diff --git a/src/modules/espresso/Espresso.Shell/Core/APIHelper.cs b/src/modules/espresso/Espresso.Shell/Core/APIHelper.cs
index 43682c2f1c..12454cafbf 100644
--- a/src/modules/espresso/Espresso.Shell/Core/APIHelper.cs
+++ b/src/modules/espresso/Espresso.Shell/Core/APIHelper.cs
@@ -91,52 +91,60 @@ namespace Espresso.Shell.Core
 
         private static bool RunTimedLoop(long seconds, bool keepDisplayOn = true)
         {
-            bool success;
+            bool success = false;
 
             // In case cancellation was already requested.
             //ThreadToken.ThrowIfCancellationRequested();
 
-            if (keepDisplayOn)
+            try
             {
-                success = SetAwakeState(EXECUTION_STATE.ES_SYSTEM_REQUIRED | EXECUTION_STATE.ES_DISPLAY_REQUIRED | EXECUTION_STATE.ES_CONTINUOUS);
-                if (success)
+                if (keepDisplayOn)
                 {
-                    Console.WriteLine("Timed keep-awake with display on.");
-                    var startTime = DateTime.UtcNow;
-                    while (DateTime.UtcNow - startTime < TimeSpan.FromSeconds(seconds))
+                    success = SetAwakeState(EXECUTION_STATE.ES_SYSTEM_REQUIRED | EXECUTION_STATE.ES_DISPLAY_REQUIRED | EXECUTION_STATE.ES_CONTINUOUS);
+                    if (success)
                     {
-                        if (ThreadToken.IsCancellationRequested)
+                        Console.WriteLine("Timed keep-awake with display on.");
+                        var startTime = DateTime.UtcNow;
+                        while (DateTime.UtcNow - startTime < TimeSpan.FromSeconds(seconds))
                         {
-                            ThreadToken.ThrowIfCancellationRequested();
+                            if (ThreadToken.IsCancellationRequested)
+                            {
+                                ThreadToken.ThrowIfCancellationRequested();
+                            }
                         }
+                        return success;
+                    }
+                    else
+                    {
+                        return success;
                     }
-                    return success;
                 }
                 else
                 {
-                    return success;
+                    success = SetAwakeState(EXECUTION_STATE.ES_SYSTEM_REQUIRED | EXECUTION_STATE.ES_CONTINUOUS);
+                    if (success)
+                    {
+                        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 success;
+                    }
                 }
             }
-            else
+            catch (OperationCanceledException ex)
             {
-                success = SetAwakeState(EXECUTION_STATE.ES_SYSTEM_REQUIRED | EXECUTION_STATE.ES_CONTINUOUS);
-                if (success)
-                {
-                    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 success;
-                }
+                // Task was clearly cancelled.
+                return success;
             }
         }
     }
diff --git a/src/modules/espresso/Espresso.Shell/Espresso.Shell.csproj b/src/modules/espresso/Espresso.Shell/Espresso.Shell.csproj
index fcef0fe5b7..6c3fac8cd6 100644
--- a/src/modules/espresso/Espresso.Shell/Espresso.Shell.csproj
+++ b/src/modules/espresso/Espresso.Shell/Espresso.Shell.csproj
@@ -8,6 +8,7 @@
   <ItemGroup>
     <PackageReference Include="Newtonsoft.Json" Version="13.0.1" />
     <PackageReference Include="System.CommandLine" Version="2.0.0-beta1.20071.2" />
+    <PackageReference Include="System.Runtime.Caching" Version="6.0.0-preview.1.21102.12" />
   </ItemGroup>
 
 </Project>
diff --git a/src/modules/espresso/Espresso.Shell/Program.cs b/src/modules/espresso/Espresso.Shell/Program.cs
index 9f4f7624c1..abb0f1cf42 100644
--- a/src/modules/espresso/Espresso.Shell/Program.cs
+++ b/src/modules/espresso/Espresso.Shell/Program.cs
@@ -9,6 +9,7 @@ using System;
 using System.CommandLine;
 using System.CommandLine.Invocation;
 using System.IO;
+using System.Runtime.Caching;
 using System.Threading;
 
 namespace Espresso.Shell
@@ -20,6 +21,10 @@ namespace Espresso.Shell
         private static FileSystemWatcher watcher = null;
         public static Mutex Mutex { get => mutex; set => mutex = value; }
 
+        private static MemoryCache _memoryCache;
+        private static CacheItemPolicy _cacheItemPolicy;
+        private const int CacheExpirationTimeframe = 500;
+
         static int Main(string[] args)
         {
             bool instantiated;
@@ -104,13 +109,21 @@ namespace Espresso.Shell
 
                 try
                 {
+                    _memoryCache = MemoryCache.Default;
+
                     watcher = new FileSystemWatcher
                     {
                         Path = Path.GetDirectoryName(config),
                         EnableRaisingEvents = true,
-                        NotifyFilter = NotifyFilters.LastWrite | NotifyFilters.Size,
+                        NotifyFilter = NotifyFilters.LastWrite,
                         Filter = Path.GetFileName(config)
                     };
+
+                    _cacheItemPolicy = new CacheItemPolicy()
+                    {
+                        RemovedCallback = HandleCacheRemoval
+                    };
+                    
                     watcher.Changed += new FileSystemEventHandler(HandleEspressoConfigChange);
 
                     // Initially the file might not be updated, so we need to start processing
@@ -147,12 +160,21 @@ namespace Espresso.Shell
             new ManualResetEvent(false).WaitOne();
         }
 
-        private static void HandleEspressoConfigChange(object sender, FileSystemEventArgs e)
+        private static void HandleCacheRemoval(CacheEntryRemovedArguments args)
         {
+            if (args.RemovedReason != CacheEntryRemovedReason.Expired) return;
+
+            var fileEvent = (FileSystemEventArgs)args.CacheItem.Value;
             Console.WriteLine("Resetting keep-awake to normal state due to settings change.");
             ResetNormalPowerState();
             Console.WriteLine("Detected a file change. Reacting...");
-            ProcessSettings(e.FullPath);
+            ProcessSettings(fileEvent.FullPath);
+        }
+
+        private static void HandleEspressoConfigChange(object sender, FileSystemEventArgs e)
+        {
+            _cacheItemPolicy.AbsoluteExpiration = DateTimeOffset.Now.AddMilliseconds(CacheExpirationTimeframe);
+            _memoryCache.AddOrGetExisting(e.Name, e, _cacheItemPolicy);
         }
 
         private static void ProcessSettings(string fullPath)