diff --git a/test/cli/backtrace.test.js b/test/cli/backtrace.test.js
index 9cd8a82..127ea56 100644
--- a/test/cli/backtrace.test.js
+++ b/test/cli/backtrace.test.js
@@ -14,7 +14,7 @@ test('display and navigate backtrace', (t) => {
     throw error;
   }
 
-  return cli.waitFor(/break/)
+  return cli.waitForInitialBreak()
     .then(() => cli.waitForPrompt())
     .then(() => cli.stepCommand('c'))
     .then(() => cli.command('bt'))
diff --git a/test/cli/break.test.js b/test/cli/break.test.js
index 1c662d6..5de3e52 100644
--- a/test/cli/break.test.js
+++ b/test/cli/break.test.js
@@ -14,12 +14,12 @@ test('stepping through breakpoints', (t) => {
     throw error;
   }
 
-  return cli.waitFor(/break/)
+  return cli.waitForInitialBreak()
     .then(() => cli.waitForPrompt())
     .then(() => {
       t.match(
         cli.output,
-        `break in ${script}:1`,
+        ` in ${script}:1`,
         'pauses in the first line of the script');
       t.match(
         cli.output,
@@ -30,7 +30,7 @@ test('stepping through breakpoints', (t) => {
     .then(() => {
       t.match(
         cli.output,
-        `break in ${script}:2`,
+        ` in ${script}:2`,
         'pauses in next line of the script');
       t.match(
         cli.output,
@@ -41,7 +41,7 @@ test('stepping through breakpoints', (t) => {
     .then(() => {
       t.match(
         cli.output,
-        `break in ${script}:3`,
+        ` in ${script}:3`,
         'pauses in next line of the script');
       t.match(
         cli.output,
@@ -52,7 +52,7 @@ test('stepping through breakpoints', (t) => {
     .then(() => {
       t.match(
         cli.output,
-        `break in ${script}:10`,
+        ` in ${script}:10`,
         'pauses on the next breakpoint');
       t.match(
         cli.output,
@@ -94,21 +94,21 @@ test('stepping through breakpoints', (t) => {
     .then(() => {
       t.match(
         cli.output,
-        'break in timers.js',
+        ' in timers.js',
         'entered timers.js');
     })
     .then(() => cli.stepCommand('cont'))
     .then(() => {
       t.match(
         cli.output,
-        `break in ${script}:16`,
+        ` in ${script}:16`,
         'found breakpoint we set above w/ line number only');
     })
     .then(() => cli.stepCommand('cont'))
     .then(() => {
       t.match(
         cli.output,
-        `break in ${script}:6`,
+        ` in ${script}:6`,
         'found breakpoint we set above w/ line number & script');
     })
     .then(() => cli.stepCommand(''))
@@ -132,7 +132,7 @@ test('sb before loading file', (t) => {
     throw error;
   }
 
-  return cli.waitFor(/break/)
+  return cli.waitForInitialBreak()
     .then(() => cli.waitForPrompt())
     .then(() => cli.command('sb("other.js", 3)'))
     .then(() => {
@@ -145,7 +145,7 @@ test('sb before loading file', (t) => {
     .then(() => {
       t.match(
         cli.output,
-        `break in ${otherScript}:3`,
+        ` in ${otherScript}:3`,
         'found breakpoint in file that was not loaded yet');
     })
     .then(() => cli.quit())
@@ -161,7 +161,7 @@ test('clearBreakpoint', (t) => {
     throw error;
   }
 
-  return cli.waitFor(/break/)
+  return cli.waitForInitialBreak()
     .then(() => cli.waitForPrompt())
     .then(() => cli.command('sb("break.js", 3)'))
     .then(() => cli.command('sb("break.js", 9)'))
@@ -187,7 +187,7 @@ test('clearBreakpoint', (t) => {
     .then(() => {
       t.match(
         cli.output,
-        `break in ${script}:9`,
+        ` in ${script}:9`,
         'hits the 2nd breakpoint because the 1st was cleared');
     })
     .then(() => cli.quit())
diff --git a/test/cli/exceptions.test.js b/test/cli/exceptions.test.js
index b66c09f..5a9f814 100644
--- a/test/cli/exceptions.test.js
+++ b/test/cli/exceptions.test.js
@@ -14,10 +14,10 @@ test('break on (uncaught) exceptions', (t) => {
     throw error;
   }
 
