diff --git a/test/support/assertions_test.rb b/test/support/assertions_test.rb
index d03ad5dfb..8cf08a820 100644
--- a/test/support/assertions_test.rb
+++ b/test/support/assertions_test.rb
@@ -12,7 +12,7 @@ def program
 
     def test_the_helper_takes_a_string_expectation_and_escape_it
       assert_raise_message(/Expected to include `"foobar\\\\?/) do
-        debug_code(program, remote: false) do
+        debug_code(program) do
           assert_line_text("foobar?")
         end
       end
@@ -49,6 +49,30 @@ def test_the_helper_raises_an_error_with_invalid_expectation
         end
       end
     end
+
+    def test_the_test_fails_when_debuggee_on_unix_domain_socket_mode_doesnt_exist_after_scenarios
+      assert_raise_message(/Expected to include `"foobar\\\\?/) do
+        prepare_test_environment(program, steps) do
+          debug_code_on_unix_domain_socket()
+        end
+      end
+    end
+
+    def test_the_test_fails_when_debuggee_on_tcpip_mode_doesnt_exist_after_scenarios
+      assert_raise_message(/Expected to include `"foobar\\\\?/) do
+        prepare_test_environment(program, steps) do
+          debug_code_on_tcpip()
+        end
+      end
+    end
+
+    private
+
+    def steps
+      Proc.new{
+        assert_line_text("foobar?")
+      }
+    end
   end
 end
 
diff --git a/test/support/console_test_case.rb b/test/support/console_test_case.rb
index 1f42fa438..bd5797c39 100644
--- a/test/support/console_test_case.rb
+++ b/test/support/console_test_case.rb
@@ -176,11 +176,23 @@ def run_test_scenario cmd, test_info
             check_error(/DEBUGGEE Exception/, test_info)
             assert_empty_queue test_info
           end
+
+          if r = test_info.remote_info
+            assert_program_finish test_info, r.pid, :debuggee
+          end
+
+          assert_program_finish test_info, pid, :debugger
         # result of `gets` return this exception in some platform
         # https://github.com/ruby/ruby/blob/master/ext/pty/pty.c#L729-L736
         rescue Errno::EIO => e
           check_error(/DEBUGGEE Exception/, test_info)
           assert_empty_queue test_info, exception: e
+          if r = test_info.remote_info
+            assert_program_finish test_info, r.pid, :debuggee
+          end
+
+          assert_program_finish test_info, pid, :debugger
+        # result of `gets` return this exception in some platform
         rescue Timeout::Error
           assert_block(create_message("TIMEOUT ERROR (#{TIMEOUT_SEC} sec)", test_info)) { false }
         ensure
@@ -189,13 +201,14 @@ def run_test_scenario cmd, test_info
           read.close
           write.close
           kill_safely pid, :debugger, test_info
-          if name = test_info.failed_process
-            assert_block(create_message("Expected the #{name} program to finish", test_info)) { false }
-          end
         end
       end
     end
 
+    def assert_program_finish test_info, pid, name
+      assert_block(create_message("Expected the #{name} program to finish", test_info)) { wait_pid pid, TIMEOUT_SEC }
+    end
+
     def prepare_test_environment(program, test_steps, &block)
       ENV['RUBY_DEBUG_NO_COLOR'] = 'true'
       ENV['RUBY_DEBUG_TEST_UI'] = 'terminal'
diff --git a/test/support/test_case.rb b/test/support/test_case.rb
index 08787586c..59e3bfaa0 100644
--- a/test/support/test_case.rb
+++ b/test/support/test_case.rb
@@ -118,6 +118,8 @@ def wait_pid pid, sec
       end
 
       false
+    rescue Errno::ECHILD
+      true
     end
 
     def kill_safely pid, name, test_info
diff --git a/test/support/test_case_test.rb b/test/support/test_case_test.rb
index 929c67d56..b87457ac0 100644
--- a/test/support/test_case_test.rb
+++ b/test/support/test_case_test.rb
@@ -61,7 +61,7 @@ def steps
     end
 
     def test_the_test_fails_when_debuggee_on_unix_domain_socket_mode_doesnt_exist_after_scenarios
-      assert_raise_message(/Expected the remote program to finish/) do
+      assert_raise_message(/Expected the debuggee program to finish/) do
         prepare_test_environment(program, steps) do
           debug_code_on_unix_domain_socket()
         end
@@ -69,7 +69,7 @@ def test_the_test_fails_when_debuggee_on_unix_domain_socket_mode_doesnt_exist_af
     end
 
     def test_the_test_fails_when_debuggee_on_tcpip_mode_doesnt_exist_after_scenarios
-      assert_raise_message(/Expected the remote program to finish/) do
+      assert_raise_message(/Expected the debuggee program to finish/) do
         prepare_test_environment(program, steps) do
           debug_code_on_tcpip()
         end