diff --git a/lldb/source/Host/windows/MainLoopWindows.cpp b/lldb/source/Host/windows/MainLoopWindows.cpp
index 0a5a35e9db9dd..f3ab2a710cd01 100644
--- a/lldb/source/Host/windows/MainLoopWindows.cpp
+++ b/lldb/source/Host/windows/MainLoopWindows.cpp
@@ -28,7 +28,7 @@ static DWORD ToTimeout(std::optional<MainLoopWindows::TimePoint> point) {
     return WSA_INFINITE;
 
   nanoseconds dur = (std::max)(*point - steady_clock::now(), nanoseconds(0));
-  return duration_cast<milliseconds>(dur).count();
+  return ceil<milliseconds>(dur).count();
 }
 
 MainLoopWindows::MainLoopWindows() {