diff --git a/server/models/Collection.js b/server/models/Collection.js
index 039420c50..5b152df2f 100644
--- a/server/models/Collection.js
+++ b/server/models/Collection.js
@@ -7,6 +7,7 @@ import { Op, DataTypes, sequelize } from "../sequelize";
 import slugify from "../utils/slugify";
 import CollectionUser from "./CollectionUser";
 import Document from "./Document";
+import User from "./User";
 
 const Collection = sequelize.define(
   "collection",
@@ -236,6 +237,25 @@ Collection.findByPk = async function (id, options = {}) {
   }
 };
 
+/**
+ * Find the first collection that the specified user has access to.
+ *
+ * @param user User object
+ * @returns collection First collection in the sidebar order
+ */
+Collection.findFirstCollectionForUser = async (user: User) => {
+  const id = await user.collectionIds();
+
+  return Collection.findOne({
+    where: { id },
+    order: [
+      // using LC_COLLATE:"C" because we need byte order to drive the sorting
+      sequelize.literal('"collection"."index" collate "C"'),
+      ["updatedAt", "DESC"],
+    ],
+  });
+};
+
 // get all the membership relationshps a user could have with the collection
 Collection.membershipUserIds = async (collectionId: string) => {
   const collection = await Collection.scope("withAllMemberships").findByPk(
diff --git a/server/routes/auth/index.js b/server/routes/auth/index.js
index 5974340de..3fcfb3d59 100644
--- a/server/routes/auth/index.js
+++ b/server/routes/auth/index.js
@@ -43,10 +43,7 @@ router.get("/redirect", auth(), async (ctx) => {
 
   const [team, collection, view] = await Promise.all([
     Team.findByPk(user.teamId),
-    Collection.findOne({
-      where: { teamId: user.teamId },
-      order: [["index", "ASC"]],
-    }),
+    Collection.findFirstCollectionForUser(user),
     View.findOne({
       where: { userId: user.id },
     }),
diff --git a/server/routes/auth/index.test.js b/server/routes/auth/index.test.js
new file mode 100644
index 000000000..76590520e
--- /dev/null
+++ b/server/routes/auth/index.test.js
@@ -0,0 +1,36 @@
+// @flow
+import TestServer from "fetch-test-server";
+import webService from "../../services/web";
+import { buildUser, buildCollection } from "../../test/factories";
+import { flushdb } from "../../test/support";
+
+const app = webService();
+const server = new TestServer(app.callback());
+
+beforeEach(() => flushdb());
+afterAll(() => server.close());
+
+describe("auth/redirect", () => {
+  it("should redirect to home", async () => {
+    const user = await buildUser();
+    const res = await server.get(
+      `/auth/redirect?token=${user.getTransferToken()}`,
+      { redirect: "manual" }
+    );
+
+    expect(res.status).toEqual(302);
+    expect(res.headers.get("location").endsWith("/home")).toBeTruthy();
+  });
+
+  it("should redirect to first collection", async () => {
+    const collection = await buildCollection();
+    const user = await buildUser({ teamId: collection.teamId });
+    const res = await server.get(
+      `/auth/redirect?token=${user.getTransferToken()}`,
+      { redirect: "manual" }
+    );
+
+    expect(res.status).toEqual(302);
+    expect(res.headers.get("location").endsWith(collection.url)).toBeTruthy();
+  });
+});
diff --git a/server/utils/authentication.js b/server/utils/authentication.js
index 66b1b85d3..230eb6896 100644
--- a/server/utils/authentication.js
+++ b/server/utils/authentication.js
@@ -101,10 +101,7 @@ export async function signIn(
     });
 
     const [collection, view] = await Promise.all([
-      Collection.findOne({
-        where: { teamId: user.teamId },
-        order: [["index", "ASC"]],
-      }),
+      Collection.findFirstCollectionForUser(user),
       View.findOne({
         where: { userId: user.id },
       }),