diff --git a/apps/client/src/features/editor/components/attachment/attachment-view.tsx b/apps/client/src/features/editor/components/attachment/attachment-view.tsx
index d38585202..48ab6cd69 100644
--- a/apps/client/src/features/editor/components/attachment/attachment-view.tsx
+++ b/apps/client/src/features/editor/components/attachment/attachment-view.tsx
@@ -1,5 +1,5 @@
 import { NodeViewProps, NodeViewWrapper } from "@tiptap/react";
-import { Group, Text, Paper, ActionIcon } from "@mantine/core";
+import { Group, Text, Paper, ActionIcon, Loader } from "@mantine/core";
 import { getFileUrl } from "@/lib/config.ts";
 import { IconDownload, IconPaperclip } from "@tabler/icons-react";
 import { useHover } from "@mantine/hooks";
@@ -21,10 +21,10 @@ export default function AttachmentView(props: NodeViewProps) {
           h={25}
         >
           <Group justify="space-between" wrap="nowrap">
-            <IconPaperclip size={20} />
+            {url ? <IconPaperclip size={20} /> : <Loader size={20} />}
 
             <Text component="span" size="md" truncate="end">
-              {name}
+              {url ? name : `Uploading ${name}...`}
             </Text>
 
             <Text component="span" size="sm" c="dimmed" inline>
@@ -32,14 +32,12 @@ export default function AttachmentView(props: NodeViewProps) {
             </Text>
           </Group>
 
-          {selected || hovered ? (
+          {url && (selected || hovered) && (
             <a href={getFileUrl(url)} target="_blank">
               <ActionIcon variant="default" aria-label="download file">
                 <IconDownload size={18} />
               </ActionIcon>
             </a>
-          ) : (
-            ""
           )}
         </Group>
       </Paper>
diff --git a/apps/client/src/features/editor/components/slash-menu/menu-items.ts b/apps/client/src/features/editor/components/slash-menu/menu-items.ts
index 11a889255..e3bf5622e 100644
--- a/apps/client/src/features/editor/components/slash-menu/menu-items.ts
+++ b/apps/client/src/features/editor/components/slash-menu/menu-items.ts
@@ -237,6 +237,9 @@ const CommandGroups: SlashMenuGroupedItemsType = {
             const pos = editor.view.state.selection.from;
             uploadAttachmentAction(file, editor.view, pos, pageId, true);
           }
+
+          // Reset the input value to allow uploading the same file again if needed
+          input.value = "";
         };
         input.click();
       },
diff --git a/packages/editor-ext/src/lib/attachment/attachment-upload.ts b/packages/editor-ext/src/lib/attachment/attachment-upload.ts
index 0d2ac6c73..e50be56ed 100644
--- a/packages/editor-ext/src/lib/attachment/attachment-upload.ts
+++ b/packages/editor-ext/src/lib/attachment/attachment-upload.ts
@@ -1,126 +1,102 @@
-import { type EditorState, Plugin, PluginKey } from "@tiptap/pm/state";
-import { Decoration, DecorationSet } from "@tiptap/pm/view";
-import {
-  insertTrailingNode,
-  MediaUploadOptions,
-  UploadFn,
-} from "../media-utils";
+import { Node } from "@tiptap/pm/model";
+import { MediaUploadOptions, UploadFn } from "../media-utils";
 import { IAttachment } from "../types";
+import { generateNodeId } from "../utils";
 
-const uploadKey = new PluginKey("attachment-upload");
+const findAttachmentNodeByPlaceholderId = (
+  doc: Node,
+  placeholderId: string,
+): { node: Node; pos: number } | null => {
+  let result: { node: Node; pos: number } | null = null;
 
