diff --git a/app/assets/javascripts/discourse/app/instance-initializers/url-redirects.js b/app/assets/javascripts/discourse/app/instance-initializers/url-redirects.js
index a90b9eb6c94..80bba7ca945 100644
--- a/app/assets/javascripts/discourse/app/instance-initializers/url-redirects.js
+++ b/app/assets/javascripts/discourse/app/instance-initializers/url-redirects.js
@@ -10,8 +10,16 @@ export default {
     DiscourseURL.rewrite(/^\/groups$/, "/g");
     DiscourseURL.rewrite(/^\/groups\//, "/g/");
 
-    // Initialize default homepage
+    const currentUser = owner.lookup("service:current-user");
     let siteSettings = owner.lookup("service:site-settings");
+
+    // Setup `/my` redirects
+    if (currentUser) {
+      DiscourseURL.rewrite(/^\/my\//, `/u/${currentUser.username_lower}/`);
+    } else {
+      DiscourseURL.rewrite(/^\/my\/.*/, "/login-preferences");
+    }
+
     initializeDefaultHomepage(siteSettings);
   },
 };
diff --git a/app/assets/javascripts/discourse/app/lib/url.js b/app/assets/javascripts/discourse/app/lib/url.js
index 34816737966..c9c21ebac68 100644
--- a/app/assets/javascripts/discourse/app/lib/url.js
+++ b/app/assets/javascripts/discourse/app/lib/url.js
@@ -8,7 +8,6 @@ import offsetCalculator from "discourse/lib/offset-calculator";
 import { defaultHomepage } from "discourse/lib/utilities";
 import Category from "discourse/models/category";
 import Session from "discourse/models/session";
-import User from "discourse/models/user";
 import { isTesting } from "discourse-common/config/environment";
 import getURL, { withoutPrefix } from "discourse-common/lib/get-url";
 
@@ -227,21 +226,6 @@ const DiscourseURL = EmberObject.extend({
 
     path = path.replace(/(https?\:)?\/\/[^\/]+/, "");
 
-    // Rewrite /my/* urls
-    let myPath = getURL("/my/");
-    const fullPath = getURL(path);
-    if (fullPath.startsWith(myPath)) {
-      const currentUser = User.current();
-      if (currentUser) {
-        path = fullPath.replace(
-          myPath,
-          `${userPath(currentUser.get("username_lower"))}/`
-        );
-      } else {
-        return this.redirectTo("/login-preferences");
-      }
-    }
-
     // handle prefixes
     if (path.startsWith("/")) {
       path = withoutPrefix(path);
diff --git a/app/assets/javascripts/discourse/tests/acceptance/group-index-test.js b/app/assets/javascripts/discourse/tests/acceptance/group-index-test.js
index 389afa2c1a0..d89d1cc9eb2 100644
--- a/app/assets/javascripts/discourse/tests/acceptance/group-index-test.js
+++ b/app/assets/javascripts/discourse/tests/acceptance/group-index-test.js
@@ -1,4 +1,4 @@
-import { click, currentURL, visit } from "@ember/test-helpers";
+import { click, currentURL, settled, visit } from "@ember/test-helpers";
 import { test } from "qunit";
 import {
   acceptance,
@@ -146,6 +146,9 @@ acceptance("Group Members", function (needs) {
   });
 });
 
+/**
+ * Workaround for https://github.com/tildeio/router.js/pull/335
+ */
 async function visitWithRedirects(url) {
   try {
     await visit(url);
@@ -154,6 +157,7 @@ async function visitWithRedirects(url) {
     if (message !== "TransitionAborted") {
       throw error;
     }
+    await settled();
   }
 }
 
diff --git a/app/assets/javascripts/discourse/tests/acceptance/user-test.js b/app/assets/javascripts/discourse/tests/acceptance/user-test.js
index 20f67acc58c..4d28c77012b 100644
--- a/app/assets/javascripts/discourse/tests/acceptance/user-test.js
+++ b/app/assets/javascripts/discourse/tests/acceptance/user-test.js
@@ -1,5 +1,11 @@
 import EmberObject from "@ember/object";
-import { click, currentRouteName, visit } from "@ember/test-helpers";
+import {
+  click,
+  currentRouteName,
+  currentURL,
+  settled,
+  visit,
+} from "@ember/test-helpers";
 import { test } from "qunit";
 import userFixtures from "discourse/tests/fixtures/user-fixtures";
 import {
@@ -14,6 +20,21 @@ import selectKit from "discourse/tests/helpers/select-kit-helper";
 import { cloneJSON } from "discourse-common/lib/object";
 import I18n from "discourse-i18n";
 
+/**
+ * Workaround for https://github.com/tildeio/router.js/pull/335
+ */
+async function visitWithRedirects(url) {
+  try {
+    await visit(url);
+  } catch (error) {
+    const { message } = error;
+    if (message !== "TransitionAborted") {
+      throw error;
+    }
+    await settled();
+  }
+}
+
 acceptance("User Routes", function (needs) {
   needs.user();
 
@@ -386,3 +407,25 @@ acceptance("User - Logout", function (needs) {
     await click(".dialog-overlay");
   });
 });
+
+acceptance("User - /my/ shortcuts for logged-in users", function (needs) {
+  needs.user({ username: "eviltrout" });
+
+  test("Redirects correctly", async function (assert) {
+    await visitWithRedirects("/my/activity");
+    assert.strictEqual(currentURL(), "/u/eviltrout/activity");
+
+    await visitWithRedirects("/my/preferences/account");
+    assert.strictEqual(currentURL(), "/u/eviltrout/preferences/account");
+  });
+});
+
+acceptance("User - /my/ shortcuts for anon users", function () {
+  test("Redirects correctly", async function (assert) {
+    await visitWithRedirects("/my/activity");
+    assert.strictEqual(currentURL(), "/login-preferences");
+
+    await visitWithRedirects("/my/preferences/account");
+    assert.strictEqual(currentURL(), "/login-preferences");
+  });
+});
diff --git a/app/assets/javascripts/discourse/tests/unit/lib/url-test.js b/app/assets/javascripts/discourse/tests/unit/lib/url-test.js
index 81c6f570f21..387caf2b30d 100644
--- a/app/assets/javascripts/discourse/tests/unit/lib/url-test.js
+++ b/app/assets/javascripts/discourse/tests/unit/lib/url-test.js
@@ -6,7 +6,6 @@ import DiscourseURL, {
   prefixProtocol,
   userPath,
 } from "discourse/lib/url";
-import User from "discourse/models/user";
 import { logIn } from "discourse/tests/helpers/qunit-helpers";
 import { setPrefix } from "discourse-common/lib/get-url";
 
@@ -77,8 +76,6 @@ module("Unit | Utility | url", function (hooks) {
 
   test("routeTo with prefix", async function (assert) {
     setPrefix("/forum");
-    logIn();
-    const user = User.current();
 
     sinon.stub(DiscourseURL, "router").get(() => {
       return {
@@ -88,7 +85,7 @@ module("Unit | Utility | url", function (hooks) {
     sinon.stub(DiscourseURL, "handleURL");
     DiscourseURL.routeTo("/my/messages");
     assert.ok(
-      DiscourseURL.handleURL.calledWith(`/u/${user.username}/messages`),
+      DiscourseURL.handleURL.calledWith(`/my/messages`),
       "it should navigate to the messages page"
     );
   });