-  return cli.waitFor(/break/)
+  return cli.waitForInitialBreak()
     .then(() => cli.waitForPrompt())
     .then(() => {
-      t.match(cli.output, `break in ${script}:1`);
+      t.match(cli.output, ` in ${script}:1`);
     })
     // making sure it will die by default:
     .then(() => cli.command('c'))
@@ -26,7 +26,7 @@ test('break on (uncaught) exceptions', (t) => {
     // Next run: With `breakOnException` it pauses in both places
     .then(() => cli.stepCommand('r'))
     .then(() => {
-      t.match(cli.output, `break in ${script}:1`);
+      t.match(cli.output, ` in ${script}:1`);
     })
     .then(() => cli.command('breakOnException'))
     .then(() => cli.stepCommand('c'))
@@ -42,7 +42,7 @@ test('break on (uncaught) exceptions', (t) => {
     .then(() => cli.command('breakOnUncaught'))
     .then(() => cli.stepCommand('r')) // also, the setting survives the restart
     .then(() => {
-      t.match(cli.output, `break in ${script}:1`);
+      t.match(cli.output, ` in ${script}:1`);
     })
     .then(() => cli.stepCommand('c'))
     .then(() => {
@@ -53,7 +53,7 @@ test('break on (uncaught) exceptions', (t) => {
     .then(() => cli.command('breakOnNone'))
     .then(() => cli.stepCommand('r'))
     .then(() => {
-      t.match(cli.output, `break in ${script}:1`);
+      t.match(cli.output, ` in ${script}:1`);
     })
     .then(() => cli.command('c'))
     .then(() => cli.waitFor(/disconnect/))
diff --git a/test/cli/exec.test.js b/test/cli/exec.test.js
index 5c64713..acfd6e3 100644
--- a/test/cli/exec.test.js
+++ b/test/cli/exec.test.js
@@ -11,7 +11,7 @@ test('examples/alive.js', (t) => {
     throw error;
   }
 
-  return cli.waitFor(/break/)
+  return cli.waitForInitialBreak()
     .then(() => cli.waitForPrompt())
     .then(() => cli.command('exec [typeof heartbeat, typeof process.exit]'))
     .then(() => {
@@ -60,7 +60,7 @@ test('exec .scope', (t) => {
     throw error;
   }
 
-  return cli.waitFor(/break/)
+  return cli.waitForInitialBreak()
     .then(() => cli.waitForPrompt())
     .then(() => cli.stepCommand('c'))
     .then(() => cli.command('exec .scope'))
diff --git a/test/cli/help.test.js b/test/cli/help.test.js
index 11a9358..9f0c081 100644
--- a/test/cli/help.test.js
+++ b/test/cli/help.test.js
@@ -11,7 +11,7 @@ test('examples/empty.js', (t) => {
     throw error;
   }
 
-  return cli.waitFor(/break/)
+  return cli.waitForInitialBreak()
     .then(() => cli.waitForPrompt())
     .then(() => cli.command('help'))
     .then(() => {
diff --git a/test/cli/launch.test.js b/test/cli/launch.test.js
index 99c6ce0..0af27b1 100644
--- a/test/cli/launch.test.js
+++ b/test/cli/launch.test.js
@@ -9,7 +9,7 @@ test('examples/empty.js', (t) => {
   const script = Path.join('examples', 'empty.js');
   const cli = startCLI([script]);
 
-  return cli.waitFor(/break/)
+  return cli.waitForInitialBreak()
     .then(() => cli.waitForPrompt())
     .then(() => {
       t.match(cli.output, 'debug>', 'prints a prompt');
@@ -45,7 +45,7 @@ test('run after quit / restart', (t) => {
     throw error;
   }
 
