diff --git a/assets/javascripts/app/app.js b/assets/javascripts/app/app.js
index 3ced2c403c..f05b963dd5 100644
--- a/assets/javascripts/app/app.js
+++ b/assets/javascripts/app/app.js
@@ -117,17 +117,18 @@ class App extends Events {
     delete this.DOC;
   }
 
-  bootAll() {
+  async bootAll() {
     const docs = this.settings.getDocs();
     for (var doc of this.DOCS) {
       (docs.includes(doc.slug) ? this.docs : this.disabledDocs).add(doc);
     }
+    delete this.DOCS;
     this.migrateDocs();
+    await this.migrateToLatestVersions();
     this.docs.load(this.start.bind(this), this.onBootError.bind(this), {
       readCache: true,
       writeCache: true,
     });
-    delete this.DOCS;
   }
 
   start() {
@@ -190,6 +191,86 @@ class App extends Events {
     }
   }
 
+  // With the "latest version" preference enabled, replace the enabled docs for
+  // which a newer version is available with that version.
+  async migrateToLatestVersions() {
+    if (!this.settings.get("autoLatestVersion")) {
+      return;
+    }
+
+    const allDocs = this.docs.all().concat(this.disabledDocs.all());
+    // The same version can supersede several enabled docs, so it's only loaded
+    // once, e.g. when both CMake 3.9 and CMake 3.10 are enabled.
+    const migrations = new Map();
+
+    for (const outdated of this.docs.all()) {
+      const latest = outdated.findLatestVersion(allDocs);
+      if (latest === outdated) {
+        continue;
+      }
+      if (!migrations.has(latest)) {
+        migrations.set(latest, []);
+      }
+      migrations.get(latest).push(outdated);
+    }
+
+    const loaded = await this.loadLatestVersions([...migrations.keys()]);
+    let needsSaving;
+
+    for (const [latest, outdatedDocs] of migrations) {
+      if (!loaded.has(latest)) {
+        continue;
+      }
+      for (const outdated of outdatedDocs) {
+        this.docs.remove(outdated);
+        this.disabledDocs.add(outdated);
+      }
+      if (!this.docs.contains(latest)) {
+        this.disabledDocs.remove(latest);
+        this.docs.add(latest);
+      }
+      needsSaving = true;
+    }
+
+    if (needsSaving) {
+      this.docs.sort();
+      this.saveDocs();
+    }
+  }
+
+  // Saving drops the offline data of the docs that are disabled, so the index
+  // of their latest version has to load before they are replaced. Loads no
+  // more docs at once than Docs#load does.
+  async loadLatestVersions(docs) {
+    const loaded = new Set();
+    let i = 0;
+
+    const next = async () => {
+      while (i < docs.length) {
+        const doc = docs[i++];
+        const success = await new Promise((resolve) =>
+          doc.load(
+            () => resolve(true),
+            () => resolve(false),
+            { readCache: true, writeCache: true },
+          ),
+        );
+        if (success) {
+          loaded.add(doc);
+        }
+      }
+    };
+
+    await Promise.all(
+      Array.from(
+        { length: Math.min(docs.length, app.collections.Docs.CONCURRENCY) },
+        next,
+      ),
+    );
+
+    return loaded;
+  }
+
   enableDoc(doc, _onSuccess, onError) {
     if (this.docs.contains(doc)) {
       return;
diff --git a/assets/javascripts/app/settings.js b/assets/javascripts/app/settings.js
index 617830ecc9..113005a65d 100644
--- a/assets/javascripts/app/settings.js
+++ b/assets/javascripts/app/settings.js
@@ -14,6 +14,7 @@ app.Settings = class Settings {
     "tips",
     "noAutofocus",
     "autoInstall",
+    "autoLatestVersion",
     "spaceScroll",
     "spaceTimeout",
     "noDocSpecificIcon",
@@ -40,6 +41,7 @@ app.Settings = class Settings {
     spaceScroll: 1,
     spaceTimeout: 0.5,
     noDocSpecificIcon: false,
+    autoLatestVersion: false,
   };
 
   constructor() {
diff --git a/assets/javascripts/models/doc.js b/assets/javascripts/models/doc.js
index 0a5c815a85..990c4046df 100644
--- a/assets/javascripts/models/doc.js
+++ b/assets/javascripts/models/doc.js
@@ -1,6 +1,8 @@
 app.models.Doc = class Doc extends app.Model {
   // Attributes: name, slug, type, version, release, db_size, mtime, links
 
+  static NUMBERED_VERSION_RGX = /^\d+(\.\d+)*$/;
+
   constructor() {
     super(...arguments);
     this.reset(this);
@@ -192,6 +194,53 @@ app.models.Doc = class Doc extends app.Model {
     );
   }
 
