diff --git a/lib/exile/process.ex b/lib/exile/process.ex
index 566f8a8..efe86af 100644
--- a/lib/exile/process.ex
+++ b/lib/exile/process.ex
@@ -340,6 +340,8 @@ defmodule Exile.Process do
 
   @type exit_status :: non_neg_integer
 
+  @type os_pid :: pos_integer
+
   @default_opts [env: [], stderr: :console]
   @default_buffer_size 65_535
   @os_signal_timeout 1000
@@ -595,7 +597,7 @@ defmodule Exile.Process do
   This is meant only for debugging. Avoid interacting with the
   external process directly
   """
-  @spec os_pid(t) :: pos_integer()
+  @spec os_pid(t) :: os_pid()
   def os_pid(process) do
     GenServer.call(process.pid, :os_pid, :infinity)
   end
@@ -626,6 +628,9 @@ defmodule Exile.Process do
     {:noreply, exec(state)}
   end
 
+  # certain programs expects SIGTERM multiple times
+  @exit_seq [:no_signal, :sigterm, :sigterm, :sigkill]
+
   @impl true
   def handle_cast({:prepare_exit, caller, timeout}, state) do
     state =
@@ -648,9 +653,9 @@ defmodule Exile.Process do
         if timeout == :infinity do
           {:noreply, state}
         else
-          total_stages = 3
-          stage_timeout = div(timeout, total_stages)
-          handle_info({:prepare_exit, :normal_exit, stage_timeout}, state)
+          timeout = div(timeout, length(@exit_seq))
+          exit_seq = Enum.map(@exit_seq, &{&1, timeout})
+          handle_info({:run_exit_sequence, exit_seq}, state)
         end
     end
   end
@@ -735,28 +740,24 @@ defmodule Exile.Process do
   end
 
   @impl true
-  def handle_info({:prepare_exit, current_stage, timeout}, %{status: status, port: port} = state) do
-    cond do
-      status != :running ->
+  def handle_info({:run_exit_sequence, exit_seq}, %{status: status, port: port} = state) do
+    case exit_seq do
+      _ when status != :running ->
+        # we are done if port is not running
         {:noreply, state}
 
-      current_stage == :normal_exit ->
-        Elixir.Process.send_after(self(), {:prepare_exit, :sigterm, timeout}, timeout)
-        {:noreply, state}
+      [] ->
+        # This should never happen, since SIGKILL signal can not be
+        # ignored by the OS process
+        {:stop, :kill_timeout, state}
 
-      current_stage == :sigterm ->
-        signal(port, :sigterm)
-        Elixir.Process.send_after(self(), {:prepare_exit, :sigkill, timeout}, timeout)
-        {:noreply, state}
+      [{signal, timeout} | exit_seq] ->
+        if signal != :no_signal do
+          signal(port, signal)
+        end
 
-      current_stage == :sigkill ->
-        signal(port, :sigkill)
-        Elixir.Process.send_after(self(), {:prepare_exit, :stop, timeout}, timeout)
+        Elixir.Process.send_after(self(), {:run_exit_sequence, exit_seq}, timeout)
         {:noreply, state}
-
-      # this should never happen, since sigkill signal can not be ignored by the OS process
-      current_stage == :stop ->
-        {:stop, :sigkill_timeout, state}
     end
   end
 
diff --git a/lib/exile/watcher.ex b/lib/exile/watcher.ex
index 7c8524b..4f9b334 100644
--- a/lib/exile/watcher.ex
+++ b/lib/exile/watcher.ex
@@ -24,17 +24,15 @@ defmodule Exile.Watcher do
   end
 
   @impl true
-  def handle_info({:DOWN, ref, :process, pid, _reason}, %{
-        pid: pid,
-        socket_path: socket_path,
-        os_pid: os_pid,
-        ref: ref
-      }) do
+  def handle_info({:DOWN, ref, :process, pid, _reason}, %{pid: pid, ref: ref} = state) do
+    %{socket_path: socket_path, os_pid: os_pid} = state
     _ = File.rm(socket_path)
-    # at max we wait for 50ms for program to exit
-    if process_exit?(os_pid, 50) do
-      :ok
-    else
+
+    # Ideally we should skip checking if program is alive if the Exile
+    # process is terminated with reason `:normal` But at the moment we
+    # unconditionally terminate, potentially with reason `:normal`
+    # when owner process exit expecting the watcher to do the cleanup
+    if !process_dead?(os_pid, 50) do
       attempt_graceful_exit(os_pid)
     end
 
