diff --git a/apps/desktop/src/pages/ConversationPage.tsx b/apps/desktop/src/pages/ConversationPage.tsx
index d3a00bb..ade950d 100644
--- a/apps/desktop/src/pages/ConversationPage.tsx
+++ b/apps/desktop/src/pages/ConversationPage.tsx
@@ -16,6 +16,7 @@ import {
   ChevronDownIcon,
   ChevronUpIcon,
   EyeOffIcon,
+  PencilIcon,
   PlusIcon,
   PollIcon,
   ReplyIcon,
@@ -25,6 +26,7 @@ import {
   SpinnerIcon,
   XIcon,
 } from '../components/icons';
+import { ImageAnnotator } from '../components/ImageAnnotator';
 import { InCallPanel } from '../components/InCallPanel';
 import { IncomingCallPanel } from '../components/IncomingCallPanel';
 import { CallPreviewPanel } from '../components/CallPreviewPanel';
@@ -154,6 +156,7 @@ export function ConversationPage() {
   const [sendError, setSendError] = useState<string | null>(null);
   const [stickToBottom, setStickToBottom] = useState(true);
   const [attachments, setAttachments] = useState<File[]>([]);
+  const [annotatingIndex, setAnnotatingIndex] = useState<number | null>(null);
   const [infoPanelOpen, setInfoPanelOpen] = useState(false);
   const [mediaDrawerOpen, setMediaDrawerOpen] = useState(false);
   const [pollDialogOpen, setPollDialogOpen] = useState(false);
@@ -917,6 +920,9 @@ export function ConversationPage() {
                 key={idx}
                 file={file}
                 onRemove={() => setAttachments((prev) => prev.filter((_, i) => i !== idx))}
+                {...(file.type.startsWith('image/')
+                  ? { onEdit: () => setAnnotatingIndex(idx) }
+                  : {})}
               />
             ))}
           </div>
@@ -1163,6 +1169,17 @@ export function ConversationPage() {
         }}
         onUnpin={(messageId) => void handleTogglePin(messageId)}
       />
+
+      {annotatingIndex !== null && attachments[annotatingIndex] && (
+        <ImageAnnotator
+          file={attachments[annotatingIndex]!}
+          onCancel={() => setAnnotatingIndex(null)}
+          onSave={(next) => {
+            setAttachments((prev) => prev.map((f, i) => (i === annotatingIndex ? next : f)));
+            setAnnotatingIndex(null);
+          }}
+        />
+      )}
     </div>
   );
 }
@@ -1390,7 +1407,15 @@ function Banner({ children }: { children: React.ReactNode }) {
   );
 }
 
-function AttachmentPreview({ file, onRemove }: { file: File; onRemove: () => void }) {
+function AttachmentPreview({
+  file,
+  onRemove,
+  onEdit,
+}: {
+  file: File;
+  onRemove: () => void;
+  onEdit?: () => void;
+}) {
   const isImage = file.type.startsWith('image/');
   const [url, setUrl] = useState<string | null>(null);
   useEffect(() => {
@@ -1400,7 +1425,7 @@ function AttachmentPreview({ file, onRemove }: { file: File; onRemove: () => voi
     return () => URL.revokeObjectURL(u);
   }, [file, isImage]);
   return (
-    <div className="relative overflow-hidden rounded-lg border border-line bg-surface-2 dark:bg-[#2b2d31]">
+    <div className="group relative overflow-hidden rounded-lg border border-line bg-surface-2 dark:bg-[#2b2d31]">
       {isImage && url ? (
         <img src={url} alt={file.name} className="block h-20 w-20 object-cover" />
       ) : (
@@ -1412,6 +1437,17 @@ function AttachmentPreview({ file, onRemove }: { file: File; onRemove: () => voi
           <span className="text-fg-muted">{(file.size / 1024).toFixed(0)} KB</span>
         </div>
       )}
+      {isImage && onEdit && (
+        <button
+          type="button"
+          onClick={onEdit}
+          aria-label="Bearbeiten"
+          title="Bearbeiten"
+          className="absolute bottom-1 left-1 flex h-5 w-5 cursor-pointer items-center justify-center rounded-full bg-black/70 text-white opacity-0 transition group-hover:opacity-100 hover:bg-accent/80"
+        >
+          <PencilIcon className="h-3 w-3" />
+        </button>
+      )}
       <button
         type="button"
         onClick={onRemove}