diff --git a/environment/docker/power.go b/environment/docker/power.go
index d08076d..6187d83 100644
--- a/environment/docker/power.go
+++ b/environment/docker/power.go
@@ -102,19 +102,6 @@ func (e *Environment) Start() error {
 		return errors.WithStack(err)
 	}
 
-	// Update the configuration files defined for the server before beginning the boot process.
-	// This process executes a bunch of parallel updates, so we just block until that process
-	// is completee. Any errors as a result of this will just be bubbled out in the logger,
-	// we don't need to actively do anything about it at this point, worst comes to worst the
-	// server starts in a weird state and the user can manually adjust.
-	// e.Server.UpdateConfigurationFiles()
-	//
-	// // Reset the permissions on files for the server before actually trying
-	// // to start it.
-	// if err := e.Server.Filesystem.Chown("/"); err != nil {
-	// 	return errors.WithStack(err)
-	// }
-
 	ctx, cancel := context.WithTimeout(context.Background(), time.Second*10)
 	defer cancel()
 
diff --git a/server/power.go b/server/power.go
index 3ead824..ab868fb 100644
--- a/server/power.go
+++ b/server/power.go
@@ -143,7 +143,19 @@ func (s *Server) onBeforeStart() error {
 		return errors.New("cannot start server, not enough disk space available")
 	}
 
+	// Update the configuration files defined for the server before beginning the boot process.
+	// This process executes a bunch of parallel updates, so we just block until that process
+	// is completee. Any errors as a result of this will just be bubbled out in the logger,
+	// we don't need to actively do anything about it at this point, worst comes to worst the
+	// server starts in a weird state and the user can manually adjust.
+	s.PublishConsoleOutputFromDaemon("Updating process configuration files...")
 	s.UpdateConfigurationFiles()
 
+	s.PublishConsoleOutputFromDaemon("Ensuring file permissions are set correctly, this could take a few seconds...")
+	// Ensure all of the server file permissions are set correctly before booting the process.
+	if err := s.Filesystem.Chown("/"); err != nil {
+		return errors.WithMessage(err, "failed to chown root server directory during pre-boot process")
+	}
+
 	return nil
 }
\ No newline at end of file