diff --git a/src/modules/AdvancedPaste/AdvancedPaste/Helpers/ClipboardHelper.cs b/src/modules/AdvancedPaste/AdvancedPaste/Helpers/ClipboardHelper.cs
index 4cfa524ad33..66ee7aa3e24 100644
--- a/src/modules/AdvancedPaste/AdvancedPaste/Helpers/ClipboardHelper.cs
+++ b/src/modules/AdvancedPaste/AdvancedPaste/Helpers/ClipboardHelper.cs
@@ -6,7 +6,6 @@
 using System.Threading;
 using System.Threading.Tasks;
 using ManagedCommon;
-using Microsoft.UI.Xaml.Media.Imaging;
 using Windows.ApplicationModel.DataTransfer;
 using Windows.Storage.Streams;
 using Windows.System;
@@ -21,9 +20,30 @@ internal static void SetClipboardTextContent(string text)
 
             if (!string.IsNullOrEmpty(text))
             {
+                Logger.LogDebug("Text to set to clipboard: " + text);
+
                 DataPackage output = new();
                 output.SetText(text);
-                Clipboard.SetContentWithOptions(output, null);
+                bool success = Clipboard.SetContentWithOptions(output, null);
+                Logger.LogDebug("Setting Clipboard data was success?: " + success);
+
+                // Wait 50 ms in a loop until setting the clipboard content has really finished.
+                while (!Clipboard.GetContent().GetTextAsync().GetAwaiter().GetResult().Contains(text))
+                {
+                    Thread.Sleep(50);
+                }
+
+#if DEBUG
+                try
+                {
+                    string clipContent = Clipboard.GetContent().GetTextAsync().GetAwaiter().GetResult();
+                    Logger.LogDebug("Clipboard content for current process: " + clipContent);
+                }
+                catch (Exception ex)
+                {
+                    Logger.LogError("Failed to get clipboard content: ", ex.GetBaseException());
+                }
+#endif
 
                 // TODO(stefan): For some reason Flush() fails from time to time when directly activated via hotkey.
                 // Calling inside a loop makes it work.
@@ -39,14 +59,24 @@ internal static void SetClipboardTextContent(string text)
                     {
                         Task.Run(() =>
                         {
-                            Clipboard.Flush();
+                            try
+                            {
+                                Clipboard.Flush();
+                            }
+                            catch (Exception ex)
+                            {
+                                Logger.LogError("Clipboard.Flush() failed. Real reason:", ex.GetBaseException());
+                                throw;
+                            }
                         }).Wait();
 
                         flushed = true;
+                        Logger.LogDebug("Clipboard flushed.");
                     }
                     catch (Exception ex)
                     {
                         Logger.LogError("Clipboard.Flush() failed", ex);
+                        Thread.Sleep(50);
                     }
                 }
             }
diff --git a/src/modules/AdvancedPaste/AdvancedPaste/ViewModels/OptionsViewModel.cs b/src/modules/AdvancedPaste/AdvancedPaste/ViewModels/OptionsViewModel.cs
index 894b8e5536a..60cdca1abe7 100644
--- a/src/modules/AdvancedPaste/AdvancedPaste/ViewModels/OptionsViewModel.cs
+++ b/src/modules/AdvancedPaste/AdvancedPaste/ViewModels/OptionsViewModel.cs
@@ -6,6 +6,7 @@
 using System.Collections.ObjectModel;
 using System.Globalization;
 using System.Net;
+using System.Threading;
 using System.Threading.Tasks;
 using AdvancedPaste.Helpers;
 using AdvancedPaste.Models;
@@ -252,6 +253,8 @@ internal void ToPlainTextFunction()
             {
                 Logger.LogTrace();
 
+                string originalClipboardData = ClipboardData.GetTextAsync().GetAwaiter().GetResult();
+
                 string outputString = MarkdownHelper.PasteAsPlainTextFromClipboard(ClipboardData);
 
                 SetClipboardContentAndHideWindow(outputString);
@@ -260,6 +263,13 @@ internal void ToPlainTextFunction()
                 {
                     ClipboardHelper.SendPasteKeyCombination();
                 }
+
+                // Sleeping 250 ms that paste command can be completely executed before resetting the clipboard.
+                // Otherwise we reset the clipboard to early and past the original content. Or the clipboard is still used while resetting and resetting fails.
+                Thread.Sleep(250);
+
+                // Resetting clipboard content
+                SetClipboardContentAndHideWindow(originalClipboardData);
             }
             catch
             {
@@ -272,6 +282,8 @@ internal void ToMarkdownFunction(bool pasteAlways = false)
             {
                 Logger.LogTrace();
 
+                string originalClipboardData = ClipboardData.GetTextAsync().GetAwaiter().GetResult();
+
                 string outputString = MarkdownHelper.ToMarkdown(ClipboardData);
 
                 SetClipboardContentAndHideWindow(outputString);
@@ -280,6 +292,13 @@ internal void ToMarkdownFunction(bool pasteAlways = false)
                 {
                     ClipboardHelper.SendPasteKeyCombination();
                 }
+
+                // Sleeping 250 ms that paste command can be completely executed before resetting the clipboard.
+                // Otherwise we reset the clipboard to early and past the original content. Or the clipboard is still used while resetting and resetting fails.
+                Thread.Sleep(250);
+
+                // Resetting clipboard content
+                SetClipboardContentAndHideWindow(originalClipboardData);
             }
             catch
             {
@@ -292,6 +311,8 @@ internal void ToJsonFunction(bool pasteAlways = false)
             {
                 Logger.LogTrace();
 
+                string originalClipboardData = ClipboardData.GetTextAsync().GetAwaiter().GetResult();
+
                 string jsonText = JsonHelper.ToJsonFromXmlOrCsv(ClipboardData);
 
                 SetClipboardContentAndHideWindow(jsonText);
@@ -300,6 +321,13 @@ internal void ToJsonFunction(bool pasteAlways = false)
                 {
                     ClipboardHelper.SendPasteKeyCombination();
                 }
+
+                // Sleeping 250 ms that paste command can be completely executed before resetting the clipboard.
+                // Otherwise we reset the clipboard to early and past the original content. Or the clipboard is still used while resetting and resetting fails.
+                Thread.Sleep(250);
+
+                // Resetting clipboard content
+                SetClipboardContentAndHideWindow(originalClipboardData);
             }
             catch
             {