diff --git a/app/MindWork AI Studio/Components/AttachDocuments.razor b/app/MindWork AI Studio/Components/AttachDocuments.razor
index aea32e75..bc66f9c2 100644
--- a/app/MindWork AI Studio/Components/AttachDocuments.razor	
+++ b/app/MindWork AI Studio/Components/AttachDocuments.razor	
@@ -68,9 +68,9 @@ else
     </MudStack>
     <div @onmouseenter="@this.OnMouseEnter" @onmouseleave="@this.OnMouseLeave">
         <MudPaper Height="20em" Outlined="true" Class="@this.dragClass" Style="overflow-y: auto;">
-            @foreach (var filePath in this.DocumentPaths)
+            @foreach (var fileAttachment in this.DocumentPaths)
             {
-                <MudChip T="string" Color="Color.Dark" Text="@Path.GetFileName(filePath)" tabindex="-1" Icon="@Icons.Material.Filled.Search" OnClick="@(() => this.InvestigateFile(filePath))" OnClose="@(() => this.RemoveDocument(filePath))"/>
+                <MudChip T="string" Color="Color.Dark" Text="@fileAttachment.FileName" tabindex="-1" Icon="@Icons.Material.Filled.Search" OnClick="@(() => this.InvestigateFile(fileAttachment))" OnClose="@(() => this.RemoveDocument(fileAttachment))"/>
             }
         </MudPaper>
     </div>
diff --git a/app/MindWork AI Studio/Components/AttachDocuments.razor.cs b/app/MindWork AI Studio/Components/AttachDocuments.razor.cs
index 942ce861..a647876e 100644
--- a/app/MindWork AI Studio/Components/AttachDocuments.razor.cs	
+++ b/app/MindWork AI Studio/Components/AttachDocuments.razor.cs	
@@ -1,3 +1,4 @@
+using AIStudio.Chat;
 using AIStudio.Dialogs;
 using AIStudio.Tools.PluginSystem;
 using AIStudio.Tools.Rust;
@@ -16,15 +17,15 @@ public partial class AttachDocuments : MSGComponentBase
     
     [Parameter]
     public string Name { get; set; } = string.Empty;
-    
+
     [Parameter]
-    public HashSet<string> DocumentPaths { get; set; } = [];
-    
+    public HashSet<FileAttachment> DocumentPaths { get; set; } = [];
+
     [Parameter]
-    public EventCallback<HashSet<string>> DocumentPathsChanged { get; set; }
-    
+    public EventCallback<HashSet<FileAttachment>> DocumentPathsChanged { get; set; }
+
     [Parameter]
-    public Func<HashSet<string>, Task> OnChange { get; set; } = _ => Task.CompletedTask;
+    public Func<HashSet<FileAttachment>, Task> OnChange { get; set; } = _ => Task.CompletedTask;
     
     /// <summary>
     /// Catch all documents that are hovered over the AI Studio window and not only over the drop zone. 
@@ -116,7 +117,7 @@ public partial class AttachDocuments : MSGComponentBase
                     if(!await FileExtensionValidation.IsExtensionValidWithNotifyAsync(path))
                         continue;
 
-                    this.DocumentPaths.Add(path);
+                    this.DocumentPaths.Add(FileAttachment.FromPath(path));
                 }
 
                 await this.DocumentPathsChanged.InvokeAsync(this.DocumentPaths);
@@ -160,7 +161,7 @@ public partial class AttachDocuments : MSGComponentBase
             if (!await FileExtensionValidation.IsExtensionValidWithNotifyAsync(selectedFilePath))
                 continue;
 
-            this.DocumentPaths.Add(selectedFilePath);
+            this.DocumentPaths.Add(FileAttachment.FromPath(selectedFilePath));
         }
         
         await this.DocumentPathsChanged.InvokeAsync(this.DocumentPaths);
@@ -199,23 +200,23 @@ public partial class AttachDocuments : MSGComponentBase
         this.StateHasChanged();
     }
 
-    private async Task RemoveDocument(string filePath)
+    private async Task RemoveDocument(FileAttachment fileAttachment)
     {
-        this.DocumentPaths.Remove(filePath);
-        
+        this.DocumentPaths.Remove(fileAttachment);
+
         await this.DocumentPathsChanged.InvokeAsync(this.DocumentPaths);
         await this.OnChange(this.DocumentPaths);
     }
 
     /// <summary>
-    /// The user might want to check what we actually extract from his file and therefore give the LLM as an input. 
+    /// The user might want to check what we actually extract from his file and therefore give the LLM as an input.
     /// </summary>
-    /// <param name="filePath">The file to check.</param>
-    private async Task InvestigateFile(string filePath)
+    /// <param name="fileAttachment">The file to check.</param>
+    private async Task InvestigateFile(FileAttachment fileAttachment)
     {
         var dialogParameters = new DialogParameters<DocumentCheckDialog>
         {
-            { x => x.FilePath, filePath },
+            { x => x.FilePath, fileAttachment.FilePath },
         };
 
         await this.DialogService.ShowAsync<DocumentCheckDialog>(T("Document Preview"), dialogParameters, DialogOptions.FULLSCREEN);
diff --git a/app/MindWork AI Studio/Components/ChatComponent.razor.cs b/app/MindWork AI Studio/Components/ChatComponent.razor.cs
index 2562c7b4..44b3dafa 100644
--- a/app/MindWork AI Studio/Components/ChatComponent.razor.cs	
+++ b/app/MindWork AI Studio/Components/ChatComponent.razor.cs	
@@ -57,7 +57,7 @@ public partial class ChatComponent : MSGComponentBase, IAsyncDisposable
     private string currentWorkspaceName = string.Empty;
     private Guid currentWorkspaceId = Guid.Empty;
     private CancellationTokenSource? cancellationTokenSource;
-    private HashSet<string> chatDocumentPaths = [];
+    private HashSet<FileAttachment> chatDocumentPaths = [];
 
     // Unfortunately, we need the input field reference to blur the focus away. Without
     // this, we cannot clear the input field.
@@ -464,7 +464,7 @@ public partial class ChatComponent : MSGComponentBase, IAsyncDisposable
             lastUserPrompt = new ContentText
             {
                 Text = this.userInput,
-                FileAttachments = this.chatDocumentPaths.ToList(),
+                FileAttachments = [..this.chatDocumentPaths],
             };
 
             //