diff --git a/shared/editor/commands/insertFiles.ts b/shared/editor/commands/insertFiles.ts
index 4fa0bfc45..39e71dbc5 100644
--- a/shared/editor/commands/insertFiles.ts
+++ b/shared/editor/commands/insertFiles.ts
@@ -1,12 +1,10 @@
 import * as Sentry from "@sentry/react";
-import { NodeSelection } from "prosemirror-state";
 import { EditorView } from "prosemirror-view";
 import { v4 as uuidv4 } from "uuid";
 import FileHelper from "../lib/FileHelper";
 import uploadPlaceholderPlugin, {
   findPlaceholder,
 } from "../lib/uploadPlaceholder";
-import findAttachmentById from "../queries/findAttachmentById";
 
 export type Options = {
   /** Dictionary object containing translation strings */
@@ -61,7 +59,6 @@ const insertFiles = function (
 
   // we'll use this to track of how many files have succeeded or failed
   let complete = 0;
-  let attachmentPlaceholdersSet = false;
 
   const filesToUpload = files.map((file) => ({
     id: `upload-${uuidv4()}`,
@@ -76,55 +73,14 @@ const insertFiles = function (
   for (const upload of filesToUpload) {
     const { tr } = view.state;
 
-    if (upload.isImage) {
-      // insert a placeholder at this position, or mark an existing file as being
-      // replaced
-      tr.setMeta(uploadPlaceholderPlugin, {
-        add: {
-          id: upload.id,
-          file: upload.file,
-          pos,
-          isImage: true,
-          replaceExisting: options.replaceExisting,
-        },
-      });
-      view.dispatch(tr);
-    } else if (upload.isVideo) {
-      // insert a placeholder at this position, or mark an existing file as being
-      // replaced
-      tr.setMeta(uploadPlaceholderPlugin, {
-        add: {
-          id: upload.id,
-          file: upload.file,
-          pos,
-          isVideo: true,
-        },
-      });
-      view.dispatch(tr);
-    } else if (!attachmentPlaceholdersSet) {
-      // Skip if the editor does not support attachments.
-      if (!view.state.schema.nodes.attachment) {
-        continue;
-      }
-
-      const attachmentsToUpload = filesToUpload.filter(
-        (i) => i.isImage === false
-      );
-
-      view.dispatch(
-        tr.insert(
-          pos,
-          attachmentsToUpload.map((attachment) =>
-            schema.nodes.attachment.create({
-              id: attachment.id,
-              title: attachment.file.name ?? dictionary.untitled,
-              size: attachment.file.size,
-            })
-          )
-        )
-      );
-      attachmentPlaceholdersSet = true;
-    }
+    tr.setMeta(uploadPlaceholderPlugin, {
+      add: {
+        pos,
+        ...upload,
+        replaceExisting: options.replaceExisting,
+      },
+    });
+    view.dispatch(tr);
 
     // start uploading the file to the server. Using "then" syntax
     // to allow all placeholders to be entered at once with the uploads
@@ -135,9 +91,6 @@ const insertFiles = function (
           const newImg = new Image();
           newImg.onload = () => {
             const result = findPlaceholder(view.state, upload.id);
-
-            // if the content around the placeholder has been deleted
-            // then forget about inserting this file
             if (result === null) {
               return;
             }
@@ -152,17 +105,6 @@ const insertFiles = function (
                 )
                 .setMeta(uploadPlaceholderPlugin, { remove: { id: upload.id } })
             );
-
-            // If the users selection is still at the file then make sure to select
-            // the entire node once done. Otherwise, if the selection has moved
-            // elsewhere then we don't want to modify it
-            if (view.state.selection.from === from) {
-              view.dispatch(
-                view.state.tr.setSelection(
-                  new NodeSelection(view.state.doc.resolve(from))
-                )
-              );
-            }
           };
 