-export const AttachmentUploadPlugin = ({
-  placeholderClass,
-}: {
-  placeholderClass: string;
-}) =>
-  new Plugin({
-    key: uploadKey,
-    state: {
-      init() {
-        return DecorationSet.empty;
-      },
-      apply(tr, set) {
-        set = set.map(tr.mapping, tr.doc);
-        // See if the transaction adds or removes any placeholders
-        //@-ts-expect-error - not yet sure what the type I need here
-        const action = tr.getMeta(this);
-        if (action?.add) {
-          const { id, pos, fileName } = action.add;
-
-          const placeholder = document.createElement("div");
-          placeholder.setAttribute("class", placeholderClass);
-
-          const uploadingText = document.createElement("span");
-          uploadingText.setAttribute("class", "uploading-text");
-          uploadingText.textContent = `Uploading ${fileName}`;
-
-          placeholder.appendChild(uploadingText);
-
-          const realPos = pos + 1;
-          const deco = Decoration.widget(realPos, placeholder, {
-            id,
-          });
-          set = set.add(tr.doc, [deco]);
-        } else if (action?.remove) {
-          set = set.remove(
-            set.find(
-              undefined,
-              undefined,
-              (spec) => spec.id == action.remove.id,
-            ),
-          );
-        }
-        return set;
-      },
-    },
-    props: {
-      decorations(state) {
-        return this.getState(state);
-      },
-    },
+  doc.descendants((node, pos) => {
+    if (result) return false;
+    if (
+      node.type.name === "attachment" &&
+      node.attrs.placeholderId === placeholderId
+    ) {
+      result = { node, pos };
+      return false;
+    }
+    return true;
   });
 
-function findPlaceholder(state: EditorState, id: {}) {
-  const decos = uploadKey.getState(state) as DecorationSet;
-  const found = decos.find(undefined, undefined, (spec) => spec.id == id);
-  return found.length ? found[0]?.from : null;
-}
-
-export const handleAttachmentUpload =
+  return result;
+};
+const handleAttachmentUpload =
   ({ validateFn, onUpload }: MediaUploadOptions): UploadFn =>
   async (file, view, pos, pageId, allowMedia) => {
     const validated = validateFn?.(file, allowMedia);
     // @ts-ignore
     if (!validated) return;
-    // A fresh object to act as the ID for this upload
-    const id = {};
 
-    // Replace the selection with a placeholder
-    const tr = view.state.tr;
-    if (!tr.selection.empty) tr.deleteSelection();
-
-    tr.setMeta(uploadKey, {
-      add: {
-        id,
-        pos,
-        fileName: file.name,
-      },
+    const placeholderId = generateNodeId();
+    const initialPlaceholderNode = view.state.schema.nodes.attachment?.create({
+      placeholderId,
+      name: file.name,
+      size: file.size,
     });
 
-    insertTrailingNode(tr, pos, view);
-    view.dispatch(tr);
+    let placeholderShown = false;
+    let tr = view.state.tr;
 
-    await onUpload(file, pageId).then(
-      (attachment: IAttachment) => {
-        const { schema } = view.state;
+    if (!initialPlaceholderNode) return;
 
-        const pos = findPlaceholder(view.state, id);
+    const { parent } = tr.doc.resolve(pos);
+    const isEmptyTextBlock = parent.isTextblock && !parent.childCount;
 
-        if (pos == null) return;
+    if (isEmptyTextBlock) {
+      tr.replaceRangeWith(pos - 1, pos + 1, initialPlaceholderNode);
+    } else {
+      tr.insert(pos, initialPlaceholderNode);
+    }
 
-        if (!attachment) return;
+    // Only show the placeholder if the upload takes more than 250ms
+    const displayPlaceholderTimeout = setTimeout(() => {
+      view.dispatch(tr);
+      placeholderShown = true;
+      tr = view.state.tr;
+    }, 250);
 
-        const node = schema.nodes.attachment?.create({
-          url: `/api/files/${attachment.id}/${attachment.fileName}`,
-          name: attachment.fileName,
-          mime: attachment.mimeType,
-          size: attachment.fileSize,
-          attachmentId: attachment.id,
-        });
-        if (!node) return;
+    try {
+      const attachment: IAttachment = await onUpload(file, pageId);
+      const { pos: currentPos = null } =
+        findAttachmentNodeByPlaceholderId(tr.doc, placeholderId) || {};
 