+  // Whether the doc holds a numbered version of its documentation (e.g. "3.9"),
+  // as opposed to a variant (e.g. "10 LTS" or "Python"), which can't be
+  // ordered. An empty version means the doc holds the latest version
+  // (e.g. `angular`), whereas docs without a version aren't versioned at all.
+  hasNumberedVersion() {
+    return (
+      this.version === "" || Doc.NUMBERED_VERSION_RGX.test(this.version || "")
+    );
+  }
+
+  // Compares numbered versions (e.g. "3.9" is older than "3.12").
+  // An empty version means the latest version and is newer than any other.
+  isNewerVersionThan(other) {
+    if (this.version === "" || other.version === "") {
+      return this.version === "" && other.version !== "";
+    }
+    const version = this.version.split(".");
+    const otherVersion = other.version.split(".");
+    for (let i = 0; i < Math.max(version.length, otherVersion.length); i++) {
+      const diff =
+        (parseInt(version[i], 10) || 0) - (parseInt(otherVersion[i], 10) || 0);
+      if (diff !== 0) {
+        return diff > 0;
+      }
+    }
+    return false;
+  }
+
+  // Returns the doc holding the latest version of the same documentation among
+  // `docs`, or the doc itself when there is none.
+  findLatestVersion(docs) {
+    let latest = this;
+    if (!this.hasNumberedVersion()) {
+      return latest;
+    }
+    for (var doc of docs) {
+      if (
+        doc.name === this.name &&
+        doc.hasNumberedVersion() &&
+        doc.isNewerVersionThan(latest)
+      ) {
+        latest = doc;
+      }
+    }
+    return latest;
+  }
+
   isOutdated(status) {
     if (!status) {
       return false;
diff --git a/assets/javascripts/templates/pages/settings_tmpl.js b/assets/javascripts/templates/pages/settings_tmpl.js
index cfd30de1b2..f0f84bfa19 100644
--- a/assets/javascripts/templates/pages/settings_tmpl.js
+++ b/assets/javascripts/templates/pages/settings_tmpl.js
@@ -60,6 +60,12 @@ app.templates.settingsPage = (settings) => `\
       }>Automatically download documentation for offline use
       <small>Only enable this when bandwidth isn't a concern to you.</small>
     </label>
+    <label class="_settings-label">
+      <input type="checkbox" form="settings" name="autoLatestVersion" value="_auto-latest-version"${
+        settings.autoLatestVersion ? " checked" : ""
+      }>Automatically switch to the latest version of a documentation
+      <small>With this checked, enabling e.g. CMake 3.9 switches to CMake 3.10 once it becomes available.</small>
+    </label>
     <label class="_settings-label _hide-in-development">
       <input type="checkbox" form="settings" name="analyticsConsent"${
         settings.analyticsConsent ? " checked" : ""
diff --git a/assets/javascripts/views/content/settings_page.js b/assets/javascripts/views/content/settings_page.js
index d8cee94889..fa68fecd90 100644
--- a/assets/javascripts/views/content/settings_page.js
+++ b/assets/javascripts/views/content/settings_page.js
@@ -17,6 +17,7 @@ app.views.SettingsPage = class SettingsPage extends app.View {
     settings.arrowScroll = app.settings.get("arrowScroll");
     settings.noAutofocus = app.settings.get("noAutofocus");
     settings.autoInstall = app.settings.get("autoInstall");
+    settings.autoLatestVersion = app.settings.get("autoLatestVersion");
     settings.analyticsConsent = app.settings.get("analyticsConsent");
     settings.spaceScroll = app.settings.get("spaceScroll");
     settings.spaceTimeout = app.settings.get("spaceTimeout");
diff --git a/test/assets/doc_version_test.js b/test/assets/doc_version_test.js
new file mode 100644
index 0000000000..448d815f16
--- /dev/null
+++ b/test/assets/doc_version_test.js
@@ -0,0 +1,172 @@
+const assert = require("node:assert/strict");
+const fs = require("node:fs");
+const test = require("node:test");
+const vm = require("node:vm");
+
+const context = {
+  $: {},
+  $$: {},
+  page: {},
+  window: { matchMedia: () => ({ media: "not all" }) },
+};
+
+vm.createContext(context);
+
+// The files are concatenated because top-level class declarations aren't
+// shared between scripts run in the same context.
+vm.runInContext(
+  [
+    "assets/javascripts/lib/events.js",
+    "assets/javascripts/app/app.js",
+    "assets/javascripts/models/model.js",
+    "assets/javascripts/models/doc.js",
+    "assets/javascripts/collections/collection.js",
+    "assets/javascripts/collections/docs.js",
+  ]
+    .map((file) => fs.readFileSync(file, "utf8"))
+    .join("\n"),
+  context,
+  { filename: "devdocs.js" },
+);
+
+const { app } = context;
