diff --git a/Dalamud/Interface/DragDrop/DragDropManager.cs b/Dalamud/Interface/DragDrop/DragDropManager.cs
index 2b1f79ed1..0bb7eac12 100644
--- a/Dalamud/Interface/DragDrop/DragDropManager.cs
+++ b/Dalamud/Interface/DragDrop/DragDropManager.cs
@@ -35,16 +35,17 @@ internal partial class DragDropManager : IDisposable, IDragDropManager, IService
     /// <summary> Gets a value indicating whether a valid external drag and drop is currently active and hovering over any FFXIV-related viewport. </summary>
     public bool IsDragging { get; private set; }
 
-    /// <summary> Gets a value indicating whether there are any files or directories currently being dragged. </summary>
-    public bool HasPaths { get; private set; }
+    /// <summary> Gets a value indicating whether there are any files or directories currently being dragged, or stored from the last drop. </summary>
+    public bool HasPaths
+        => this.Files.Count + this.Directories.Count > 0;
 
-    /// <summary> Gets the list of file paths currently being dragged from an external application over any FFXIV-related viewport. </summary>
+    /// <summary> Gets the list of file paths currently being dragged from an external application over any FFXIV-related viewport, or stored from the last drop. </summary>
     public IReadOnlyList<string> Files { get; private set; } = Array.Empty<string>();
 
-    /// <summary> Gets a set of all extensions available in the paths currently being dragged from an external application over any FFXIV-related viewport. </summary>
+    /// <summary> Gets a set of all extensions available in the paths currently being dragged from an external application over any FFXIV-related viewport or stored from the last drop. </summary>
     public IReadOnlySet<string> Extensions { get; private set; } = new HashSet<string>();
 
-    /// <summary> Gets the list of directory paths currently being dragged from an external application over any FFXIV-related viewport. </summary>
+    /// <summary> Gets the list of directory paths currently being dragged from an external application over any FFXIV-related viewport or stored from the last drop. </summary>
     public IReadOnlyList<string> Directories { get; private set; } = Array.Empty<string>();
 
     /// <summary> Enable external drag and drop. </summary>
@@ -96,7 +97,7 @@ internal partial class DragDropManager : IDisposable, IDragDropManager, IService
     /// <inheritdoc cref="IDragDropManager.CreateImGuiSource(string, Func{IDragDropManager, bool}, Func{IDragDropManager, bool})"/>
     public void CreateImGuiSource(string label, Func<IDragDropManager, bool> validityCheck, Func<IDragDropManager, bool> tooltipBuilder)
     {
-        if (!this.HasPaths && !this.IsDropping())
+        if (!this.IsDragging && !this.IsDropping())
         {
             return;
         }
@@ -120,7 +121,7 @@ internal partial class DragDropManager : IDisposable, IDragDropManager, IService
     {
         files = Array.Empty<string>();
         directories = Array.Empty<string>();
-        if (!this.IsDragging || !ImGui.BeginDragDropTarget())
+        if (!this.HasPaths || !ImGui.BeginDragDropTarget())
         {
             return false;
         }
diff --git a/Dalamud/Interface/DragDrop/DragDropTarget.cs b/Dalamud/Interface/DragDrop/DragDropTarget.cs
index a592991dd..b6bb9d237 100644
--- a/Dalamud/Interface/DragDrop/DragDropTarget.cs
+++ b/Dalamud/Interface/DragDrop/DragDropTarget.cs
@@ -2,6 +2,7 @@ using System;
 using System.Collections.Generic;
 using System.IO;
 using System.Linq;
+using System.Runtime.CompilerServices;
 using System.Runtime.InteropServices.ComTypes;
 using System.Text;
 
@@ -15,6 +16,7 @@ namespace Dalamud.Interface.DragDrop;
 internal partial class DragDropManager : DragDropManager.IDropTarget
 {
     private int lastUpdateFrame = -1;
+    private DragDropInterop.ModifierKeys lastKeyState = DragDropInterop.ModifierKeys.MK_NONE;
 
