diff --git a/src/wine-host/xdnd-proxy.cpp b/src/wine-host/xdnd-proxy.cpp
index 3c28dc34..58cf2c69 100644
--- a/src/wine-host/xdnd-proxy.cpp
+++ b/src/wine-host/xdnd-proxy.cpp
@@ -443,7 +443,7 @@ void WineXdndProxy::run_xdnd_loop() {
     while (!drop_finished) {
         // In case that window somehow becomes unresponsive or disappears, we
         // will set a timeout here to avoid hanging
-        if (std::chrono::steady_clock::now() - wait_start < 5s) {
+        if (std::chrono::steady_clock::now() - wait_start > 5s) {
             maybe_leave_last_window();
             break;
         }