diff --git a/test/parallel/test-debugger-extract-function-name.mjs b/test/parallel/test-debugger-extract-function-name.mjs
index a7de32ad4e2cf5..17c73c50c9ceae 100644
--- a/test/parallel/test-debugger-extract-function-name.mjs
+++ b/test/parallel/test-debugger-extract-function-name.mjs
@@ -10,23 +10,46 @@ import assert from 'assert';
 const cli = startCLI([fixtures.path('debugger', 'three-lines.js')]);
 
 try {
-  await cli.waitForInitialBreak();
+  await cli.waitFor(/Debugger attached\./);
+  await cli.waitForPrompt();
+  cli.writeLine('exec a = function func() {}; a;', true);
+  await cli.waitFor(/\[Function: func\]/);
   await cli.waitForPrompt();
-  await cli.command('exec a = function func() {}; a;');
   assert.match(cli.output, /\[Function: func\]/);
-  await cli.command('exec a = function func () {}; a;');
+
+  cli.writeLine('exec a = function func () {}; a;', true);
+  await cli.waitFor(/\[Function\]/);
+  await cli.waitForPrompt();
   assert.match(cli.output, /\[Function\]/);
-  await cli.command('exec a = function() {}; a;');
+
+  cli.writeLine('exec a = function() {}; a;', true);
+  await cli.waitFor(/\[Function: function\]/);
+  await cli.waitForPrompt();
   assert.match(cli.output, /\[Function: function\]/);
-  await cli.command('exec a = () => {}; a;');
+
+  cli.writeLine('exec a = () => {}; a;', true);
+  await cli.waitFor(/\[Function\]/);
+  await cli.waitForPrompt();
   assert.match(cli.output, /\[Function\]/);
-  await cli.command('exec a = function* func() {}; a;');
+
+  cli.writeLine('exec a = function* func() {}; a;', true);
+  await cli.waitFor(/\[GeneratorFunction: func\]/);
+  await cli.waitForPrompt();
   assert.match(cli.output, /\[GeneratorFunction: func\]/);
-  await cli.command('exec a = function *func() {}; a;');
+
+  cli.writeLine('exec a = function *func() {}; a;', true);
+  await cli.waitFor(/\[GeneratorFunction: \*func\]/);
+  await cli.waitForPrompt();
   assert.match(cli.output, /\[GeneratorFunction: \*func\]/);
-  await cli.command('exec a = function*func() {}; a;');
+
+  cli.writeLine('exec a = function*func() {}; a;', true);
+  await cli.waitFor(/\[GeneratorFunction: function\*func\]/);
+  await cli.waitForPrompt();
   assert.match(cli.output, /\[GeneratorFunction: function\*func\]/);
-  await cli.command('exec a = function * func() {}; a;');
+
+  cli.writeLine('exec a = function * func() {}; a;', true);
+  await cli.waitFor(/\[GeneratorFunction\]/);
+  await cli.waitForPrompt();
   assert.match(cli.output, /\[GeneratorFunction\]/);
 } finally {
   cli.quit();
diff --git a/test/parallel/test-debugger-random-port-with-inspect-port.js b/test/parallel/test-debugger-random-port-with-inspect-port.js
index a7e74c0dbae6d6..9256b3cd1d02ca 100644
--- a/test/parallel/test-debugger-random-port-with-inspect-port.js
+++ b/test/parallel/test-debugger-random-port-with-inspect-port.js
@@ -13,7 +13,7 @@ const script = fixtures.path('debugger', 'three-lines.js');
 const cli = startCLI(['--inspect-port=0', script], [], {}, { randomPort: false });
 
 (async () => {
-  await cli.waitForInitialBreak();
+  await cli.waitFor(/Debugger attached\./);
   await cli.waitForPrompt();
   assert.match(cli.output, /debug>/, 'prints a prompt');
   assert.match(
diff --git a/test/parallel/test-debugger-watch-validation.js b/test/parallel/test-debugger-watch-validation.js
index 46307c18d55526..0e92d19a748b95 100644
--- a/test/parallel/test-debugger-watch-validation.js
+++ b/test/parallel/test-debugger-watch-validation.js
@@ -11,7 +11,8 @@ const assert = require('assert');
 const cli = startCLI([fixtures.path('debugger/break.js')]);
 
 (async () => {
-  await cli.waitForInitialBreak();
+  await cli.waitFor(/Debugger attached\./);
+  await cli.waitForPrompt();
   await cli.command('watch()');
   await cli.waitFor(/ERR_INVALID_ARG_TYPE/);
   assert.match(cli.output, /TypeError \[ERR_INVALID_ARG_TYPE\]: The "expression" argument must be of type string\. Received undefined/);