diff --git a/test/support/console_test_case.rb b/test/support/console_test_case.rb
index 081b3f335..976a9f908 100644
--- a/test/support/console_test_case.rb
+++ b/test/support/console_test_case.rb
@@ -195,12 +195,20 @@ def run_test_scenario cmd, test_info
         # result of `gets` return this exception in some platform
         rescue Timeout::Error
           assert_block(create_message("TIMEOUT ERROR (#{TIMEOUT_SEC} sec)", test_info)) { false }
+        rescue Test::Unit::AssertionFailedError
+          is_fail = true
+          raise
         ensure
-          kill_remote_debuggee test_info
+          kill_remote_debuggee(test_info, failed: is_fail == true)
           # kill debug console process
           read.close
           write.close
-          kill_safely pid, :debugger, test_info
+          if is_fail == true
+            kill_safely pid, :debugger, test_info, sec: 0
+          end
+          if name = test_info.failed_process && !is_fail
+            flunk(create_message("Expected the #{name} program to finish", test_info))
+          end
         end
       end
     end
diff --git a/test/support/test_case.rb b/test/support/test_case.rb
index 976ad30fc..ea89c069e 100644
--- a/test/support/test_case.rb
+++ b/test/support/test_case.rb
@@ -122,8 +122,8 @@ def wait_pid pid, sec
       true
     end
 
-    def kill_safely pid, name, test_info
-      return if wait_pid pid, TIMEOUT_SEC
+    def kill_safely pid, name, test_info, sec: TIMEOUT_SEC
+      return if wait_pid pid, sec
 
       test_info.failed_process = name
 
@@ -141,10 +141,14 @@ def check_error(error, test_info)
       end
     end
 
-    def kill_remote_debuggee test_info
+    def kill_remote_debuggee test_info, failed: false
       return unless r = test_info.remote_info
 
-      kill_safely r.pid, :remote, test_info
+      if failed
+        kill_safely r.pid, :remote, test_info, sec: 2
+      else
+        kill_safely r.pid, :remote, test_info
+      end
       r.reader_thread.kill
       # Because the debuggee may be terminated by executing the following operations, we need to run them after `kill_safely` method.
       r.r.close