On pollset shutdown, we need to unconditionally start the kick cascade.
diff --git a/src/core/iomgr/pollset_windows.c b/src/core/iomgr/pollset_windows.c
index d0507af..1f750f6 100644
--- a/src/core/iomgr/pollset_windows.c
+++ b/src/core/iomgr/pollset_windows.c
@@ -39,6 +39,7 @@
 
 #include "src/core/iomgr/alarm_internal.h"
 #include "src/core/iomgr/iomgr_internal.h"
+#include "src/core/iomgr/pollset.h"
 #include "src/core/iomgr/pollset_windows.h"
 
 /* There isn't really any such thing as a pollset under Windows, due to the
@@ -54,6 +55,7 @@
 void grpc_pollset_shutdown(grpc_pollset *pollset,
                            void (*shutdown_done)(void *arg),
                            void *shutdown_done_arg) {
+  grpc_pollset_kick(pollset);
   shutdown_done(shutdown_done_arg);
 }