-        const transaction = view.state.tr
-          .replaceWith(pos, pos, node)
-          .setMeta(uploadKey, { remove: { id } });
-        view.dispatch(transaction);
-      },
-      () => {
-        // Deletes the placeholder on error
-        const transaction = view.state.tr
-          .delete(pos, pos)
-          .setMeta(uploadKey, { remove: { id } });
-        view.dispatch(transaction);
-      },
-    );
+      //  If the placeholder is not found or attachment is missing, abort the process
+      if (currentPos === null || !attachment) return;
+
+      // Update the placeholder node with the actual attachment data
+      tr.setNodeMarkup(currentPos, undefined, {
+        url: `/api/files/${attachment.id}/${attachment.fileName}`,
+        name: attachment.fileName,
+        mime: attachment.mimeType,
+        size: attachment.fileSize,
+        attachmentId: attachment.id,
+      });
+    } catch (error) {
+      const { pos: currentPos = null } =
+        findAttachmentNodeByPlaceholderId(tr.doc, placeholderId) || {};
+
+      if (currentPos === null) return;
+
+      // Delete the placeholder on error
+      tr.delete(
+        currentPos,
+        currentPos + (initialPlaceholderNode.nodeSize ?? 1),
+      );
+    } finally {
+      clearTimeout(displayPlaceholderTimeout);
+
+      // If the placeholder was shown, delay showing the attachment to avoid flicker
+      if (placeholderShown) {
+        setTimeout(() => {
+          view.dispatch(tr);
+        }, 100);
+      } else {
+        view.dispatch(tr);
+      }
+    }
   };
+
+export { handleAttachmentUpload };
diff --git a/packages/editor-ext/src/lib/attachment/attachment.ts b/packages/editor-ext/src/lib/attachment/attachment.ts
index bd1814f5f..34a8fe42e 100644
--- a/packages/editor-ext/src/lib/attachment/attachment.ts
+++ b/packages/editor-ext/src/lib/attachment/attachment.ts
@@ -1,6 +1,5 @@
 import { Node, mergeAttributes } from "@tiptap/core";
 import { ReactNodeViewRenderer } from "@tiptap/react";
-import { AttachmentUploadPlugin } from "./attachment-upload";
 
 export interface AttachmentOptions {
   HTMLAttributes: Record<string, any>;
@@ -13,6 +12,7 @@ export interface AttachmentAttributes {
   mime?: string; // e.g. application/zip
   size?: number;
   attachmentId?: string;
+  placeholderId?: string;
 }
 
 declare module "@tiptap/core" {
@@ -75,6 +75,14 @@ export const Attachment = Node.create<AttachmentOptions>({
           "data-attachment-id": attributes.attachmentId,
         }),
       },
+      placeholderId: {
+        default: null,
+        parseHTML: (element) =>
+          element.getAttribute("data-attachment-placeholder-id"),
+        renderHTML: (attributes: AttachmentAttributes) => ({
+          "data-attachment-placeholder-id": attributes.placeholderId,
+        }),
+      },
     };
   },
 
@@ -92,7 +100,7 @@ export const Attachment = Node.create<AttachmentOptions>({
       mergeAttributes(
         { "data-type": this.name },
         this.options.HTMLAttributes,
-        HTMLAttributes
+        HTMLAttributes,
       ),
       [
         "a",
@@ -125,12 +133,4 @@ export const Attachment = Node.create<AttachmentOptions>({
 
     return ReactNodeViewRenderer(this.options.view);
   },
-
-  addProseMirrorPlugins() {
-    return [
-      AttachmentUploadPlugin({
-        placeholderClass: "attachment-placeholder",
-      }),
-    ];
-  },
 });