-  return cli.waitFor(/break/)
+  return cli.waitForInitialBreak()
     .then(() => cli.waitForPrompt())
     .then(() => cli.stepCommand('n'))
     .then(() => {
diff --git a/test/cli/low-level.test.js b/test/cli/low-level.test.js
index b6301b2..966bed5 100644
--- a/test/cli/low-level.test.js
+++ b/test/cli/low-level.test.js
@@ -12,7 +12,7 @@ test('Debugger agent direct access', (t) => {
     throw error;
   }
 
-  return cli.waitFor(/break/)
+  return cli.waitForInitialBreak()
     .then(() => cli.waitForPrompt())
     .then(() => cli.command('scripts'))
     .then(() => {
diff --git a/test/cli/preserve-breaks.test.js b/test/cli/preserve-breaks.test.js
index 8de8227..17d7976 100644
--- a/test/cli/preserve-breaks.test.js
+++ b/test/cli/preserve-breaks.test.js
@@ -14,7 +14,7 @@ test('run after quit / restart', (t) => {
     throw error;
   }
 
-  return cli.waitFor(/break/)
+  return cli.waitForInitialBreak()
     .then(() => cli.waitForPrompt())
     .then(() => cli.command('breakpoints'))
     .then(() => {
diff --git a/test/cli/profile.test.js b/test/cli/profile.test.js
index 3ef1896..0f900c5 100644
--- a/test/cli/profile.test.js
+++ b/test/cli/profile.test.js
@@ -15,7 +15,7 @@ test('profiles', (t) => {
     throw error;
   }
 
-  return cli.waitFor(/break/)
+  return cli.waitForInitialBreak()
     .then(() => cli.waitForPrompt())
     .then(() => cli.command('exec console.profile()'))
     .then(() => {
diff --git a/test/cli/scripts.test.js b/test/cli/scripts.test.js
index cd26411..ed36705 100644
--- a/test/cli/scripts.test.js
+++ b/test/cli/scripts.test.js
@@ -14,7 +14,7 @@ test('list scripts', (t) => {
     throw error;
   }
 
-  return cli.waitFor(/break/)
+  return cli.waitForInitialBreak()
     .then(() => cli.waitForPrompt())
     .then(() => cli.command('scripts'))
     .then(() => {
diff --git a/test/cli/start-cli.js b/test/cli/start-cli.js
index 5a652e3..74c9481 100644
--- a/test/cli/start-cli.js
+++ b/test/cli/start-cli.js
@@ -93,6 +93,10 @@ function startCLI(args) {
       return this.waitFor(/>\s+$/, timeout);
     },
 
+    waitForInitialBreak(timeout = 2000) {
+      return this.waitFor(/break/i, timeout);
+    },
+
     ctrlC() {
       return this.command('.interrupt');
     },
diff --git a/test/cli/use-strict.test.js b/test/cli/use-strict.test.js
index 81f4d91..780802a 100644
--- a/test/cli/use-strict.test.js
+++ b/test/cli/use-strict.test.js
@@ -14,7 +14,7 @@ test('for whiles that starts with strict directive', (t) => {
     throw error;
   }
 
-  return cli.waitFor(/break/)
+  return cli.waitForInitialBreak()
     .then(() => cli.waitForPrompt())
     .then(() => {
       t.match(
diff --git a/test/cli/watchers.test.js b/test/cli/watchers.test.js
index d66f008..46bcde1 100644
--- a/test/cli/watchers.test.js
+++ b/test/cli/watchers.test.js
@@ -11,7 +11,7 @@ test('stepping through breakpoints', (t) => {
     throw error;
   }
 
-  return cli.waitFor(/break/)
+  return cli.waitForInitialBreak()
     .then(() => cli.waitForPrompt())
     .then(() => cli.command('watch("x")'))
     .then(() => cli.command('watch("\\"Hello\\"")'))