           newImg.onerror = () => {
@@ -172,9 +114,6 @@ const insertFiles = function (
           newImg.src = src;
         } else if (upload.isVideo) {
           const result = findPlaceholder(view.state, upload.id);
-
-          // if the content around the placeholder has been deleted
-          // then forget about inserting this file
           if (result === null) {
             return;
           }
@@ -197,71 +136,41 @@ const insertFiles = function (
               )
               .setMeta(uploadPlaceholderPlugin, { remove: { id: upload.id } })
           );
-
-          // If the users selection is still at the file then make sure to select
-          // the entire node once done. Otherwise, if the selection has moved
-          // elsewhere then we don't want to modify it
-          if (view.state.selection.from === from) {
-            view.dispatch(
-              view.state.tr.setSelection(
-                new NodeSelection(view.state.doc.resolve(from))
-              )
-            );
-          }
         } else {
-          const result = findAttachmentById(view.state, upload.id);
-
-          // if the attachment has been deleted then forget about updating it
+          const result = findPlaceholder(view.state, upload.id);
           if (result === null) {
             return;
           }
 
           const [from, to] = result;
-          view.dispatch(
-            view.state.tr.replaceWith(
-              from,
-              to || from,
-              schema.nodes.attachment.create({
-                href: src,
-                title: upload.file.name ?? dictionary.untitled,
-                size: upload.file.size,
-              })
-            )
-          );
 
-          // If the users selection is still at the file then make sure to select
-          // the entire node once done. Otherwise, if the selection has moved
-          // elsewhere then we don't want to modify it
-          if (view.state.selection.from === from) {
-            view.dispatch(
-              view.state.tr.setSelection(
-                new NodeSelection(view.state.doc.resolve(from))
+          view.dispatch(
+            view.state.tr
+              .replaceWith(
+                from,
+                to || from,
+                schema.nodes.attachment.create({
+                  href: src,
+                  title: upload.file.name ?? dictionary.untitled,
+                  size: upload.file.size,
+                })
               )
-            );
-          }
+              .setMeta(uploadPlaceholderPlugin, { remove: { id: upload.id } })
+          );
         }
       })
       .catch((error) => {
         Sentry.captureException(error);
 
+        // eslint-disable-next-line no-console
+        console.error(error);
+
         // cleanup the placeholder if there is a failure
-        if (upload.isImage || upload.isVideo) {
-          view.dispatch(
-            view.state.tr.setMeta(uploadPlaceholderPlugin, {
-              remove: { id: upload.id },
-            })
-          );
-        } else {
-          const result = findAttachmentById(view.state, upload.id);
-
-          // if the attachment has been deleted then forget about updating it
-          if (result === null) {
-            return;
-          }
-
-          const [from, to] = result;
-          view.dispatch(view.state.tr.deleteRange(from, to || from));
-        }
+        view.dispatch(
+          view.state.tr.setMeta(uploadPlaceholderPlugin, {
+            remove: { id: upload.id },
+          })
+        );
 
         onShowToast(error.message || dictionary.fileUploadError);
       })
diff --git a/shared/editor/components/Styles.ts b/shared/editor/components/Styles.ts
index 79890b4ea..056826ddc 100644
--- a/shared/editor/components/Styles.ts
+++ b/shared/editor/components/Styles.ts
@@ -427,6 +427,42 @@ li {
   }
 }
 
+.file.placeholder {
+  display: flex;
+  align-items: center;
+  background: ${props.theme.background};
+  box-shadow: 0 0 0 1px ${props.theme.divider};
+  white-space: nowrap;
+  border-radius: 8px;
+  padding: 6px 8px;
+  max-width: 840px;
+  cursor: default;
+
+  margin-top: 0.5em;
+  margin-bottom: 0.5em;
+
+  .title,
+  .subtitle {
+    margin-left: 8px;
+  }
+
+  .title {
+    font-weight: 600;
+    font-size: 14px;
+    color:  ${props.theme.text};
+  }
+
+  .subtitle {
+    font-size: 13px;
+    color: ${props.theme.textTertiary};
+    line-height: 0;
+  }
+
+  span {
+    font-family: ${props.theme.fontFamilyMono};
+  }
+}
+
 .image-replacement-uploading {
   img {
     opacity: 0.5;
diff --git a/shared/editor/extensions/Mermaid.ts b/shared/editor/extensions/Mermaid.ts
index 12db17aef..15c660c30 100644
--- a/shared/editor/extensions/Mermaid.ts
+++ b/shared/editor/extensions/Mermaid.ts
@@ -11,6 +11,7 @@ import {
 import { Decoration, DecorationSet } from "prosemirror-view";
 import { v4 as uuidv4 } from "uuid";
 import { isCode } from "../lib/isCode";
+import { isRemoteTransaction } from "../lib/multiplayer";
 import { findBlockNodes, NodeWithPos } from "../queries/findChildren";
 
