diff --git a/exe/retest b/exe/retest
index da14480f..a30cc2d9 100755
--- a/exe/retest
+++ b/exe/retest
@@ -13,13 +13,15 @@ if options.help?
   return
 end
 
-repository = Retest::Repository.new(files: Retest::VersionControl.files)
+prompt     = Retest::Prompt.new
+repository = Retest::Repository.new(files: Retest::VersionControl.files, prompt: prompt)
 command    = Retest::Command.for_options(options)
 runner     = Retest::Runners.runner_for(command.to_s)
 sounds     = Retest::Sounds.for(options)
 
 sounds.play(:start)
 runner.add_observer(sounds)
+prompt.add_observer(sounds)
 
 program = Retest::Program.new(
   repository: repository,
diff --git a/lib/retest/prompt.rb b/lib/retest/prompt.rb
index 54dd92dc..2409f4a3 100644
--- a/lib/retest/prompt.rb
+++ b/lib/retest/prompt.rb
@@ -1,5 +1,7 @@
 module Retest
   class Prompt
+    include Observable
+
     def self.ask_which_test_to_use(path, files)
       new.ask_which_test_to_use(path, files)
     end
@@ -15,6 +17,9 @@ def initialize(input: nil, output: nil)
     end
 
     def ask_which_test_to_use(path, files)
+      changed
+      notify_observers(:question)
+
       output.puts(<<~QUESTION)
         We found few tests matching: #{path}
 
diff --git a/lib/retest/sounds.rb b/lib/retest/sounds.rb
index 9a59e22a..ab76b825 100644
--- a/lib/retest/sounds.rb
+++ b/lib/retest/sounds.rb
@@ -26,6 +26,8 @@ def play(sound)
           ['afplay', '/System/Library/Sounds/Funk.aiff']
         when :start
           ['afplay', '/System/Library/Sounds/Blow.aiff']
+        when :question
+          ['afplay', '/System/Library/Sounds/Glass.aiff']
         else
           raise ArgumentError.new("No sounds were found for type: #{sound}.")
         end
@@ -40,15 +42,18 @@ def play(sound)
 # List of Mac Audio Files:
 # afplay /System/Library/Sounds/Basso.aiff
 # afplay /System/Library/Sounds/Bottle.aiff
-# afplay /System/Library/Sounds/Funk.aiff
 # afplay /System/Library/Sounds/Hero.aiff
 # afplay /System/Library/Sounds/Ping.aiff
 # afplay /System/Library/Sounds/Purr.aiff
 # afplay /System/Library/Sounds/Submarine.aiff
-# afplay /System/Library/Sounds/Blow.aiff
 # afplay /System/Library/Sounds/Frog.aiff
-# afplay /System/Library/Sounds/Glass.aiff
 # afplay /System/Library/Sounds/Morse.aiff
 # afplay /System/Library/Sounds/Pop.aiff
-# afplay /System/Library/Sounds/Sosumi.aiff
 # afplay /System/Library/Sounds/Tink.aiff
+
+# USED
+
+# fail:     afplay /System/Library/Sounds/Sosumi.aiff
+# pass:     afplay /System/Library/Sounds/Funk.aiff
+# start:    afplay /System/Library/Sounds/Blow.aiff
+# question: afplay /System/Library/Sounds/Glass.aiff
\ No newline at end of file
diff --git a/test/retest/sounds/mac_os_test.rb b/test/retest/sounds/mac_os_test.rb
index fdda660e..a0b4179c 100644
--- a/test/retest/sounds/mac_os_test.rb
+++ b/test/retest/sounds/mac_os_test.rb
@@ -33,6 +33,24 @@ def test_play_tests_fail
 
         kernel.verify
       end
+
+      def test_play_question
+        kernel = MiniTest::Mock.new
+        kernel.expect(:system, true, ['afplay', '/System/Library/Sounds/Glass.aiff'])
+
+        MacOS.new(kernel: kernel, thread: FakeThread).play(:question)
+
+        kernel.verify
+      end
+
+      def test_play_start
+        kernel = MiniTest::Mock.new
+        kernel.expect(:system, true, ['afplay', '/System/Library/Sounds/Blow.aiff'])
+
+        MacOS.new(kernel: kernel, thread: FakeThread).play(:start)
+
+        kernel.verify
+      end
     end
   end
 end