diff --git a/plugins/ckeditor5-woltlab-image/src/woltlabimage.ts b/plugins/ckeditor5-woltlab-image/src/woltlabimage.ts
index b61aef7..8f800f5 100644
--- a/plugins/ckeditor5-woltlab-image/src/woltlabimage.ts
+++ b/plugins/ckeditor5-woltlab-image/src/woltlabimage.ts
@@ -11,7 +11,7 @@
  * @since 6.0
  */
 
-import { Plugin } from "@ckeditor/ckeditor5-core";
+import { Command, Plugin } from "@ckeditor/ckeditor5-core";
 import type {
   DocumentSelection,
   DowncastAttributeEvent,
@@ -22,6 +22,7 @@ import type {
   Selection,
 } from "@ckeditor/ckeditor5-engine";
 import { ImageUtils } from "@ckeditor/ckeditor5-image";
+import { ObservableSetEvent } from "@ckeditor/ckeditor5-utils";
 
 export class WoltlabImage extends Plugin {
   static get pluginName() {
@@ -33,6 +34,10 @@ export class WoltlabImage extends Plugin {
   }
 
   init() {
+    this.#decorateCommand(this.editor.commands.get("uploadImage")!);
+    this.#decorateCommand(this.editor.commands.get("insertImage")!);
+    this.#decorateCommand(this.editor.commands.get("replaceImageSource")!);
+
     const { conversion } = this.editor;
 
     const imageTypes = ["imageBlock", "imageInline"] as const;
@@ -149,6 +154,39 @@ export class WoltlabImage extends Plugin {
       imageUtils.findViewImgElement(viewElement)!,
     );
   }
+
+  #decorateCommand(command: Command) {
+    const imageUtils: ImageUtils = this.editor.plugins.get("ImageUtils");
+    command.on<ObservableSetEvent<boolean>>(
+      "set:isEnabled",
+      (evt, _, value) => {
+        if (!value) {
+          return;
+        }
+        const selection = this.editor.model.document.selection;
+        const element = imageUtils.getClosestSelectedImageElement(selection);
+        if (!element) {
+          return;
+        }
+        evt.return = !(this.#isAttachment(element) || this.#isMedia(element));
+      },
+      { priority: "high" },
+    );
+  }
+
+  #isAttachment(element: Element): boolean {
+    return (
+      element.getAttribute("classList") === "woltlabAttachment" ||
+      element.hasAttribute("attachmentId")
+    );
+  }
+
+  #isMedia(element: Element): boolean {
+    return (
+      element.getAttribute("classList") === "woltlabSuiteMedia" ||
+      element.hasAttribute("mediaId")
+    );
+  }
 }
 
 export default WoltlabImage;