     /// <summary> Create the drag and drop formats we accept. </summary>
     private static FORMATETC FormatEtc =
@@ -37,7 +39,7 @@ internal partial class DragDropManager : DragDropManager.IDropTarget
     public void DragEnter(IDataObject pDataObj, uint grfKeyState, POINTL pt, ref uint pdwEffect)
     {
         this.IsDragging = true;
-        UpdateIo((DragDropInterop.ModifierKeys)grfKeyState, true);
+        this.lastKeyState = UpdateIo((DragDropInterop.ModifierKeys)grfKeyState, true);
 
         if (pDataObj.QueryGetData(ref FormatEtc) != 0)
         {
@@ -47,9 +49,9 @@ internal partial class DragDropManager : DragDropManager.IDropTarget
         {
             pdwEffect &= (uint)DragDropInterop.DropEffects.Copy;
             (this.Files, this.Directories) = this.GetPaths(pDataObj);
-            this.HasPaths = this.Files.Count + this.Directories.Count > 0;
             this.Extensions = this.Files.Select(Path.GetExtension).Where(p => !p.IsNullOrEmpty()).Distinct().ToHashSet();
         }
+
         Log.Debug("[DragDrop] Entering external Drag and Drop with {KeyState} at {PtX}, {PtY} and with {N} files.", (DragDropInterop.ModifierKeys)grfKeyState, pt.x, pt.y, this.Files.Count + this.Directories.Count);
     }
 
@@ -64,7 +66,7 @@ internal partial class DragDropManager : DragDropManager.IDropTarget
         if (frame != this.lastUpdateFrame)
         {
             this.lastUpdateFrame = frame;
-            UpdateIo((DragDropInterop.ModifierKeys)grfKeyState, false);
+            this.lastKeyState = UpdateIo((DragDropInterop.ModifierKeys)grfKeyState, false);
             pdwEffect &= (uint)DragDropInterop.DropEffects.Copy;
             Log.Verbose("[DragDrop] External Drag and Drop with {KeyState} at {PtX}, {PtY}.", (DragDropInterop.ModifierKeys)grfKeyState, pt.x, pt.y);
         }
@@ -87,10 +89,10 @@ internal partial class DragDropManager : DragDropManager.IDropTarget
     /// <param name="pdwEffect"> Effects that can be used with this drag and drop process. </param>
     public void Drop(IDataObject pDataObj, uint grfKeyState, POINTL pt, ref uint pdwEffect)
     {
-        MouseDrop((DragDropInterop.ModifierKeys)grfKeyState);
+        MouseDrop(this.lastKeyState);
         this.lastDropFrame = ImGui.GetFrameCount();
         this.IsDragging = false;
-        if (this.Files.Count > 0 || this.Directories.Count > 0)
+        if (this.HasPaths)
         {
             pdwEffect &= (uint)DragDropInterop.DropEffects.Copy;
         }
@@ -102,7 +104,7 @@ internal partial class DragDropManager : DragDropManager.IDropTarget
         Log.Debug("[DragDrop] Dropping {N} files with {KeyState} at {PtX}, {PtY}.", this.Files.Count + this.Directories.Count, (DragDropInterop.ModifierKeys)grfKeyState, pt.x, pt.y);
     }
 
-    private static void UpdateIo(DragDropInterop.ModifierKeys keys, bool entering)
+    private static DragDropInterop.ModifierKeys UpdateIo(DragDropInterop.ModifierKeys keys, bool entering)
     {
         var io = ImGui.GetIO();
         void UpdateMouse(int mouseIdx)
@@ -163,6 +165,8 @@ internal partial class DragDropManager : DragDropManager.IDropTarget
             io.KeyShift = false;
             io.AddKeyEvent(ImGuiKey.LeftShift, false);
         }
+
+        return keys;
     }
 
     private static void MouseDrop(DragDropInterop.ModifierKeys keys)