diff --git a/server/models/helpers/DocumentHelper.tsx b/server/models/helpers/DocumentHelper.tsx
index ff42056a1..3aca06544 100644
--- a/server/models/helpers/DocumentHelper.tsx
+++ b/server/models/helpers/DocumentHelper.tsx
@@ -19,9 +19,7 @@ import {
 import attachmentCreator from "@server/commands/attachmentCreator";
 import { parser, schema } from "@server/editor";
 import { trace } from "@server/logging/tracing";
-import type Document from "@server/models/Document";
-import type Revision from "@server/models/Revision";
-import User from "@server/models/User";
+import { Document, Revision, User } from "@server/models";
 import FileStorage from "@server/storage/files";
 import diff from "@server/utils/diff";
 import parseAttachmentIds from "@server/utils/parseAttachmentIds";
@@ -112,10 +110,19 @@ export default class DocumentHelper {
       centered: options?.centered,
     });
 
-    if (options?.signedUrls && "teamId" in document) {
+    if (options?.signedUrls) {
+      const teamId =
+        document instanceof Document
+          ? document.teamId
+          : (await document.$get("document"))?.teamId;
+
+      if (!teamId) {
+        return output;
+      }
+
       output = await DocumentHelper.attachmentsToSignedUrls(
         output,
-        document.teamId,
+        teamId,
         typeof options.signedUrls === "number" ? options.signedUrls : undefined
       );
     }
@@ -145,10 +152,10 @@ export default class DocumentHelper {
   static async diff(
     before: Document | Revision | null,
     after: Revision,
-    options?: HTMLOptions
+    { signedUrls, ...options }: HTMLOptions = {}
   ) {
     if (!before) {
-      return await DocumentHelper.toHTML(after, options);
+      return await DocumentHelper.toHTML(after, { ...options, signedUrls });
     }
 
     const beforeHTML = await DocumentHelper.toHTML(before, options);
@@ -158,11 +165,27 @@ export default class DocumentHelper {
 
     // Extract the content from the article tag and diff the HTML, we don't
     // care about the surrounding layout and stylesheets.
-    const diffedContentAsHTML = diff(
+    let diffedContentAsHTML = diff(
       beforeDOM.window.document.getElementsByTagName("article")[0].innerHTML,
       afterDOM.window.document.getElementsByTagName("article")[0].innerHTML
     );
 
+    // Sign only the URLS in the diffed content
+    if (signedUrls) {
+      const teamId =
+        before instanceof Document
+          ? before.teamId
+          : (await before.$get("document"))?.teamId;
+
+      if (teamId) {
+        diffedContentAsHTML = await DocumentHelper.attachmentsToSignedUrls(
+          diffedContentAsHTML,
+          teamId,
+          typeof signedUrls === "number" ? signedUrls : undefined
+        );
+      }
+    }
+
     // Inject the diffed content into the original document with styling and
     // serialize back to a string.
     const article = beforeDOM.window.document.querySelector("article");
@@ -318,6 +341,7 @@ export default class DocumentHelper {
     expiresIn = 3000
   ) {
     const attachmentIds = parseAttachmentIds(text);
+
     await Promise.all(
       attachmentIds.map(async (id) => {
         const attachment = await Attachment.findOne({
@@ -332,6 +356,7 @@ export default class DocumentHelper {
             attachment.key,
             expiresIn
           );
+
           text = text.replace(
             new RegExp(escapeRegExp(attachment.redirectUrl), "g"),
             signedUrl
diff --git a/server/storage/files/LocalStorage.ts b/server/storage/files/LocalStorage.ts
index 500dcd8e3..631a978bc 100644
--- a/server/storage/files/LocalStorage.ts
+++ b/server/storage/files/LocalStorage.ts
@@ -114,7 +114,7 @@ export default class LocalStorage extends BaseStorage {
         expiresIn,
       }
     );
-    return Promise.resolve(`/api/files.get?sig=${sig}`);
+    return Promise.resolve(`${env.URL}/api/files.get?sig=${sig}`);
   };
 
   public getFileStream(key: string) {
diff --git a/shared/editor/components/Styles.ts b/shared/editor/components/Styles.ts
index 056826ddc..906d070d0 100644
--- a/shared/editor/components/Styles.ts
+++ b/shared/editor/components/Styles.ts
@@ -249,6 +249,17 @@ const findAndReplaceStyle = () => css`
   }
 `;
 
+const emailStyle = (props: Props) => css`
+  .attachment {
+    display: block;
+    color: ${props.theme.text} !important;
+    box-shadow: 0 0 0 1px ${props.theme.divider};
+    white-space: nowrap;
+    border-radius: 8px;
+    padding: 6px 8px;
+  }
+`;
+
 const style = (props: Props) => `
 flex-grow: ${props.grow ? 1 : 0};
 justify-content: start;
@@ -1546,6 +1557,7 @@ const EditorContainer = styled.div<Props>`
   ${codeMarkCursor}
   ${codeBlockStyle}
   ${findAndReplaceStyle}
+  ${emailStyle}
 `;
 
 export default EditorContainer;
diff --git a/shared/editor/rules/links.ts b/shared/editor/rules/links.ts
index 296a1dca6..0745e7bfd 100644
--- a/shared/editor/rules/links.ts
+++ b/shared/editor/rules/links.ts
@@ -29,6 +29,7 @@ function isAttachment(token: Token) {
     // external (public share are pre-signed and this is a reasonable way of detecting them)
     href?.startsWith("/api/attachments.redirect") ||
     href?.startsWith("/api/files.get") ||
+    href?.startsWith(`${env.URL}/api/files.get`) ||
     ((href?.startsWith(env.AWS_S3_UPLOAD_BUCKET_URL) ||
       href?.startsWith(env.AWS_S3_ACCELERATE_URL)) &&
       href?.includes("X-Amz-Signature"))