diff --git a/Makefile b/Makefile
index 2826148b..ee153c95 100644
--- a/Makefile
+++ b/Makefile
@@ -67,6 +67,11 @@ gem_build_install:
 gem_uninstall:
 	gem uninstall uffizzi-cli
 
+gem_reinstall:
+	ls -la | grep uffizzi-cli- | rm -f
+	make gem_uninstall
+	make gem_build_install
+
 brew_add_tap:
 	brew tap UffizziCloud/tap
 
diff --git a/lib/uffizzi.rb b/lib/uffizzi.rb
index 0326dad6..1b57c762 100644
--- a/lib/uffizzi.rb
+++ b/lib/uffizzi.rb
@@ -38,7 +38,19 @@ def root
     end
 
     def process
-      @process ||= Process
+      Process
+    end
+
+    def signal
+      Signal
+    end
+
+    def thread
+      Thread
+    end
+
+    def at_exit(&block)
+      Kernel.at_exit(&block)
     end
   end
 end
diff --git a/lib/uffizzi/cli/dev.rb b/lib/uffizzi/cli/dev.rb
index b96f48d0..40e52d38 100644
--- a/lib/uffizzi/cli/dev.rb
+++ b/lib/uffizzi/cli/dev.rb
@@ -222,8 +222,8 @@ def parse_kubeconfig(kubeconfig)
     def launch_demonise_skaffold(config_path)
       Uffizzi.process.daemon(true)
 
-      at_exit do
-        DevService.delete_pid
+      Uffizzi.at_exit do
+        DevService.stop_process
       end
 
       DevService.save_pid
@@ -235,8 +235,8 @@ def launch_demonise_skaffold(config_path)
     end
 
     def launch_basic_skaffold(config_path)
-      at_exit do
-        DevService.delete_pid
+      Uffizzi.at_exit do
+        DevService.stop_process
       end
 
       DevService.save_pid
diff --git a/lib/uffizzi/services/dev_service.rb b/lib/uffizzi/services/dev_service.rb
index b47558b5..61caf485 100644
--- a/lib/uffizzi/services/dev_service.rb
+++ b/lib/uffizzi/services/dev_service.rb
@@ -32,13 +32,27 @@ def stop_process
       dev_pid = running_pid
       skaffold_pid = running_skaffold_pid
 
-      Uffizzi.process.kill('INT', skaffold_pid)
-      Uffizzi.process.kill('INT', dev_pid)
+      begin
+        Uffizzi.process.kill('INT', skaffold_pid)
+      rescue Errno::ESRCH
+      end
+
+      wait_process_stop(skaffold_pid)
       delete_pid
+
+      Uffizzi.process.kill('INT', dev_pid)
     rescue Errno::ESRCH
       delete_pid
     end
 
+    def wait_process_stop(pid)
+      loop do
+        Uffizzi.process.kill(0, pid)
+        sleep(1)
+      end
+    rescue Errno::ESRCH
+    end
+
     def process_running?
       pid = running_pid
       return false unless pid.positive?
@@ -50,9 +64,9 @@ def process_running?
     end
 
     def start_check_pid_file_existence
-      Thread.new do
+      Uffizzi.thread.new do
         loop do
-          Uffizzi.process.kill('QUIT', Uffizzi.process.pid) unless File.exist?(pid_path)
+          stop_process unless File.exist?(pid_path)
           sleep(1)
         end
       end
@@ -62,6 +76,8 @@ def start_basic_skaffold(config_path, options)
       Uffizzi.ui.say('Start skaffold')
       cmd = build_skaffold_dev_command(config_path, options)
 
+      Uffizzi.signal.trap('INT') {}
+
       Uffizzi.ui.popen2e(cmd) do |_stdin, stdout_and_stderr, wait_thr|
         pid = wait_thr.pid
         skaffold_pid = find_skaffold_pid(pid)
@@ -198,13 +214,29 @@ def dev_environment
       Uffizzi::ConfigHelper.dev_environment
     end
 