@@ -46,37 +44,60 @@ defmodule Exile.Watcher do
   # when watcher is attempted to be killed, we forcefully kill external os process.
   # This can happen when beam receive SIGTERM
   def handle_info({:EXIT, _, reason}, %{pid: pid, socket_path: socket_path, os_pid: os_pid}) do
-    Logger.debug(fn -> "Watcher exiting. reason: #{inspect(reason)}" end)
+    Logger.debug("Watcher exiting. reason: #{inspect(reason)}")
     File.rm!(socket_path)
     Elixir.Process.exit(pid, :watcher_exit)
     attempt_graceful_exit(os_pid)
     {:stop, reason, nil}
   end
 
+  # certain programs such as older version of `parallel` expects
+  # multiple `SIGTERM` signals
+  @term_seq [sigterm: 150, sigterm: 100, sigkill: 100]
+
+  @spec attempt_graceful_exit(Exile.Process.os_pid()) :: :ok | no_return
   defp attempt_graceful_exit(os_pid) do
-    Logger.debug("Failed to stop external program gracefully. attempting SIGTERM")
-    Nif.nif_kill(os_pid, :sigterm)
-    process_exit?(os_pid, 100) && throw(:done)
-
-    Logger.debug("Failed to stop external program with SIGTERM. attempting SIGKILL")
-    Nif.nif_kill(os_pid, :sigkill)
-    process_exit?(os_pid, 200) && throw(:done)
-
-    Logger.error("failed to kill external process")
-    raise "Failed to kill external process"
-  catch
-    :done ->
-      Logger.debug(fn -> "External program exited successfully" end)
-  end
+    Logger.debug("Starting graceful termination sequence: #{inspect(@term_seq)}")
+
+    dead? =
+      Enum.reduce_while(@term_seq, false, fn {signal, wait_time}, _dead? ->
+        Nif.nif_kill(os_pid, signal)
 
-  defp process_exit?(os_pid), do: !Nif.nif_is_os_pid_alive(os_pid)
+        # check process_status first before going to sleep
+        if process_dead?(os_pid, wait_time) do
+          Logger.debug("External program terminated successfully with signal: #{signal}")
+          {:halt, true}
+        else
+          Logger.debug("Failed to stop with signal: #{signal}, wait_time: #{wait_time}")
+          {:cont, false}
+        end
+      end)
 
-  defp process_exit?(os_pid, timeout) do
-    if process_exit?(os_pid) do
+    if dead? do
+      :ok
+    else
+      Logger.error("Failed to kill external process, os_pid #{os_pid}")
+      raise "Failed to kill external process"
+    end
+  end
+
+  @spec process_dead?(Exile.Process.os_pid(), pos_integer) :: boolean
+  defp process_dead?(os_pid, wait_time) do
+    # check process_status first before going to sleep
+    if process_status(os_pid) == :dead do
       true
     else
-      :timer.sleep(timeout)
-      process_exit?(os_pid)
+      Elixir.Process.sleep(wait_time)
+      process_status(os_pid) == :dead
+    end
+  end
+
+  @spec process_status(Exile.Process.os_pid()) :: :alive | :dead
+  defp process_status(os_pid) do
+    if Nif.nif_is_os_pid_alive(os_pid) do
+      :alive
+    else
+      :dead
     end
   end
 end
diff --git a/test/exile/process_test.exs b/test/exile/process_test.exs
index fdb8909..3ee5be6 100644
--- a/test/exile/process_test.exs
+++ b/test/exile/process_test.exs
@@ -208,7 +208,7 @@ defmodule Exile.ProcessTest do
           assert os_process_alive?(os_pid)
 
           # ensure the script set the correct signal handlers (handlers to ignore signal)
-          assert {:ok, "ignored signals\n"} = Process.read(s)
+          assert {:ok, "ignored signals\n" <> _} = Process.read(s)
 
           # exit without waiting for the exile process
           {os_pid, s}