diff --git a/apps/app/components/tiptap/extensions/updated-image.tsx b/apps/app/components/tiptap/extensions/updated-image.tsx
index b24ff2cc8..01648dcd7 100644
--- a/apps/app/components/tiptap/extensions/updated-image.tsx
+++ b/apps/app/components/tiptap/extensions/updated-image.tsx
@@ -1,9 +1,10 @@
 import Image from "@tiptap/extension-image";
+import TrackImageDeletionPlugin from "../plugins/delete-image";
 import UploadImagesPlugin from "../plugins/upload-image";
 
 const UpdatedImage = Image.extend({
   addProseMirrorPlugins() {
-    return [UploadImagesPlugin()];
+    return [UploadImagesPlugin(), TrackImageDeletionPlugin()];
   },
   addAttributes() {
     return {
diff --git a/apps/app/components/tiptap/index.tsx b/apps/app/components/tiptap/index.tsx
index 3f1c3be0e..a96b9c971 100644
--- a/apps/app/components/tiptap/index.tsx
+++ b/apps/app/components/tiptap/index.tsx
@@ -1,14 +1,9 @@
-// @ts-nocheck
 import { useEditor, EditorContent, Editor } from "@tiptap/react";
 import { useDebouncedCallback } from "use-debounce";
 import { EditorBubbleMenu } from "./bubble-menu";
 import { TiptapExtensions } from "./extensions";
 import { TiptapEditorProps } from "./props";
-import { Node } from "@tiptap/pm/model";
-import { Editor as CoreEditor } from "@tiptap/core";
-import { useCallback, useImperativeHandle, useRef } from "react";
-import { EditorState } from "@tiptap/pm/state";
-import fileService from "services/file.service";
+import { useImperativeHandle, useRef } from "react";
 import { ImageResizer } from "./extensions/image-resize";
 
 export interface ITiptapRichTextEditor {
@@ -51,7 +46,6 @@ const Tiptap = (props: ITiptapRichTextEditor) => {
       // for instant feedback loop
       setIsSubmitting?.("submitting");
       setShouldShowAlert?.(true);
-      checkForNodeDeletions(editor);
       if (debouncedUpdatesEnabled) {
         debouncedUpdates({ onChange, editor });
       } else {
@@ -71,45 +65,6 @@ const Tiptap = (props: ITiptapRichTextEditor) => {
     },
   }));
 
-  const previousState = useRef<EditorState>();
-
-  const onNodeDeleted = useCallback(async (node: Node) => {
-    if (node.type.name === "image") {
-      const assetUrlWithWorkspaceId = new URL(node.attrs.src).pathname.substring(1);
-      const resStatus = await fileService.deleteImage(assetUrlWithWorkspaceId);
-      if (resStatus === 204) {
-        console.log("file deleted successfully");
-      }
-    }
-  }, []);
-
-  const checkForNodeDeletions = useCallback(
-    (editor: CoreEditor) => {
-      const prevNodesById: Record<string, Node> = {};
-      previousState.current?.doc.forEach((node) => {
-        if (node.attrs.id) {
-          prevNodesById[node.attrs.id] = node;
-        }
-      });
-
-      const nodesById: Record<string, Node> = {};
-      editor.state?.doc.forEach((node) => {
-        if (node.attrs.id) {
-          nodesById[node.attrs.id] = node;
-        }
-      });
-
-      previousState.current = editor.state;
-
-      for (const [id, node] of Object.entries(prevNodesById)) {
-        if (nodesById[id] === undefined) {
-          onNodeDeleted(node);
-        }
-      }
-    },
-    [onNodeDeleted]
-  );
-
   const debouncedUpdates = useDebouncedCallback(async ({ onChange, editor }) => {
     setTimeout(async () => {
       if (onChange) {
diff --git a/apps/app/components/tiptap/plugins/delete-image.tsx b/apps/app/components/tiptap/plugins/delete-image.tsx
new file mode 100644
index 000000000..df189ee3a
--- /dev/null
+++ b/apps/app/components/tiptap/plugins/delete-image.tsx
@@ -0,0 +1,57 @@
+import { Plugin, PluginKey } from "@tiptap/pm/state";
+import { Node as ProseMirrorNode } from '@tiptap/pm/model';
+import fileService from "services/file.service";
+
+const deleteKey = new PluginKey("delete-image");
+
+const TrackImageDeletionPlugin = () =>
+  new Plugin({
+    key: deleteKey,
+    appendTransaction: (transactions, oldState, newState) => {
+      transactions.forEach((transaction) => {
+        if (!transaction.docChanged) return;
+
+        const removedImages: ProseMirrorNode[] = [];
+
+        oldState.doc.descendants((oldNode, oldPos) => {
+          console.log(oldNode.type.name)
+          if (oldNode.type.name !== 'image') return;
+
+          if (!newState.doc.resolve(oldPos).parent) return;
+          const newNode = newState.doc.nodeAt(oldPos);
+
+          // Check if the node has been deleted or replaced
+          if (!newNode || newNode.type.name !== 'image') {
+            // Check if the node still exists elsewhere in the document
+            let nodeExists = false;
+            newState.doc.descendants((node) => {
+              if (node.attrs.id === oldNode.attrs.id) {
+                nodeExists = true;
+              }
+            });
+
+            if (!nodeExists) {
+              removedImages.push(oldNode as ProseMirrorNode);
+            }
+          }
+        });
+
+        removedImages.forEach((node) => {
+          const src = node.attrs.src;
+          onNodeDeleted(src);
+        });
+      });
+
+      return null;
+    },
+  });
+
+export default TrackImageDeletionPlugin;
+
+async function onNodeDeleted(src: string) {
+  const assetUrlWithWorkspaceId = new URL(src).pathname.substring(1);
+  const resStatus = await fileService.deleteImage(assetUrlWithWorkspaceId);
+  if (resStatus === 204) {
+    console.log("Image deleted successfully");
+  }
+}
diff --git a/apps/app/components/tiptap/plugins/upload-image.tsx b/apps/app/components/tiptap/plugins/upload-image.tsx
index 32cdd6731..5897e9ffb 100644
--- a/apps/app/components/tiptap/plugins/upload-image.tsx
+++ b/apps/app/components/tiptap/plugins/upload-image.tsx
@@ -24,7 +24,7 @@ const UploadImagesPlugin = () =>
           const image = document.createElement("img");
           image.setAttribute(
             "class",
-            "w-[35%] opacity-10 rounded-lg border border-custom-border-300",
+            "opacity-10 rounded-lg border border-custom-border-300",
           );
           image.src = src;
           placeholder.appendChild(image);
diff --git a/apps/app/styles/editor.css b/apps/app/styles/editor.css
index 05817c0dc..65e947eeb 100644
--- a/apps/app/styles/editor.css
+++ b/apps/app/styles/editor.css
@@ -126,3 +126,27 @@ ul[data-type="taskList"] li[data-checked="true"] > div > p {
   transition: opacity 0.2s ease-out;
 }
 
+.img-placeholder {
+  position: relative;
+  width: 35%;
+
+  &:before {
+    content: "";
+    box-sizing: border-box;
+    position: absolute;
+    top: 50%;
+    left: 50%;
+    width: 20px;
+    height: 20px;
+    border-radius: 50%;
+    border: 3px solid rgba(var(--color-text-200));
+    border-top-color: rgba(var(--color-text-800)); 
+    animation: spinning 0.6s linear infinite;
+  }
+}
+
+@keyframes spinning {
+  to {
+    transform: rotate(360deg);
+  }
+}