 type MermaidState = {
@@ -251,7 +252,6 @@ export default function Mermaid({
         const previousNodeName = oldState.selection.$head.parent.type.name;
         const codeBlockChanged =
           transaction.docChanged && [nodeName, previousNodeName].includes(name);
-        const ySyncEdit = !!transaction.getMeta("y-sync$");
         const themeMeta = transaction.getMeta("theme");
         const mermaidMeta = transaction.getMeta("mermaid");
         const themeToggled = themeMeta?.isDark !== undefined;
@@ -260,7 +260,12 @@ export default function Mermaid({
           pluginState.isDark = themeMeta.isDark;
         }
 
-        if (mermaidMeta || themeToggled || codeBlockChanged || ySyncEdit) {
+        if (
+          mermaidMeta ||
+          themeToggled ||
+          codeBlockChanged ||
+          isRemoteTransaction(transaction)
+        ) {
           return getNewState({
             doc: transaction.doc,
             name,
diff --git a/shared/editor/extensions/Prism.ts b/shared/editor/extensions/Prism.ts
index a0fc017ff..e81700b9b 100644
--- a/shared/editor/extensions/Prism.ts
+++ b/shared/editor/extensions/Prism.ts
@@ -4,6 +4,7 @@ import { Node } from "prosemirror-model";
 import { Plugin, PluginKey, Transaction } from "prosemirror-state";
 import { Decoration, DecorationSet } from "prosemirror-view";
 import refractor from "refractor/core";
+import { isRemoteTransaction } from "../lib/multiplayer";
 import { findBlockNodes } from "../queries/findChildren";
 
 export const LANGUAGES = {
@@ -199,9 +200,12 @@ export default function Prism({
         const previousNodeName = oldState.selection.$head.parent.type.name;
         const codeBlockChanged =
           transaction.docChanged && [nodeName, previousNodeName].includes(name);
-        const ySyncEdit = !!transaction.getMeta("y-sync$");
 
-        if (!highlighted || codeBlockChanged || ySyncEdit) {
+        if (
+          !highlighted ||
+          codeBlockChanged ||
+          isRemoteTransaction(transaction)
+        ) {
           highlighted = true;
           return getDecorations({ doc: transaction.doc, name, lineNumbers });
         }
diff --git a/shared/editor/lib/multiplayer.ts b/shared/editor/lib/multiplayer.ts
new file mode 100644
index 000000000..685b2b66d
--- /dev/null
+++ b/shared/editor/lib/multiplayer.ts
@@ -0,0 +1,15 @@
+import { ySyncPluginKey } from "@getoutline/y-prosemirror";
+import { Transaction } from "prosemirror-state";
+
+/**
+ * Checks if a transaction is a remote transaction
+ *
+ * @param tr The Prosemirror transaction
+ * @returns true if the transaction is a remote transaction
+ */
+export function isRemoteTransaction(tr: Transaction): boolean {
+  const meta = tr.getMeta(ySyncPluginKey);
+
+  // This logic seems to be flipped? But it's correct.
+  return !!meta?.isChangeOrigin;
+}
diff --git a/shared/editor/lib/uploadPlaceholder.tsx b/shared/editor/lib/uploadPlaceholder.tsx
index 5c55fa60f..26ebb4b39 100644
--- a/shared/editor/lib/uploadPlaceholder.tsx
+++ b/shared/editor/lib/uploadPlaceholder.tsx
@@ -1,5 +1,9 @@
 import { EditorState, Plugin } from "prosemirror-state";
 import { Decoration, DecorationSet } from "prosemirror-view";
+import * as React from "react";
+import ReactDOM from "react-dom";
+import FileExtension from "../components/FileExtension";
+import { isRemoteTransaction } from "./multiplayer";
 import { recreateTransform } from "./prosemirror-recreate-transform";
 
