diff --git a/app/MindWork AI Studio/Assistants/DocumentAnalysis/DocumentAnalysisAssistant.razor b/app/MindWork AI Studio/Assistants/DocumentAnalysis/DocumentAnalysisAssistant.razor
index 4b68618a..ec801e84 100644
--- a/app/MindWork AI Studio/Assistants/DocumentAnalysis/DocumentAnalysisAssistant.razor	
+++ b/app/MindWork AI Studio/Assistants/DocumentAnalysis/DocumentAnalysisAssistant.razor	
@@ -103,7 +103,7 @@ else
             @T("Documents for the analysis")
         </MudText>
         
-        <AttachDocuments Name="Document Analysis Files" @bind-DocumentPaths="@this.loadedDocumentPaths" CatchAllDocuments="true" UseSmallForm="false"/>
+        <AttachDocuments Name="Document Analysis Files" @bind-DocumentPaths="@this.loadedDocumentPaths" CatchAllDocuments="true" UseSmallForm="false" Provider="@this.providerSettings"/>
         
     </ExpansionPanel>
 </MudExpansionPanels>
diff --git a/app/MindWork AI Studio/Components/AttachDocuments.razor.cs b/app/MindWork AI Studio/Components/AttachDocuments.razor.cs
index a647876e..bddcbe43 100644
--- a/app/MindWork AI Studio/Components/AttachDocuments.razor.cs	
+++ b/app/MindWork AI Studio/Components/AttachDocuments.razor.cs	
@@ -36,6 +36,9 @@ public partial class AttachDocuments : MSGComponentBase
     [Parameter]
     public bool UseSmallForm { get; set; }
     
+    [Parameter]
+    public AIStudio.Settings.Provider? Provider { get; set; }
+    
     [Inject]
     private ILogger<AttachDocuments> Logger { get; set; } = null!;
     
@@ -114,7 +117,7 @@ public partial class AttachDocuments : MSGComponentBase
 
                 foreach (var path in paths)
                 {
-                    if(!await FileExtensionValidation.IsExtensionValidWithNotifyAsync(path))
+                    if(!await FileExtensionValidation.IsExtensionValidWithNotifyAsync(FileExtensionValidation.UseCase.ATTACHING_CONTENT, path, this.Provider))
                         continue;
 
                     this.DocumentPaths.Add(FileAttachment.FromPath(path));
@@ -158,7 +161,7 @@ public partial class AttachDocuments : MSGComponentBase
             if (!File.Exists(selectedFilePath))
                 continue;
 
-            if (!await FileExtensionValidation.IsExtensionValidWithNotifyAsync(selectedFilePath))
+            if (!await FileExtensionValidation.IsExtensionValidWithNotifyAsync(FileExtensionValidation.UseCase.ATTACHING_CONTENT, selectedFilePath, this.Provider))
                 continue;
 
             this.DocumentPaths.Add(FileAttachment.FromPath(selectedFilePath));
diff --git a/app/MindWork AI Studio/Components/ChatComponent.razor b/app/MindWork AI Studio/Components/ChatComponent.razor
index 8f4eca23..1eb28244 100644
--- a/app/MindWork AI Studio/Components/ChatComponent.razor	
+++ b/app/MindWork AI Studio/Components/ChatComponent.razor	
@@ -83,7 +83,7 @@
             
             <ChatTemplateSelection CanChatThreadBeUsedForTemplate="@this.CanThreadBeSaved" CurrentChatThread="@this.ChatThread" CurrentChatTemplate="@this.currentChatTemplate" CurrentChatTemplateChanged="@this.ChatTemplateWasChanged"/>
 
-            <AttachDocuments Name="File Attachments" @bind-DocumentPaths="@this.chatDocumentPaths" CatchAllDocuments="true" UseSmallForm="true"/>
+            <AttachDocuments Name="File Attachments" @bind-DocumentPaths="@this.chatDocumentPaths" CatchAllDocuments="true" UseSmallForm="true" Provider="@this.Provider"/>
 
             @if (this.SettingsManager.ConfigurationData.Workspace.StorageBehavior is WorkspaceStorageBehavior.STORE_CHATS_AUTOMATICALLY)
             {
diff --git a/app/MindWork AI Studio/Components/ReadFileContent.razor.cs b/app/MindWork AI Studio/Components/ReadFileContent.razor.cs
index cd970cd4..5db85e21 100644
--- a/app/MindWork AI Studio/Components/ReadFileContent.razor.cs	
+++ b/app/MindWork AI Studio/Components/ReadFileContent.razor.cs	
@@ -55,7 +55,7 @@ public partial class ReadFileContent : MSGComponentBase
             return;
         }
 
