diff --git a/docs-contributors/ui-reference.md b/docs-contributors/ui-reference.md
index 4055cae1c8..5a942e610b 100644
--- a/docs-contributors/ui-reference.md
+++ b/docs-contributors/ui-reference.md
@@ -338,6 +338,23 @@ Here is an image:
 When including the partial, the docs engine will rewrite the link path to load
 the image in `docs/img/screenshot.png`.
 
+## Tables of Contents
+
+You can add a list of links to pages in the current directory by adding the
+following line to a docs page:
+
+```
+(!toc!)
+```
+
+The docs engine replaces this line with a list of links to pages in the current
+directory, using the title and description of each page to populate the link:
+
+```
+- [Page 1](page1.mdx): This is a description of Page 1.
+- [Page 2](page2.mdx): This is a description of Page 2.
+```
+
 ## Tabs
 
 To insert a tabs block like the one above, use this syntax:
diff --git a/server/fixtures/toc/database-access/database-access.mdx b/server/fixtures/toc/database-access/database-access.mdx
new file mode 100644
index 0000000000..b2d241c9e6
--- /dev/null
+++ b/server/fixtures/toc/database-access/database-access.mdx
@@ -0,0 +1,4 @@
+---
+title: Protect Databases with Teleport
+description: Guides to protecting databases with Teleport.
+---
diff --git a/server/fixtures/toc/database-access/mysql.mdx b/server/fixtures/toc/database-access/mysql.mdx
new file mode 100644
index 0000000000..d4d3b4602e
--- /dev/null
+++ b/server/fixtures/toc/database-access/mysql.mdx
@@ -0,0 +1,4 @@
+---
+title: Protect MySQL with Teleport
+description: How to enroll your MySQL database with Teleport
+---
diff --git a/server/fixtures/toc/database-access/postgres.mdx b/server/fixtures/toc/database-access/postgres.mdx
new file mode 100644
index 0000000000..5b5c52a58a
--- /dev/null
+++ b/server/fixtures/toc/database-access/postgres.mdx
@@ -0,0 +1,4 @@
+---
+title: Protect Postgres with Teleport
+description: How to enroll Postgres with your Teleport cluster
+---
diff --git a/server/fixtures/toc/database-access/source.mdx b/server/fixtures/toc/database-access/source.mdx
new file mode 100644
index 0000000000..d89f98fd6c
--- /dev/null
+++ b/server/fixtures/toc/database-access/source.mdx
@@ -0,0 +1,5 @@
+## Header
+
+Here is an intro.
+
+(!toc!)
diff --git a/server/fixtures/toc/expected.mdx b/server/fixtures/toc/expected.mdx
new file mode 100644
index 0000000000..9cbec5eee8
--- /dev/null
+++ b/server/fixtures/toc/expected.mdx
@@ -0,0 +1,7 @@
+## Header
+
+Here is an intro.
+
+*   [Protect Databases with Teleport](database-access.mdx): Guides to protecting databases with Teleport.
+*   [Protect MySQL with Teleport](mysql.mdx): How to enroll your MySQL database with Teleport
+*   [Protect Postgres with Teleport](postgres.mdx): How to enroll Postgres with your Teleport cluster
diff --git a/server/markdown-config.ts b/server/markdown-config.ts
index 02c71a4eb9..053654667d 100644
--- a/server/markdown-config.ts
+++ b/server/markdown-config.ts
@@ -16,6 +16,7 @@ import remarkVariables from "./remark-variables";
 import remarkCodeSnippet from "./remark-code-snippet";
 import remarkParse from "remark-parse";
 import remarkRehype from "remark-rehype";
+import remarkTOC from "./remark-toc";
 import remarkCopyLinkedFiles from "remark-copy-linked-files";
 import rehypeImages from "./rehype-images";
 import { getVersion, getVersionRootPath } from "./docs-helpers";
@@ -42,6 +43,8 @@ export const transformToAST = async (value: string, vfile: VFile) => {
 
   // run() will apply plugins and return modified AST
   const AST = await unified()
+    // Resolves (!toc dir/path!) syntax
+    .use(remarkTOC)
     .use(remarkIncludes, {
       rootDir: getVersionRootPath(vfile.path),
     }) // Resolves (!include.ext!) syntax
diff --git a/server/remark-toc.ts b/server/remark-toc.ts
new file mode 100644
index 0000000000..e12448945b
--- /dev/null
+++ b/server/remark-toc.ts
@@ -0,0 +1,120 @@
+import * as nodeFS from "fs";
+import path from "path";
+import matter from "gray-matter";
+import { visitParents } from "unist-util-visit-parents";
+import { fromMarkdown } from "mdast-util-from-markdown";
+import type { Parent } from "unist";
+import type { VFile } from "vfile";
+import type { Content } from "mdast";
+import type { Transformer } from "unified";
+
+// relativePathToFile takes a filepath and returns a path we can use in links
+// to the file in a table of contents page. The link path is a relative path
+// to the directory where we are placing the table of contents page.