 // based on the example at: https://prosemirror.net/examples/upload/
@@ -9,10 +13,15 @@ const uploadPlaceholder = new Plugin({
       return DecorationSet.empty;
     },
     apply(tr, set: DecorationSet) {
-      const ySyncEdit = !!tr.getMeta("y-sync$");
       let mapping = tr.mapping;
 
-      if (ySyncEdit) {
+      // See if the transaction adds or removes any placeholders – the placeholder display is
+      // different depending on if we're uploading an image, video or plain file
+      const action = tr.getMeta(this);
+
+      // Note: We always rebuild the mapping if the transaction comes from this plugin as otherwise
+      // with the default mapping decorations are wiped out when you upload multiple files at a time.
+      if (isRemoteTransaction(tr) || action) {
         try {
           mapping = recreateTransform(tr.before, tr.doc, {
             complexSteps: true,
@@ -27,9 +36,6 @@ const uploadPlaceholder = new Plugin({
 
       set = set.map(mapping, tr.doc);
 
-      // See if the transaction adds or removes any placeholders
-      const action = tr.getMeta(this);
-
       if (action?.add) {
         if (action.add.isImage) {
           if (action.add.replaceExisting) {
@@ -62,9 +68,7 @@ const uploadPlaceholder = new Plugin({
             });
             set = set.add(tr.doc, [deco]);
           }
-        }
-
-        if (action.add.isVideo) {
+        } else if (action.add.isVideo) {
           const element = document.createElement("div");
           element.className = "video placeholder";
 
@@ -75,6 +79,29 @@ const uploadPlaceholder = new Plugin({
 
           element.appendChild(video);
 
+          const deco = Decoration.widget(action.add.pos, element, {
+            id: action.add.id,
+          });
+          set = set.add(tr.doc, [deco]);
+        } else {
+          const element = document.createElement("div");
+          element.className = "file placeholder";
+
+          const icon = document.createElement("div");
+          const title = document.createElement("div");
+          title.className = "title";
+          title.innerText = action.add.file.name;
+
+          const subtitle = document.createElement("div");
+          subtitle.className = "subtitle";
+          subtitle.innerText = "Uploading…";
+
+          ReactDOM.render(<FileExtension title={action.add.file.name} />, icon);
+
+          element.appendChild(icon);
+          element.appendChild(title);
+          element.appendChild(subtitle);
+
           const deco = Decoration.widget(action.add.pos, element, {
             id: action.add.id,
           });
@@ -99,6 +126,13 @@ const uploadPlaceholder = new Plugin({
 
 export default uploadPlaceholder;
 
+/**
+ * Find the position of a placeholder by its ID
+ *
+ * @param state The editor state
+ * @param id The placeholder ID
+ * @returns The placeholder position as a tuple of [from, to] or null if not found
+ */
 export function findPlaceholder(
   state: EditorState,
   id: string
diff --git a/shared/editor/queries/findAttachmentById.ts b/shared/editor/queries/findAttachmentById.ts
deleted file mode 100644
index 91968b977..000000000
--- a/shared/editor/queries/findAttachmentById.ts
+++ /dev/null
@@ -1,23 +0,0 @@
-import { EditorState } from "prosemirror-state";
-
-const findAttachmentById = function (
-  state: EditorState,
-  id: string
-): [number, number] | null {
-  let result: [number, number] | null = null;
-
-  state.doc.descendants((node, pos) => {
-    if (result) {
-      return false;
-    }
-    if (node.type.name === "attachment" && node.attrs.id === id) {
-      result = [pos, pos + node.nodeSize];
-      return false;
-    }
-    return true;
-  });
-
-  return result;
-};
-
-export default findAttachmentById;