
--- a/maubot/instance.py
+++ b/maubot/instance.py
@@ -129,7 +129,10 @@ class PluginInstance:
             return
         self.log.debug("Stopping plugin instance...")
         self.running = False
-        await self.plugin.stop()
+        try:
+            await self.plugin.stop()
+        except Exception:
+            self.log.exception("Failed to stop instance")
         self.plugin = None
 
     @classmethod
diff --git a/maubot/loader/zip.py b/maubot/loader/zip.py
index c811848..a4f1d6e 100644
--- a/maubot/loader/zip.py
+++ b/maubot/loader/zip.py
@@ -151,7 +151,7 @@ class ZippedPluginLoader(PluginLoader):
 
     def _get_importer(self, reset_cache: bool = False) -> zipimporter:
         try:
-            if not self._importer:
+            if not self._importer or self._importer.archive != self.path:
                 self._importer = zipimporter(self.path)
             if reset_cache:
                 self._importer.reset_cache()
diff --git a/maubot/management/api/plugin.py b/maubot/management/api/plugin.py
index d07030c..03fb609 100644
--- a/maubot/management/api/plugin.py
+++ b/maubot/management/api/plugin.py
@@ -15,8 +15,10 @@
 # along with this program.  If not, see <https://www.gnu.org/licenses/>.
 from aiohttp import web
 from io import BytesIO
+from time import time
 import traceback
 import os.path
+import re
 
 from ...loader import PluginLoader, ZippedPluginLoader, MaubotZipImportError
 from .responses import (ErrPluginNotFound, ErrPluginInUse, plugin_import_error,
@@ -81,11 +83,14 @@ async def upload_new_plugin(content: bytes, pid: str, version: str) -> web.Respo
 async def upload_replacement_plugin(plugin: ZippedPluginLoader, content: bytes, new_version: str
                                     ) -> web.Response:
     dirname = os.path.dirname(plugin.path)
-    filename = os.path.basename(plugin.path)
-    if plugin.version in filename:
-        filename = filename.replace(plugin.version, new_version)
+    old_filename = os.path.basename(plugin.path)
+    if plugin.version in old_filename:
+        filename = old_filename.replace(plugin.version, new_version)
+        if filename == old_filename:
+            filename = re.sub(f"{re.escape(plugin.version)}(-ts[0-9]+)?",
+                              f"{new_version}-ts{int(time())}", old_filename)
     else:
-        filename = filename.rstrip(".mbp")
+        filename = old_filename.rstrip(".mbp")
         filename = f"{filename}-v{new_version}.mbp"
     path = os.path.join(dirname, filename)
     with open(path, "wb") as p: