diff --git a/src/bin/pg_ctl/pg_ctl.c b/src/bin/pg_ctl/pg_ctl.c
index e7e878c22f..cab6eb9472 100644
--- a/src/bin/pg_ctl/pg_ctl.c
+++ b/src/bin/pg_ctl/pg_ctl.c
@@ -1167,12 +1174,17 @@ do_reload(void)
 		exit(1);
 	}
 
-	if (kill(pid, sig) != 0)
+for (int i = 1; i <= 100; i++)
+{
+int res, en;
+	if ((res = kill(pid, sig)) != 0)
 	{
-		write_stderr(_("%s: could not send reload signal (PID: %d): %m\n"),
-					 progname, (int) pid);
+en = errno;
+		write_stderr(_("%s: could not send reload signal (PID: %d), iteration: %d, res: %d, errno: %d: %m\n"),
+					 progname, (int) pid, i, res, en);
 		exit(1);
 	}
+}
 
 	print_msg(_("server signaled\n"));
 }
diff --git a/src/port/kill.c b/src/port/kill.c
index 412c2f19c1..b3d2c00796 100644
--- a/src/port/kill.c
+++ b/src/port/kill.c
@@ -70,6 +70,7 @@ pgkill(int pid, int sig)
 		return 0;
 	}
 
+int le = GetLastError();
 	switch (GetLastError())
 	{
 		case ERROR_BROKEN_PIPE:
@@ -89,6 +90,7 @@ pgkill(int pid, int sig)
 			errno = EPERM;
 			return -1;
 		default:
+fprintf(stderr, "!!!pgkill| GetLastError(): %d\n", le);
 			errno = EINVAL;		/* unexpected */
 			return -1;
 	}