diff --git a/app/menus/TableOfContentsMenu.tsx b/app/menus/TableOfContentsMenu.tsx
index 32daac5c5c..4adf176f47 100644
--- a/app/menus/TableOfContentsMenu.tsx
+++ b/app/menus/TableOfContentsMenu.tsx
@@ -3,6 +3,7 @@ import { TableOfContentsIcon } from "outline-icons";
 import { useMemo } from "react";
 import { useTranslation } from "react-i18next";
 import styled from "styled-components";
+import { EmojiText } from "@shared/components/EmojiText";
 import { createAction, createActionGroup } from "~/actions";
 import { ActiveDocumentSection } from "~/actions/sections";
 import Button from "~/components/Button";
@@ -26,7 +27,7 @@ function TableOfContentsMenu() {
           createAction({
             name: (
               <HeadingWrapper $level={heading.level - minHeading}>
-                {t(heading.title)}
+                <EmojiText>{heading.title}</EmojiText>
               </HeadingWrapper>
             ),
             section: ActiveDocumentSection,
@@ -38,7 +39,7 @@ function TableOfContentsMenu() {
               ),
           })
         ),
-    [t, headings, minHeading]
+    [headings, minHeading]
   );
 
   const actions = useMemo(() => {
diff --git a/app/scenes/Document/components/Contents.tsx b/app/scenes/Document/components/Contents.tsx
index 3818a1b107..7a19e7c5ba 100644
--- a/app/scenes/Document/components/Contents.tsx
+++ b/app/scenes/Document/components/Contents.tsx
@@ -4,6 +4,7 @@ import { useState, useEffect, useRef } from "react";
 import { useTranslation } from "react-i18next";
 import styled from "styled-components";
 import breakpoint from "styled-components-breakpoint";
+import { EmojiText } from "@shared/components/EmojiText";
 import { EditorStyleHelper } from "@shared/editor/styles/EditorStyleHelper";
 import { depths, hideScrollbars, s } from "@shared/styles";
 import { useDocumentContext } from "~/components/DocumentContext";
@@ -80,7 +81,9 @@ function Contents() {
               level={heading.level - headingAdjustment}
               active={activeSlug === heading.id}
             >
-              <Link href={`#${heading.id}`}>{heading.title}</Link>
+              <Link href={`#${heading.id}`}>
+                <EmojiText>{heading.title}</EmojiText>
+              </Link>
             </ListItem>
           ))}
       </List>
diff --git a/shared/components/EmojiText.tsx b/shared/components/EmojiText.tsx
new file mode 100644
index 0000000000..dbc01ae1c8
--- /dev/null
+++ b/shared/components/EmojiText.tsx
@@ -0,0 +1,66 @@
+import { isUUID } from "validator";
+import { getEmojiFromName } from "../editor/lib/emoji";
+import { CustomEmoji } from "./CustomEmoji";
+
+type Props = {
+  /** The text to render, which may contain emoji shortcodes like :smile: or :uuid: */
+  children: string;
+  /** Size of rendered custom emojis */
+  emojiSize?: number | string;
+};
+
+// Matches emoji shortcodes like :smile: or :550e8400-e29b-41d4-a716-446655440000:
+const emojiShortcodeRegex = /:([a-zA-Z0-9_-]+):/g;
+
+/**
+ * Renders text with embedded emoji shortcodes. Standard emoji shortcodes like
+ * :smile: are converted to native emoji characters, while UUID shortcodes are
+ * rendered as custom emoji images.
+ *
+ * @param props.children - the text to render, which may contain emoji shortcodes.
+ * @param props.emojiSize - size of rendered custom emojis.
+ * @returns a React element with text and inline emojis.
+ */
+export function EmojiText({ children, emojiSize = "1em" }: Props) {
+  const parts: (string | JSX.Element)[] = [];
+  let lastIndex = 0;
+  let match: RegExpExecArray | null;
+  let key = 0;
+
+  while ((match = emojiShortcodeRegex.exec(children)) !== null) {
+    // Add text before the match
+    if (match.index > lastIndex) {
+      parts.push(children.slice(lastIndex, match.index));
+    }
+
+    const shortcode = match[1];
+
+    if (isUUID(shortcode)) {
+      // Custom emoji - render as image
+      parts.push(
+        <CustomEmoji key={key++} value={shortcode} size={emojiSize} />
+      );
+    } else {
+      // Standard emoji - convert to native character
+      const emoji = getEmojiFromName(shortcode);
+      if (emoji !== "?") {
+        parts.push(emoji);
+      } else {
+        // Unknown shortcode, keep original text
+        parts.push(match[0]);
+      }
+    }
+
+    lastIndex = match.index + match[0].length;
+  }
+
+  // Add remaining text after last match
+  if (lastIndex < children.length) {
+    parts.push(children.slice(lastIndex));
+  }
+
+  // Reset regex state for next call
+  emojiShortcodeRegex.lastIndex = 0;
+
+  return <>{parts}</>;
+}
diff --git a/shared/editor/nodes/Emoji.tsx b/shared/editor/nodes/Emoji.tsx
index 46702db433..f42dc5b673 100644
--- a/shared/editor/nodes/Emoji.tsx
+++ b/shared/editor/nodes/Emoji.tsx
@@ -63,7 +63,15 @@ export default class Emoji extends Extension {
           getEmojiFromName(name),
         ];
       },
-      leafText: (node) => getEmojiFromName(node.attrs["data-name"]),
+      leafText: (node) => {
+        const name = node.attrs["data-name"];
+        // Custom emojis are stored as UUIDs, preserve the shortcode format
+        // so they can be rendered by EmojiText component
+        if (isUUID(name)) {
+          return `:${name}:`;
+        }
+        return getEmojiFromName(name);
+      },
     };
   }