diff --git a/Vagrantfile b/Vagrantfile
index 9d2cff802..ec9442d24 100644
--- a/Vagrantfile
+++ b/Vagrantfile
@@ -47,10 +47,12 @@ $ sudo /vagrant/run --develop
 Plinth will be available at https://localhost:4430/plinth (with
 an invalid SSL certificate).
 "
+
   config.trigger.before :destroy do |trigger|
-    trigger.warn = "Dropping Plinth database"
-    trigger.run_remote = {
-      inline: "rm /vagrant/data/var/lib/plinth/plinth.sqlite3"
+    trigger.warn = "Performing cleanup steps"
+    trigger.run = {
+      path: "post-box-destroy.py"
     }
   end
+  config.vm.boot_timeout=1200
 end
diff --git a/post-box-destroy.py b/post-box-destroy.py
new file mode 100755
index 000000000..90bba379a
--- /dev/null
+++ b/post-box-destroy.py
@@ -0,0 +1,37 @@
+#!/usr/bin/python3
+# -*- mode: python -*-
+#
+# This file is part of FreedomBox.
+#
+# This program is free software: you can redistribute it and/or modify
+# it under the terms of the GNU Affero General Public License as
+# published by the Free Software Foundation, either version 3 of the
+# License, or (at your option) any later version.
+#
+# This program is distributed in the hope that it will be useful,
+# but WITHOUT ANY WARRANTY; without even the implied warranty of
+# MERCHANTABILITY or FITNESS FOR A PARTICULAR PURPOSE.  See the
+# GNU Affero General Public License for more details.
+#
+# You should have received a copy of the GNU Affero General Public License
+# along with this program.  If not, see <http://www.gnu.org/licenses/>.
+#
+"""
+Cleanup actions to be run when a vagrant box is destroyed.
+"""
+
+import os
+
+# Drop Plinth database
+try:
+    os.remove('data/var/lib/plinth/plinth.sqlite3')
+except OSError:
+    pass
+
+# Truncate status.log
+with open('data/var/log/plinth/status.log', 'w') as status_log:
+    status_log.truncate()
+
+# Truncate access.log
+with open('data/var/log/plinth/access.log', 'w') as access_log:
+    access_log.truncate()