-        if (!await FileExtensionValidation.IsExtensionValidWithNotifyAsync(selectedFile.SelectedFilePath))
+        if (!await FileExtensionValidation.IsExtensionValidWithNotifyAsync(FileExtensionValidation.UseCase.DIRECTLY_LOADING_CONTENT, selectedFile.SelectedFilePath))
         {
             this.Logger.LogWarning("User attempted to load unsupported file: {FilePath}", selectedFile.SelectedFilePath);
             return;
diff --git a/app/MindWork AI Studio/Tools/Validation/FileExtensionValidation.cs b/app/MindWork AI Studio/Tools/Validation/FileExtensionValidation.cs
index 8be34eca..991dcbdf 100644
--- a/app/MindWork AI Studio/Tools/Validation/FileExtensionValidation.cs	
+++ b/app/MindWork AI Studio/Tools/Validation/FileExtensionValidation.cs	
@@ -1,3 +1,5 @@
+using AIStudio.Provider;
+using AIStudio.Settings;
 using AIStudio.Tools.PluginSystem;
 using AIStudio.Tools.Rust;
 
@@ -10,12 +12,35 @@ public static class FileExtensionValidation
 {
     private static string TB(string fallbackEN) => I18N.I.T(fallbackEN, typeof(FileExtensionValidation).Namespace, nameof(FileExtensionValidation));
 
+    /// <summary>
+    /// Defines the use cases for file extension validation.
+    /// </summary>
+    public enum UseCase
+    {
+        /// <summary>
+        /// No specific use case; general validation.
+        /// </summary>
+        NONE,
+        
+        /// <summary>
+        /// Validating for directly loading content into the UI. In this state, there might be no provider selected yet.
+        /// </summary>
+        DIRECTLY_LOADING_CONTENT,
+        
+        /// <summary>
+        /// Validating for attaching content to a message or prompt.
+        /// </summary>
+        ATTACHING_CONTENT,
+    }
+    
     /// <summary>
     /// Validates the file extension and sends appropriate MessageBus notifications when invalid.
     /// </summary>
+    /// <param name="useCae">The validation use case.</param>
     /// <param name="filePath">The file path to validate.</param>
+    /// <param name="provider">The selected provider.</param>
     /// <returns>True if valid, false if invalid (error/warning already sent via MessageBus).</returns>
-    public static async Task<bool> IsExtensionValidWithNotifyAsync(string filePath)
+    public static async Task<bool> IsExtensionValidWithNotifyAsync(UseCase useCae, string filePath, Settings.Provider? provider = null)
     {
         var ext = Path.GetExtension(filePath).TrimStart('.').ToLowerInvariant();
         if(FileTypeFilter.Executables.FilterExtensions.Contains(ext))
@@ -26,12 +51,36 @@ public static class FileExtensionValidation
             return false;
         }
 
-        if(FileTypeFilter.AllImages.FilterExtensions.Contains(ext))
+        var capabilities = provider?.GetModelCapabilities() ?? new();
+        if (FileTypeFilter.AllImages.FilterExtensions.Contains(ext))
         {
-            await MessageBus.INSTANCE.SendWarning(new(
-                Icons.Material.Filled.ImageNotSupported,
-                TB("Images are not supported yet")));
-            return false;
+            switch (useCae)
+            {
+                // In this use case, we cannot guarantee that a provider is selected yet:
+                case UseCase.DIRECTLY_LOADING_CONTENT:
+                    await MessageBus.INSTANCE.SendWarning(new(
+                        Icons.Material.Filled.ImageNotSupported,
+                        TB("Images are not supported at this place")));
+                    return false;
+                
+                // In this use case, we can check the provider capabilities:
+                case UseCase.ATTACHING_CONTENT when capabilities.Contains(Capability.SINGLE_IMAGE_INPUT) ||
+                                                    capabilities.Contains(Capability.MULTIPLE_IMAGE_INPUT):
+                    return true;
+                
+                // We know that images are not supported:
+                case UseCase.ATTACHING_CONTENT:
+                    await MessageBus.INSTANCE.SendWarning(new(
+                        Icons.Material.Filled.ImageNotSupported,
+                        TB("Images are not supported by the selected provider and model")));
+                    return false;
+                
+                default:
+                    await MessageBus.INSTANCE.SendWarning(new(
+                        Icons.Material.Filled.ImageNotSupported,
+                        TB("Images are not supported yet")));
+                    return false;
+            }
         }
 
         if(FileTypeFilter.AllVideos.FilterExtensions.Contains(ext))