+
+app.collections.Entries = class Entries {
+  each() {}
+};
+app.collections.Types = class Types {
+  each() {}
+};
+app.models.Entry = class Entry {
+  addAlias() {}
+};
+
+const CMAKE = [
+  { name: "CMake", slug: "cmake~3.12", version: "3.12" },
+  { name: "CMake", slug: "cmake~3.10", version: "3.10" },
+  { name: "CMake", slug: "cmake~3.9", version: "3.9" },
+];
+const NODE = [
+  { name: "Node.js", slug: "node", version: "" },
+  { name: "Node.js", slug: "node~10_lts", version: "10 LTS" },
+  { name: "Node.js", slug: "node~8_lts", version: "8 LTS" },
+];
+const BASH = [{ name: "Bash", slug: "bash" }];
+
+const newDoc = (attributes) => new app.models.Doc(attributes);
+const findLatest = (slug, attributes) => {
+  const docs = attributes.map(newDoc);
+  return docs.find((doc) => doc.slug === slug).findLatestVersion(docs).slug;
+};
+
+test("the latest version of a documentation compares versions numerically", () => {
+  assert.equal(findLatest("cmake~3.9", CMAKE), "cmake~3.12");
+  assert.equal(findLatest("cmake~3.12", CMAKE), "cmake~3.12");
+  assert.equal(
+    findLatest("bazel~9", [
+      { name: "Bazel", slug: "bazel~10", version: "10" },
+      { name: "Bazel", slug: "bazel~9", version: "9" },
+    ]),
+    "bazel~10",
+  );
+});
+
+test("a documentation without a version is the latest version", () => {
+  const docs = [
+    { name: "Angular", slug: "angular", version: "" },
+    { name: "Angular", slug: "angular~5", version: "5" },
+  ];
+  assert.equal(findLatest("angular~5", docs), "angular");
+  assert.equal(findLatest("angular", docs), "angular");
+});
+
+test("documentations that aren't versioned have no latest version", () => {
+  assert.equal(findLatest("bash", BASH), "bash");
+});
+
+test("variants of a documentation aren't versions", () => {
+  // Node.js 10 LTS isn't superseded by the unversioned (latest) Node.js doc,
+  // and neither is a Haxe target by the base Haxe doc.
+  assert.equal(findLatest("node~10_lts", NODE), "node~10_lts");
+  assert.equal(
+    findLatest("haxe~python", [
+      { name: "Haxe", slug: "haxe", version: "" },
+      { name: "Haxe", slug: "haxe~python", version: "Python" },
+    ]),
+    "haxe~python",
+  );
+});
+
+// The index of the latest version has to load for a doc to be replaced.
+app.models.Doc.prototype.load = function (onSuccess, onError) {
+  app.loads.push(this.slug);
+  if (app.loadFails) {
+    onError();
+  } else {
+    onSuccess();
+  }
+};
+
+const migrate = async (enabled, allDocs, autoLatestVersion = true) => {
+  app.settings = {
+    get: (key) => (key === "autoLatestVersion" ? autoLatestVersion : undefined),
+  };
+  app.docs = new app.collections.Docs();
+  app.disabledDocs = new app.collections.Docs();
+  for (const attributes of allDocs) {
+    (enabled.includes(attributes.slug) ? app.docs : app.disabledDocs).add(
+      attributes,
+    );
+  }
+  app.saveDocs = () => {
+    app.saved = true;
+  };
+  app.saved = false;
+  app.loads = [];
+  await app.migrateToLatestVersions();
+  // Spread the array so that it's created in this realm, not the VM's.
+  return [...app.docs.all().map((doc) => doc.slug)];
+};
+
+test("enabled docs are migrated to their latest version at boot", async () => {
+  assert.deepEqual(await migrate(["cmake~3.9", "bash"], [...CMAKE, ...BASH]), [
+    "bash",
+    "cmake~3.12",
+  ]);
+  assert.equal(app.saved, true);
+  assert.equal(app.disabledDocs.findBy("slug", "cmake~3.9").slug, "cmake~3.9");
+});
+
+test("outdated docs are disabled when their latest version is already enabled", async () => {
+  assert.deepEqual(await migrate(["cmake~3.9", "cmake~3.12"], CMAKE), [
+    "cmake~3.12",
+  ]);
+});
+
+test("the version superseding several docs is only loaded once", async () => {
+  assert.deepEqual(await migrate(["cmake~3.9", "cmake~3.10"], CMAKE), [
+    "cmake~3.12",
+  ]);
+  assert.deepEqual([...app.loads], ["cmake~3.12"]);
+});
+
+test("a doc whose latest version fails to load isn't replaced", async () => {
+  app.loadFails = true;
+  try {
+    assert.deepEqual(await migrate(["cmake~3.9"], CMAKE), ["cmake~3.9"]);
+    assert.equal(app.saved, false);
+  } finally {
+    app.loadFails = false;
+  }
+});
+
+test("docs are left alone without the preference or a newer version", async () => {
+  assert.deepEqual(await migrate(["cmake~3.9"], CMAKE, false), ["cmake~3.9"]);
+  assert.equal(app.saved, false);
+
+  assert.deepEqual(
+    await migrate(["cmake~3.12", "node~10_lts"], [...CMAKE, ...NODE]),
+    ["cmake~3.12", "node~10_lts"],
+  );
+  assert.equal(app.saved, false);
+});