diff --git a/app/components/ContextMenu/MenuItem.js b/app/components/ContextMenu/MenuItem.js
index a82d9222c..7ebc4bc9a 100644
--- a/app/components/ContextMenu/MenuItem.js
+++ b/app/components/ContextMenu/MenuItem.js
@@ -15,6 +15,7 @@ type Props = {|
   target?: "_blank",
   as?: string | React.ComponentType<*>,
   hide?: () => void,
+  level?: number,
 |};
 
 const MenuItem = ({
@@ -86,6 +87,7 @@ const Spacer = styled.svg`
 export const MenuAnchor = styled.a`
   display: flex;
   margin: 0;
+  margin-left: ${(props) => props.level * 10}px;
   border: 0;
   padding: 12px;
   width: 100%;
diff --git a/app/components/ContextMenu/Template.js b/app/components/ContextMenu/Template.js
index bbd3bd120..f8a2507ca 100644
--- a/app/components/ContextMenu/Template.js
+++ b/app/components/ContextMenu/Template.js
@@ -9,6 +9,7 @@ import {
   MenuItem as BaseMenuItem,
 } from "reakit/Menu";
 import styled from "styled-components";
+import Header from "./Header";
 import MenuItem, { MenuAnchor } from "./MenuItem";
 import Separator from "./Separator";
 import ContextMenu from ".";
@@ -34,6 +35,7 @@ type TMenuItem =
       visible?: boolean,
       selected?: boolean,
       disabled?: boolean,
+      level?: number,
     |}
   | {|
       title: React.Node,
@@ -128,7 +130,8 @@ function Template({ items, ...menu }: Props): React.Node {
           key={index}
           disabled={item.disabled}
           selected={item.selected}
-          target="_blank"
+          level={item.level}
+          target={item.href.startsWith("#") ? undefined : "_blank"}
           {...menu}
         >
           {item.title}
@@ -167,6 +170,10 @@ function Template({ items, ...menu }: Props): React.Node {
       return <Separator key={index} />;
     }
 
+    if (item.type === "heading") {
+      return <Header>{item.title}</Header>;
+    }
+
     return null;
   });
 }
diff --git a/app/menus/TableOfContentsMenu.js b/app/menus/TableOfContentsMenu.js
new file mode 100644
index 000000000..abe1f9780
--- /dev/null
+++ b/app/menus/TableOfContentsMenu.js
@@ -0,0 +1,66 @@
+// @flow
+import { observer } from "mobx-react";
+import { TableOfContentsIcon } from "outline-icons";
+import * as React from "react";
+import { useTranslation } from "react-i18next";
+import { MenuButton, useMenuState } from "reakit/Menu";
+import Button from "components/Button";
+import ContextMenu from "components/ContextMenu";
+import Template from "components/ContextMenu/Template";
+
+type Props = {|
+  headings: { title: string, level: number, id: string }[],
+|};
+
+function TableOfContentsMenu({ headings }: Props) {
+  const menu = useMenuState({
+    modal: true,
+    unstable_preventOverflow: true,
+    unstable_fixed: true,
+    unstable_flip: true,
+  });
+
+  const { t } = useTranslation();
+
+  const minHeading = headings.reduce(
+    (memo, heading) => (heading.level < memo ? heading.level : memo),
+    Infinity
+  );
+
+  return (
+    <>
+      <MenuButton {...menu}>
+        {(props) => (
+          <Button
+            {...props}
+            icon={<TableOfContentsIcon />}
+            iconColor="currentColor"
+            borderOnHover
+            neutral
+          />
+        )}
+      </MenuButton>
+      <ContextMenu {...menu} aria-label={t("Table of contents")}>
+        <Template
+          {...menu}
+          items={[
+            {
+              type: "heading",
+              visible: true,
+              title: t("Contents"),
+            },
+            ...headings.map((heading) => {
+              return {
+                href: `#${heading.id}`,
+                title: t(heading.title),
+                level: heading.level - minHeading,
+              };
+            }),
+          ]}
+        />
+      </ContextMenu>
+    </>
+  );
+}
+
+export default observer(TableOfContentsMenu);
diff --git a/app/scenes/Document/components/Document.js b/app/scenes/Document/components/Document.js
index 726c4ee52..03a65ba7b 100644
--- a/app/scenes/Document/components/Document.js
+++ b/app/scenes/Document/components/Document.js
@@ -374,6 +374,7 @@ class DocumentScene extends React.Component<Props> {
               sharedTree={this.props.sharedTree}
               goBack={this.goBack}
               onSave={this.onSave}
+              headings={headings}
             />
             <MaxWidth
               archived={document.isArchived}
diff --git a/app/scenes/Document/components/Header.js b/app/scenes/Document/components/Header.js
index 5b36a6b1c..7a4b51088 100644
--- a/app/scenes/Document/components/Header.js
+++ b/app/scenes/Document/components/Header.js
@@ -24,6 +24,7 @@ import useMobile from "hooks/useMobile";
 import useStores from "hooks/useStores";
 import DocumentMenu from "menus/DocumentMenu";
 import NewChildDocumentMenu from "menus/NewChildDocumentMenu";
+import TableOfContentsMenu from "menus/TableOfContentsMenu";
 import TemplatesMenu from "menus/TemplatesMenu";
 import { type NavigationNode } from "types";
 import { metaDisplay } from "utils/keyboard";
@@ -46,6 +47,7 @@ type Props = {|
     publish?: boolean,
     autosave?: boolean,
   }) => void,
+  headings: { title: string, level: number, id: string }[],
 |};
 
 function DocumentHeader({
@@ -60,6 +62,7 @@ function DocumentHeader({
   publishingIsDisabled,
   sharedTree,
   onSave,
+  headings,
 }: Props) {
   const { t } = useTranslation();
   const { auth, ui, policies } = useStores();
@@ -153,6 +156,11 @@ function DocumentHeader({
         }
         actions={
           <>
+            {isMobile && (
+              <TocWrapper>
+                <TableOfContentsMenu headings={headings} />
+              </TocWrapper>
+            )}
             {!isPublishing && isSaving && <Status>{t("Saving")}…</Status>}
             <Collaborators
               document={document}
@@ -274,4 +282,9 @@ const Status = styled(Action)`
   color: ${(props) => props.theme.slate};
 `;
 
+const TocWrapper = styled(Action)`
+  position: absolute;
+  left: 42px;
+`;
+
 export default observer(DocumentHeader);
diff --git a/shared/i18n/locales/en_US/translation.json b/shared/i18n/locales/en_US/translation.json
index 7d42aee8a..6b68be10d 100644
--- a/shared/i18n/locales/en_US/translation.json
+++ b/shared/i18n/locales/en_US/translation.json
@@ -206,6 +206,7 @@
   "Share options": "Share options",
   "Go to document": "Go to document",
   "Revoke link": "Revoke link",
+  "Table of contents": "Table of contents",
   "By {{ author }}": "By {{ author }}",
   "Are you sure you want to make {{ userName }} an admin? Admins can modify team and billing information.": "Are you sure you want to make {{ userName }} an admin? Admins can modify team and billing information.",
   "Are you sure you want to make {{ userName }} a member?": "Are you sure you want to make {{ userName }} a member?",
@@ -337,7 +338,6 @@
   "Move current document": "Move current document",
   "Jump to search": "Jump to search",
   "Jump to home": "Jump to home",
-  "Table of contents": "Table of contents",
   "Toggle navigation": "Toggle navigation",
   "Focus search input": "Focus search input",
   "Open this guide": "Open this guide",