diff --git a/src/modules/espresso/Espresso.Shell/Core/APIHelper.cs b/src/modules/espresso/Espresso.Shell/Core/APIHelper.cs
index 3d5b29b4a8..f7383b3b3c 100644
--- a/src/modules/espresso/Espresso.Shell/Core/APIHelper.cs
+++ b/src/modules/espresso/Espresso.Shell/Core/APIHelper.cs
@@ -4,6 +4,8 @@
 
 using System;
 using System.Runtime.InteropServices;
+using System.Threading;
+using System.Threading.Tasks;
 
 namespace Espresso.Shell.Core
 {
@@ -22,6 +24,9 @@ namespace Espresso.Shell.Core
     /// </summary>
     public class APIHelper
     {
+        private static CancellationTokenSource TokenSource = new CancellationTokenSource();
+        private static CancellationToken ThreadToken;
+
         // More details about the API used: https://docs.microsoft.com/windows/win32/api/winbase/nf-winbase-setthreadexecutionstate
         [DllImport("kernel32.dll", CharSet = CharSet.Auto, SetLastError = true)]
         static extern EXECUTION_STATE SetThreadExecutionState(EXECUTION_STATE esFlags);
@@ -58,6 +63,7 @@ namespace Espresso.Shell.Core
 
         public static bool SetNormalKeepAwake()
         {
+            //TokenSource.Cancel();
             return SetAwakeState(EXECUTION_STATE.ES_CONTINUOUS);
         }
 
@@ -73,43 +79,74 @@ namespace Espresso.Shell.Core
             }    
         }
 
-        public static bool SetTimedKeepAwake(long seconds, bool keepDisplayOn = true)
+        public static void SetTimedKeepAwake(long seconds, Action<bool> callback, bool keepDisplayOn = true)
         {
+            ThreadToken = TokenSource.Token;
+
+            try
+            {
+                Task.Run(() => RunTimedLoop(seconds, keepDisplayOn), ThreadToken).ContinueWith((result) => callback(result.Result));
+            }
+            catch (OperationCanceledException e)
+            {
+                Console.WriteLine($"{nameof(OperationCanceledException)} thrown with message: {e.Message}");
+            }
+            finally
+            {
+                TokenSource.Dispose();
+            }
+
+        }
+
+        private static bool RunTimedLoop(long seconds, bool keepDisplayOn = true)
+        {
+            bool success;
+
+            // In case cancellation was already requested.
+            //ThreadToken.ThrowIfCancellationRequested();
+
             if (keepDisplayOn)
             {
-                var success = SetAwakeState(EXECUTION_STATE.ES_SYSTEM_REQUIRED | EXECUTION_STATE.ES_DISPLAY_REQUIRED | EXECUTION_STATE.ES_CONTINUOUS);
+                success = SetAwakeState(EXECUTION_STATE.ES_SYSTEM_REQUIRED | EXECUTION_STATE.ES_DISPLAY_REQUIRED | EXECUTION_STATE.ES_CONTINUOUS);
                 if (success)
                 {
-                    RunTimedLoop(seconds);
-                    return true;
+                    Console.WriteLine("Timed keep-awake with display on.");
+                    var startTime = DateTime.UtcNow;
+                    while (DateTime.UtcNow - startTime < TimeSpan.FromSeconds(seconds))
+                    {
+                        if (ThreadToken.IsCancellationRequested)
+                        {
+                            ThreadToken.ThrowIfCancellationRequested();
+                        }
+                    }
+                    return success;
                 }
                 else
                 {
-                    return false;
+                    return success;
                 }
             }
             else
             {
-                var success = SetAwakeState(EXECUTION_STATE.ES_SYSTEM_REQUIRED | EXECUTION_STATE.ES_CONTINUOUS);
+                success = SetAwakeState(EXECUTION_STATE.ES_SYSTEM_REQUIRED | EXECUTION_STATE.ES_CONTINUOUS);
                 if (success)
                 {
-                    RunTimedLoop(seconds);
-                    return true;
+                    Console.WriteLine("Timed keep-awake with display off.");
+                    var startTime = DateTime.UtcNow;
+                    while (DateTime.UtcNow - startTime < TimeSpan.FromSeconds(seconds))
+                    {
+                        if (ThreadToken.IsCancellationRequested)
+                        {
+                            ThreadToken.ThrowIfCancellationRequested();
+                        }
+                    }
+                    return success;
                 }
                 else
                 {
-                    return false;
+                    return success;
                 }
             }
         }
-
-        private static void RunTimedLoop(long seconds)
-        {
-            var startTime = DateTime.UtcNow;
-            while (DateTime.UtcNow - startTime < TimeSpan.FromSeconds(seconds))
-            {
-                // We do nothing.
-            }
-        }
     }
 }
diff --git a/src/modules/espresso/Espresso.Shell/Program.cs b/src/modules/espresso/Espresso.Shell/Program.cs
index a6807f5c3f..a44d21c98a 100644
--- a/src/modules/espresso/Espresso.Shell/Program.cs
+++ b/src/modules/espresso/Espresso.Shell/Program.cs
@@ -141,20 +141,20 @@ namespace Espresso.Shell
                 else
                 {
                     // Timed keep-awake.
-                    bool success = APIHelper.SetTimedKeepAwake(timeLimit, displayOn);
-                    if (success)
-                    {
-                        Console.WriteLine($"Finished execution of timed keep-awake.");
+                    APIHelper.SetTimedKeepAwake(timeLimit, LogTimedKeepAwakeCompletion, displayOn);
+                    //if (success)
+                    //{
+                    //    Console.WriteLine($"Finished execution of timed keep-awake.");
 