+// @param root {string} - the directory path to the table of contents page.
+// @param filepath {string} - the path from which to generate a link path.
+const relativePathToFile = (root: string, filepath: string) => {
+  // Return the filepath without the first segment, removing the first
+  // slash. This is because the TOC file we are generating is located at
+  // root.
+  return filepath.slice(root.length).replace(/^\//, "");
+};
+
+// getTOC generates a list of links to all files in the same directory as
+// filePath except for filePath. The return value is an object with two
+// properties:
+// - result: a string containing the resulting list of links.
+// - error: an error message encountered during processing
+export const getTOC = (filePath: string, fs = nodeFS) => {
+  const dirPath = path.dirname(filePath);
+  if (!fs.existsSync(dirPath)) {
+    return {
+      error: `Cannot generate a table of contents for nonexistent directory at ${dirPath}`,
+    };
+  }
+
+  const { name } = path.parse(filePath);
+
+  const files = fs.readdirSync(dirPath, "utf8");
+  let mdxFiles = new Set();
+  const dirs = files.reduce((accum, current) => {
+    // Don't add a TOC entry for the current file.
+    if (name == path.parse(current).name) {
+      return accum;
+    }
+    const stats = fs.statSync(path.join(dirPath, current));
+    if (!stats.isDirectory() && current.endsWith(".mdx")) {
+      mdxFiles.add(path.join(dirPath, current));
+      return accum;
+    }
+    accum.add(path.join(dirPath, current));
+    return accum;
+  }, new Set());
+
+  // Add rows to the menu page for non-menu pages.
+  let entries = [];
+  mdxFiles.forEach((f: string, idx: number) => {
+    const text = fs.readFileSync(f, "utf8");
+    let relPath = relativePathToFile(dirPath, f);
+    const { data } = matter(text);
+    entries.push(`- [${data.title}](${relPath}): ${data.description}`);
+  });
+
+  // Add rows to the menu page for first-level child menu pages
+  dirs.forEach((f: string, idx: number) => {
+    const menuPath = path.join(f, path.parse(f).base + ".mdx");
+    if (!fs.existsSync(menuPath)) {
+      return {
+        error: `there must be a page called ${menuPath} that introduces ${f}`,
+      };
+    }
+    const text = fs.readFileSync(menuPath, "utf8");
+    let relPath = relativePathToFile(dirPath, menuPath);
+    const { data } = matter(text);
+
+    entries.push(`- [${data.title}](${relPath}): ${data.description}`);
+  });
+  entries.sort();
+  return { result: entries.join("\n") };
+};
+
+const tocRegexpPattern = "^\\(!toc!\\)$";
+
+// remarkTOC replaces (!toc!) syntax in a page with a list of docs pages at a
+// given directory location.
+export default function remarkTOC(): Transformer {
+  return (root: Content, vfile: VFile) => {
+    const lastErrorIndex = vfile.messages.length;
+
+    visitParents(root, (node, ancestors: Parent[]) => {
+      if (node.type !== "text") {
+        return;
+      }
+      const parent = ancestors[ancestors.length - 1];
+
+      if (parent.type !== "paragraph") {
+        return;
+      }
+      if (!parent.children || parent.children.length !== 1) {
+        return;
+      }
+
+      const tocExpr = node.value.trim().match(tocRegexpPattern);
+      if (!tocExpr) {
+        return;
+      }
+
+      const { result, error } = getTOC(vfile.path);
+      if (!!error) {
+        vfile.message(error, node);
+        return;
+      }
+      const tree = fromMarkdown(result, {});
+
+      const grandParent = ancestors[ancestors.length - 2] as Parent;
+      const parentIndex = grandParent.children.indexOf(parent);
+
+      grandParent.children.splice(parentIndex, 1, ...tree.children);
+    });
+  };
+}
diff --git a/uvu-tests/remark-toc.test.ts b/uvu-tests/remark-toc.test.ts
new file mode 100644
index 0000000000..d0390f9be7
--- /dev/null
+++ b/uvu-tests/remark-toc.test.ts
@@ -0,0 +1,185 @@
+import { Volume, createFsFromVolume } from "memfs";
+import { default as remarkTOC, getTOC } from "../server/remark-toc";
+import { readFileSync } from "fs";
+import { resolve } from "path";
+import { suite } from "uvu";
+import * as assert from "uvu/assert";
+import { VFile, VFileOptions } from "vfile";
+import remarkMdx from "remark-mdx";
+import remarkGFM from "remark-gfm";
+import { remark } from "remark";
+
+const Suite = suite("server/remark-toc");
+
+const testFilesTwoSections = {
+  "/docs/docs.mdx": `---
+title: "Documentation Home"
+description: "Guides to setting up the product."
+---
+
+Guides to setting up the product.
+
+`,
+  "/docs/database-access/database-access.mdx": `---
+title: "Database Access"
+description: Guides related to Database Access.