-    def find_skaffold_pid(ppid)
-      ppid_regex = /\w*\s+\d+\s+#{ppid}.*\sskaffold dev/
-      pid_regex = /\w*\s+(\d+)\s+#{ppid}.*\sskaffold dev/
-
+    def find_skaffold_pid(pid)
+      pid_regex = /\w*#{pid}.*skaffold dev/
       io = Uffizzi.ui.popen('ps -ef')
-      ps = io.readlines.detect { |l| l.match?(ppid_regex) }
-      ps.match(pid_regex)[1]
+      processes = io.readlines.select { |l| l.match?(pid_regex) }
+
+      if processes.count.zero?
+        raise StandardError.new('Can\'t find skaffold process pid')
+      end
+
+      # HACK: For MacOS
+      if processes.count == 1
+        current_pid = processes[0].gsub(/\s+/, ' ').lstrip.split[1]
+        return pid if current_pid.to_s == pid.to_s
+
+        raise StandardError.new('Can\'t find skaffold process pid')
+      end
+
+      # HACK: For Linux
+      parent_process = processes
+        .map { |ps| ps.gsub(/\s+/, ' ').lstrip.split }
+        .detect { |ps| ps[2].to_s == pid.to_s }
+
+      parent_process[1]
     end
   end
 end
diff --git a/test/support/mocks/mock_prompt.rb b/test/support/mocks/mock_prompt.rb
index 1051317d..7882e213 100644
--- a/test/support/mocks/mock_prompt.rb
+++ b/test/support/mocks/mock_prompt.rb
@@ -38,7 +38,6 @@ def promise_question_answer(question, answer)
 
   def get_answer(question)
     answer_index = @question_answers.index do |question_answer|
-      question_answer[:question] == question
       case question_answer[:question]
       when Regexp
         question_answer[:question].match?(question)
diff --git a/test/support/mocks/mock_signal.rb b/test/support/mocks/mock_signal.rb
new file mode 100644
index 00000000..d0f4c029
--- /dev/null
+++ b/test/support/mocks/mock_signal.rb
@@ -0,0 +1,7 @@
+# frozen_string_literal: true
+
+class MockSignal
+  class << self
+    def trap(_sig); end
+  end
+end
diff --git a/test/support/mocks/mock_thread.rb b/test/support/mocks/mock_thread.rb
new file mode 100644
index 00000000..a63a887a
--- /dev/null
+++ b/test/support/mocks/mock_thread.rb
@@ -0,0 +1,5 @@
+# frozen_string_literal: true
+
+class MockThread
+  def initialize; end
+end
diff --git a/test/test_helper.rb b/test/test_helper.rb
index 6e1b81b7..cf8ee0eb 100644
--- a/test/test_helper.rb
+++ b/test/test_helper.rb
@@ -37,7 +37,7 @@ class Minitest::Test
   TEST_CONFIG_DIR = 'tmp/config_default.json'
   TEST_TOKEN_PATH = 'tmp/token_default.json'
   TEST_PID_PATH = 'tmp/dev.pid'
-  TEST_PID_PATH = 'tmp/skaffold_dev.pid'
+  TEST_SKAFFOLD_PID_PATH = 'tmp/skaffold_dev.pid'
   TEST_DEV_LOGS_PATH = 'tmp/dev-logs.txt'
 
   def before_setup
@@ -49,11 +49,14 @@ def before_setup
     Uffizzi.stubs(:ui).returns(@mock_shell)
     Uffizzi.stubs(:prompt).returns(@mock_prompt)
     Uffizzi.stubs(:process).returns(@mock_process)
+    Uffizzi.stubs(:signal).returns(MockSignal)
+    Uffizzi.stubs(:thread).returns(MockSignal)
+    Uffizzi.stubs(:at_exit).returns(nil)
     Uffizzi::ConfigFile.stubs(:config_path).returns(TEST_CONFIG_PATH)
     Uffizzi::Token.stubs(:token_path).returns(TEST_TOKEN_PATH)
     Uffizzi::ConfigFile.stubs(:config_path).returns(TEST_CONFIG_PATH)
     DevService.stubs(:pid_path).returns(TEST_PID_PATH)
-    DevService.stubs(:skaffold_pid_path).returns(TEST_PID_PATH)
+    DevService.stubs(:skaffold_pid_path).returns(TEST_SKAFFOLD_PID_PATH)
     DevService.stubs(:logs_path).returns(TEST_DEV_LOGS_PATH)
   end
 
@@ -70,6 +73,7 @@ def before_teardown
     File.delete(TEST_CONFIG_PATH) if File.exist?(TEST_CONFIG_PATH)
     File.delete(TEST_TOKEN_PATH) if File.exist?(TEST_TOKEN_PATH)
     File.delete(TEST_PID_PATH) if File.exist?(TEST_PID_PATH)
+    File.delete(TEST_SKAFFOLD_PID_PATH) if File.exist?(TEST_SKAFFOLD_PID_PATH)
     File.delete(TEST_DEV_LOGS_PATH) if File.exist?(TEST_DEV_LOGS_PATH)
   end