diff --git a/pkg/clipboard/service.go b/pkg/clipboard/service.go
index f084990e..0e4332fa 100644
--- a/pkg/clipboard/service.go
+++ b/pkg/clipboard/service.go
@@ -3,6 +3,7 @@ package clipboard
 
 import (
 	"context"
+	"encoding/base64"
 
 	core "dappco.re/go/core"
 )
@@ -36,7 +37,7 @@ func (s *Service) OnStartup(_ context.Context) core.Result {
 		if !ok {
 			return core.Result{Value: false, OK: true}
 		}
-		data, _ := opts.Get("data").Value.([]byte)
+		data := clipboardImageData(opts)
 		if len(data) == 0 || len(data) > MaxImageBytes {
 			return core.Result{Value: false, OK: true}
 		}
@@ -92,3 +93,20 @@ func (s *Service) handleQuery(_ *core.Core, q core.Query) core.Result {
 		return core.Result{}
 	}
 }
+
+// clipboardImageData normalizes clipboard image inputs from MCP, preload bridge, and WS callers.
+// Use: bytes := clipboardImageData(core.NewOptions(core.Option{Key: "data", Value: "iVBORw0KGgo..."}))
+func clipboardImageData(opts core.Options) []byte {
+	if raw, ok := opts.Get("data").Value.([]byte); ok && len(raw) > 0 {
+		return append([]byte(nil), raw...)
+	}
+	encoded := opts.String("data")
+	if encoded == "" {
+		return nil
+	}
+	data, err := base64.StdEncoding.DecodeString(encoded)
+	if err != nil {
+		return nil
+	}
+	return data
+}
diff --git a/pkg/display/display.go b/pkg/display/display.go
index b45cd2c2..5aeb0620 100644
--- a/pkg/display/display.go
+++ b/pkg/display/display.go
@@ -545,6 +545,8 @@ func (s *Service) handleWSMessage(msg WSMessage) core.Result {
 		return c.Action("gui.chat.conversations.export").Run(ctx, wsOptions(msg.Data))
 	case "chat:attach-image":
 		return c.Action("gui.chat.attachImage").Run(ctx, wsOptions(msg.Data))
+	case "chat:attach-image-file":
+		return c.Action("gui.chat.attachImageFile").Run(ctx, wsOptions(msg.Data))
 	case "chat:remove-image":
 		return c.Action("gui.chat.removeImage").Run(ctx, wsOptions(msg.Data))
 	case "chat:thinking:start":
diff --git a/ui/src/chat/chat-state.service.ts b/ui/src/chat/chat-state.service.ts
index def9df56..fa84ec48 100644
--- a/ui/src/chat/chat-state.service.ts
+++ b/ui/src/chat/chat-state.service.ts
@@ -188,10 +188,13 @@ export class ChatStateService {
         continue;
       }
       const attachment = await this.fileToAttachment(file);
-      await this.invoke('gui.chat.attachImage', {
+      const queued = await this.invoke('gui.chat.attachImage', {
         conversation_id: this.activeConversation()?.id,
         ...attachment,
       });
+      if (queued) {
+        this.upsertQueuedAttachment(queued);
+      }
     }
   }
 
@@ -214,10 +217,13 @@ export class ChatStateService {
       return;
     }
     for (const path of paths) {
-      await this.invokeGUI<ImageAttachment>('gui.chat.attachImageFile', {
+      const attachment = await this.invoke('gui.chat.attachImageFile', {
         conversation_id: this.activeConversation()?.id,
         path,
       });
+      if (attachment) {
+        this.upsertQueuedAttachment(attachment);
+      }
     }
   }
 
@@ -398,7 +404,7 @@ export class ChatStateService {
       if (!data.attachment || conversationID !== activeID && !(conversationID === 'draft' && !this.activeConversation()?.messages.length)) {
         return;
       }
-      this.queuedAttachments.update((items) => [...items, data.attachment!]);
+      this.upsertQueuedAttachment(data.attachment);
     });
   }
 
@@ -480,6 +486,23 @@ export class ChatStateService {
     return model?.supports_vision ?? false;
   }
 
+  private upsertQueuedAttachment(attachment: ImageAttachment): void {
+    this.queuedAttachments.update((items) => {
+      if (items.some((item) => this.sameAttachment(item, attachment))) {
+        return items;
+      }
+      return [...items, attachment];
+    });
+  }
+
+  private sameAttachment(left: ImageAttachment, right: ImageAttachment): boolean {
+    return left.filename === right.filename &&
+      left.mime_type === right.mime_type &&
+      left.data === right.data &&
+      left.width === right.width &&
+      left.height === right.height;
+  }
+
   private async fileToAttachment(file: File): Promise<ImageAttachment> {
     const data = await this.readFileAsDataURL(file);
     const dimensions = await this.readImageDimensions(data);
diff --git a/ui/src/generated/core-gui-chat.bindings.ts b/ui/src/generated/core-gui-chat.bindings.ts
index 3e9d6d67..725a9ecf 100644
--- a/ui/src/generated/core-gui-chat.bindings.ts
+++ b/ui/src/generated/core-gui-chat.bindings.ts
@@ -42,6 +42,10 @@ export interface ChatRouteMap {
     request: ({ conversation_id?: string } & ImageAttachment);
     response: ImageAttachment;
   };
+  'gui.chat.attachImageFile': {
+    request: { conversation_id?: string; path: string };
+    response: ImageAttachment;
+  };
   'gui.chat.removeImage': {
     request: { conversation_id?: string; index: number };
     response: ImageAttachment;