diff --git a/repertory/librepertory/src/drives/winfsp/winfsp_drive.cpp b/repertory/librepertory/src/drives/winfsp/winfsp_drive.cpp
index 0f31c3db..9b333b70 100644
--- a/repertory/librepertory/src/drives/winfsp/winfsp_drive.cpp
+++ b/repertory/librepertory/src/drives/winfsp/winfsp_drive.cpp
@@ -40,6 +40,7 @@
 #include "utils/polling.hpp"
 #include "utils/string.hpp"
 #include "utils/time.hpp"
+#include "utils/timeout.hpp"
 #include "utils/utils.hpp"
 
 namespace repertory {
@@ -133,7 +134,9 @@ auto winfsp_drive::winfsp_service::OnStart(ULONG /*Argc*/, PWSTR * /*Argv*/)
 auto winfsp_drive::winfsp_service::OnStop() -> NTSTATUS {
   REPERTORY_USES_FUNCTION_NAME();
 
+  timeout stop_timeout([]() { app_config::set_stop_requested(); }, 30s);
   host_.Unmount();
+  stop_timeout.disable();
 
   if (not lock_.set_mount_state(false, "", -1)) {
     utils::error::raise_error(function_name, "failed to set mount state");
diff --git a/repertory/librepertory/src/file_manager/cache_size_mgr.cpp b/repertory/librepertory/src/file_manager/cache_size_mgr.cpp
index 974004a0..ce7d1e09 100644
--- a/repertory/librepertory/src/file_manager/cache_size_mgr.cpp
+++ b/repertory/librepertory/src/file_manager/cache_size_mgr.cpp
@@ -70,7 +70,7 @@ auto cache_size_mgr::expand(std::uint64_t size) -> api_error {
                                                              max_cache_size);
       last_cache_size = cache_size_;
     }
-    notify_.wait(lock, 5s);
+    notify_.wait_for(lock, 5s);
   }
 
   notify_.notify_all();