diff --git a/ShareX.HelpersLib/Enums.cs b/ShareX.HelpersLib/Enums.cs
index 09711498e..f66d7d852 100644
--- a/ShareX.HelpersLib/Enums.cs
+++ b/ShareX.HelpersLib/Enums.cs
@@ -36,6 +36,14 @@ public enum EDataType
         URL
     }
 
+    public enum EClipboardContentType
+    {
+        Default,
+        Image,
+        Text,
+        Files
+    }
+
     public enum PNGBitDepth // Localized
     {
         Default,
diff --git a/ShareX.HelpersLib/Forms/ClipboardContentViewer.cs b/ShareX.HelpersLib/Forms/ClipboardContentViewer.cs
index ef315a1aa..65e8ce8b2 100644
--- a/ShareX.HelpersLib/Forms/ClipboardContentViewer.cs
+++ b/ShareX.HelpersLib/Forms/ClipboardContentViewer.cs
@@ -35,6 +35,8 @@ public partial class ClipboardContentViewer : Form
     {
         public bool IsClipboardContentValid { get; private set; }
         public bool DontShowThisWindow { get; private set; }
+        public EClipboardContentType ClipboardContentType { get; private set; }
+        public object ClipboardContent { get; private set; }
 
         public ClipboardContentViewer(bool showCheckBox = false)
         {
@@ -59,6 +61,8 @@ private bool CheckClipboardContents()
                 {
                     if (img != null)
                     {
+                        ClipboardContentType = EClipboardContentType.Image;
+                        ClipboardContent = img.Clone();
                         pbClipboard.LoadImage(img);
                         pbClipboard.Visible = true;
                         lblQuestion.Text = string.Format(Resources.ClipboardContentViewer_ClipboardContentViewer_Load_Clipboard_content__Image__Size___0_x_1__, img.Width, img.Height);
@@ -72,6 +76,8 @@ private bool CheckClipboardContents()
 
                 if (!string.IsNullOrEmpty(text))
                 {
+                    ClipboardContentType = EClipboardContentType.Text;
+                    ClipboardContent = text;
                     txtClipboard.Text = text;
                     txtClipboard.Visible = true;
                     lblQuestion.Text = string.Format(Resources.ClipboardContentViewer_ClipboardContentViewer_Load_Clipboard_content__Text__Length___0__, text.Length);
@@ -84,6 +90,8 @@ private bool CheckClipboardContents()
 
                 if (files.Length > 0)
                 {
+                    ClipboardContentType = EClipboardContentType.Files;
+                    ClipboardContent = files;
                     lbClipboard.Items.AddRange(files);
                     lbClipboard.Visible = true;
                     lblQuestion.Text = string.Format(Resources.ClipboardContentViewer_ClipboardContentViewer_Load_Clipboard_content__File__Count___0__, files.Length);
diff --git a/ShareX/UploadManager.cs b/ShareX/UploadManager.cs
index 901d742e1..03e956129 100644
--- a/ShareX/UploadManager.cs
+++ b/ShareX/UploadManager.cs
@@ -211,6 +211,74 @@ public static void ClipboardUpload(TaskSettings taskSettings = null)
             }
         }
 
+        public static void ClipboardUploadCached(ClipboardContentViewer ccv, TaskSettings taskSettings = null)
+        {
+            if (taskSettings == null) taskSettings = TaskSettings.GetDefaultTaskSettings();
+
+            if (ccv.ClipboardContentType == EClipboardContentType.Image)
+            {
+                Image img = (Image)ccv.ClipboardContent;
+
+                if (img != null)
+                {
+                    if (!taskSettings.AdvancedSettings.ProcessImagesDuringClipboardUpload)
+                    {
+                        taskSettings.AfterCaptureJob = AfterCaptureTasks.UploadImageToHost;
+                    }
+
+                    RunImageTask(img, taskSettings);
+                }
+            }
+            else if (ccv.ClipboardContentType == EClipboardContentType.Text)
+            {
+                string text = (string)ccv.ClipboardContent;
+
+                if (!string.IsNullOrEmpty(text))
+                {
+                    string url = text.Trim();
+
+                    if (URLHelpers.IsValidURL(url))
+                    {
+                        if (taskSettings.UploadSettings.ClipboardUploadURLContents)
+                        {
+                            DownloadAndUploadFile(url, taskSettings);
+                            return;
+                        }
+
+                        if (taskSettings.UploadSettings.ClipboardUploadShortenURL)
+                        {
+                            ShortenURL(url, taskSettings);
+                            return;
+                        }
+
+                        if (taskSettings.UploadSettings.ClipboardUploadShareURL)
+                        {
+                            ShareURL(url, taskSettings);
+                            return;
+                        }
+                    }
+
+                    if (taskSettings.UploadSettings.ClipboardUploadAutoIndexFolder && text.Length <= 260 && Directory.Exists(text))
+                    {
+                        IndexFolder(text, taskSettings);
+                    }
+                    else
+                    {
+                        UploadText(text, taskSettings, true);
+                    }
+                }
+            }
+            else if (ccv.ClipboardContentType == EClipboardContentType.Files)
+            {
+                string[] files = (string[])ccv.ClipboardContent;
+
+                if (files.Length > 0)
+                {
+                    UploadFile(files, taskSettings);
+                }
+            }
+        }
+
         public static void ClipboardUploadWithContentViewer(TaskSettings taskSettings = null)
         {
             if (taskSettings == null) taskSettings = TaskSettings.GetDefaultTaskSettings();
@@ -219,7 +287,14 @@ public static void ClipboardUploadWithContentViewer(TaskSettings taskSettings =
             {
                 if (ccv.ShowDialog() == DialogResult.OK && ccv.IsClipboardContentValid)
                 {
-                    ClipboardUpload(taskSettings);
+                    if (ccv.ClipboardContentType != EClipboardContentType.Default)
+                    {
+                        ClipboardUploadCached(ccv, taskSettings);
+                    }
+                    else
+                    {
+                        ClipboardUpload(taskSettings);
+                    }
                 }
             }
         }
@@ -234,7 +309,14 @@ public static void ClipboardUploadMainWindow(TaskSettings taskSettings = null)
                 {
                     if (ccv.ShowDialog() == DialogResult.OK && ccv.IsClipboardContentValid)
                     {
-                        ClipboardUpload(taskSettings);
+                        if (ccv.ClipboardContentType != EClipboardContentType.Default)
+                        {
+                            ClipboardUploadCached(ccv, taskSettings);
+                        }
+                        else
+                        {
+                            ClipboardUpload(taskSettings);
+                        }
                     }
 
                     Program.Settings.ShowClipboardContentViewer = !ccv.DontShowThisWindow;