+---
+
+Guides related to Database Access.
+
+`,
+  "/docs/database-access/page1.mdx": `---
+title: "Database Access Page 1"
+description: "Protecting DB 1 with Teleport"
+---`,
+  "/docs/database-access/page2.mdx": `---
+title: "Database Access Page 2"
+description: "Protecting DB 2 with Teleport"
+---`,
+  "/docs/application-access/application-access.mdx": `---
+title: "Application Access"
+description: "Guides related to Application Access"
+---
+
+Guides related to Application Access.
+
+`,
+  "/docs/application-access/page1.mdx": `---
+title: "Application Access Page 1"
+description: "Protecting App 1 with Teleport"
+---`,
+  "/docs/application-access/page2.mdx": `---
+title: "Application Access Page 2"
+description: "Protecting App 2 with Teleport"
+---`,
+};
+
+Suite("getTOC with one link to a directory", () => {
+  const expected = `- [Application Access](application-access/application-access.mdx): Guides related to Application Access`;
+
+  const vol = Volume.fromJSON({
+    "/docs/docs.mdx": `---
+title: Documentation Home
+description: Guides for setting up the product.
+---
+
+Guides for setting up the product.
+
+`,
+    "/docs/application-access/application-access.mdx": `---
+title: "Application Access"
+description: "Guides related to Application Access"
+---
+
+`,
+    "/docs/application-access/page1.mdx": `---
+title: "Application Access Page 1"
+description: "Protecting App 1 with Teleport"
+---`,
+    "/docs/application-access/page2.mdx": `---
+title: "Application Access Page 2"
+description: "Protecting App 2 with Teleport"
+---`,
+  });
+  const fs = createFsFromVolume(vol);
+  const actual = getTOC("/docs/docs.mdx", fs);
+  assert.equal(actual.result, expected);
+});
+
+Suite("getTOC with multiple links to directories", () => {
+  const expected = `- [Application Access](application-access/application-access.mdx): Guides related to Application Access
+- [Database Access](database-access/database-access.mdx): Guides related to Database Access.`;
+
+  const vol = Volume.fromJSON(testFilesTwoSections);
+  const fs = createFsFromVolume(vol);
+  const actual = getTOC("/docs/docs.mdx", fs);
+  assert.equal(actual.result, expected);
+});
+
+Suite("getTOC orders sections correctly", () => {
+  const expected = `- [API Usage](api.mdx): Using the API.
+- [Application Access](application-access/application-access.mdx): Guides related to Application Access
+- [Desktop Access](desktop-access/desktop-access.mdx): Guides related to Desktop Access
+- [Initial Setup](initial-setup.mdx): How to set up the product for the first time.
+- [Kubernetes](kubernetes.mdx): A guide related to Kubernetes.`;
+
+  const vol = Volume.fromJSON({
+    "/docs/docs.mdx": `---
+title: Documentation Home
+description: Guides to setting up the product.
+---
+
+Guides to setting up the product.
+
+`,
+    "/docs/desktop-access/desktop-access.mdx": `---
+title: "Desktop Access"
+description: "Guides related to Desktop Access"
+---
+
+`,
+
+    "/docs/application-access/application-access.mdx": `---
+title: "Application Access"
+description: "Guides related to Application Access"
+---
+
+`,
+    "/docs/desktop-access/get-started.mdx": `---
+title: "Get Started"
+description: "Get started with desktop access."
+---`,
+    "/docs/application-access/page1.mdx": `---
+title: "Application Access Page 1"
+description: "Protecting App 1 with Teleport"
+---`,
+    "/docs/kubernetes.mdx": `---
+title: "Kubernetes"
+description: "A guide related to Kubernetes."
+---`,
+
+    "/docs/initial-setup.mdx": `---
+title: "Initial Setup"
+description: "How to set up the product for the first time."
+---`,
+    "/docs/api.mdx": `---
+title: "API Usage"
+description: "Using the API."
+---`,
+  });
+  const fs = createFsFromVolume(vol);
+  const actual = getTOC("/docs/docs.mdx", fs);
+  assert.equal(actual.result, expected);
+});
+
+const transformer = (vfileOptions: VFileOptions) => {
+  const file = new VFile(vfileOptions);
+
+  return remark()
+    .use(remarkMdx)
+    .use(remarkGFM)
+    .use(remarkTOC)
+    .processSync(file);
+};
+
+Suite("replaces inclusion expressions", () => {
+  const sourcePath = "server/fixtures/toc/database-access/source.mdx";
+  const value = readFileSync(resolve(sourcePath), "utf-8");
+
+  const result = transformer({
+    value,
+    path: sourcePath,
+  });
+
+  const actual = result.toString();
+
+  const expected = readFileSync(
+    resolve("server/fixtures/toc/expected.mdx"),
+    "utf-8"
+  );
+
+  assert.equal(result.messages, []);
+  assert.equal(actual, expected);
+});
+
+Suite.run();