diff --git a/src/crystal/system/win32/file_descriptor.cr b/src/crystal/system/win32/file_descriptor.cr
index 1f277505302a..4265701cd8b2 100644
--- a/src/crystal/system/win32/file_descriptor.cr
+++ b/src/crystal/system/win32/file_descriptor.cr
@@ -195,7 +195,11 @@ module Crystal::System::FileDescriptor
   end
 
   def file_descriptor_close(&)
-    if LibC.CloseHandle(windows_handle) == 0
+    # Clear the @volatile_fd before actually closing it in order to
+    # reduce the chance of reading an outdated handle value
+    handle = LibC::HANDLE.new(@volatile_fd.swap(LibC::INVALID_HANDLE_VALUE.address))
+
+    if LibC.CloseHandle(handle) == 0
       yield
     end
   end