-                        // Because the timed keep-awake execution completed, there is no reason for
-                        // Espresso to stay alive - I will just shut down the application until it's
-                        // launched again by the user.
-                        Environment.Exit(0);
-                    }
-                    else
-                    {
-                        Console.WriteLine("Could not set up the state to be timed keep awake.");
-                    }
+                    //    // Because the timed keep-awake execution completed, there is no reason for
+                    //    // Espresso to stay alive - I will just shut down the application until it's
+                    //    // launched again by the user.
+                    //    Environment.Exit(0);
+                    //}
+                    //else
+                    //{
+                    //    Console.WriteLine("Could not set up the state to be timed keep awake.");
+                    //}
                 }
             }
 
@@ -163,6 +163,8 @@ namespace Espresso.Shell
 
         private static void HandleEspressoConfigChange(object sender, FileSystemEventArgs e)
         {
+            Console.WriteLine("Resetting keep-awake to normal state due to settings change.");
+            ResetNormalPowerState();
             Console.WriteLine("Detected a file change. Reacting...");
             ProcessSettings(e.FullPath);
         }
@@ -210,22 +212,22 @@ namespace Espresso.Shell
                                     long computedTime = (settings.Properties.Hours.Value * 60 * 60) + (settings.Properties.Minutes.Value * 60);
                                     Console.WriteLine($"In timed keep-awake mode. Expecting to be awake for {computedTime} seconds.");
 
-                                    bool success = APIHelper.SetTimedKeepAwake(computedTime, settings.Properties.KeepDisplayOn.Value);
-                                    if (success)
-                                    {
-                                        Console.WriteLine($"Finished execution of timed keep-awake.");
+                                    APIHelper.SetTimedKeepAwake(computedTime, LogTimedKeepAwakeCompletion, settings.Properties.KeepDisplayOn.Value);
+                                    //if (success)
+                                    //{
+                                    //    Console.WriteLine($"Finished execution of timed keep-awake.");
 
-                                        ResetNormalPowerState();
-                                    }
-                                    else
-                                    {
-                                        Console.WriteLine("Could not set up the state to be timed keep awake.");
-                                    }
+                                    //    ResetNormalPowerState();
+                                    //}
+                                    //else
+                                    //{
+                                    //    Console.WriteLine("Could not set up the state to be timed keep awake.");
+                                    //}
                                     break;
                                 }
                             default:
                                 {
-                                    ForceExit("Could not select the right mode of operation. Existing...", 1);
+                                    Console.WriteLine("Unknown mode of operation. Check config file.");
                                     break;
                                 }
                         }
@@ -246,6 +248,11 @@ namespace Espresso.Shell
             }
         }
 
+        private static void LogTimedKeepAwakeCompletion(bool result)
+        {
+            Console.Write($"Completed timed keep-awake successfully: {result}");
+        }
+
         private static void ResetNormalPowerState()
         {
             bool success = APIHelper.SetNormalKeepAwake();