diff --git a/cypress/e2e/permalinks/permalinks.spec.ts b/cypress/e2e/permalinks/permalinks.spec.ts
new file mode 100644
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+++ b/cypress/e2e/permalinks/permalinks.spec.ts
@@ -0,0 +1,136 @@
+/*
+Copyright 2023 The Matrix.org Foundation C.I.C.
+
+Licensed under the Apache License, Version 2.0 (the "License");
+you may not use this file except in compliance with the License.
+You may obtain a copy of the License at
+
+    http://www.apache.org/licenses/LICENSE-2.0
+
+Unless required by applicable law or agreed to in writing, software
+distributed under the License is distributed on an "AS IS" BASIS,
+WITHOUT WARRANTIES OR CONDITIONS OF ANY KIND, either express or implied.
+See the License for the specific language governing permissions and
+limitations under the License.
+*/
+
+import { ISendEventResponse } from "matrix-js-sdk/src/matrix";
+
+import { HomeserverInstance } from "../../plugins/utils/homeserver";
+import type { CypressBot } from "../../support/bot";
+
+const room1Name = "Room 1";
+const room2Name = "Room 2";
+const unknownRoomAlias = "#unknownroom:example.com";
+const permalinkPrefix = "https://matrix.to/#/";
+
+const getPill = (label: string) => {
+    return cy.contains(".mx_Pill_text", new RegExp("^" + label + "$", "g"));
+};
+
+describe("permalinks", () => {
+    beforeEach(() => {
+        cy.startHomeserver("default")
+            .as("homeserver")
+            .then((homeserver: HomeserverInstance) => {
+                cy.initTestUser(homeserver, "Alice");
+
+                cy.createRoom({ name: room1Name }).as("room1Id");
+                cy.createRoom({ name: room2Name }).as("room2Id");
+
+                cy.getBot(homeserver, { displayName: "Bob" }).as("bob");
+                cy.getBot(homeserver, { displayName: "Charlotte" }).as("charlotte");
+                cy.getBot(homeserver, { displayName: "Danielle" }).as("danielle");
+            });
+    });
+
+    afterEach(() => {
+        cy.get<HomeserverInstance>("@homeserver").then((homeserver: HomeserverInstance) => {
+            cy.stopHomeserver(homeserver);
+        });
+    });
+
+    it("shoud render permalinks as expected", () => {
+        let danielle: CypressBot;
+
+        cy.get<CypressBot>("@danielle").then((d) => {
+            danielle = d;
+        });
+
+        cy.viewRoomByName(room1Name);
+
+        cy.all([
+            cy.getClient(),
+            cy.get<string>("@room1Id"),
+            cy.get<string>("@room2Id"),
+            cy.get<CypressBot>("@bob"),
+            cy.get<CypressBot>("@charlotte"),
+        ]).then(([client, room1Id, room2Id, bob, charlotte]) => {
+            cy.inviteUser(room1Id, bob.getUserId());
+            cy.botJoinRoom(bob, room1Id);
+            cy.inviteUser(room2Id, charlotte.getUserId());
+            cy.botJoinRoom(charlotte, room2Id);
+
+            cy.botSendMessage(client, room1Id, "At room mention: @room");
+
+            cy.botSendMessage(client, room1Id, `Permalink to Room 2: ${permalinkPrefix}${room2Id}`);
+            cy.botSendMessage(
+                client,
+                room1Id,
+                `Permalink to an unknown room alias: ${permalinkPrefix}${unknownRoomAlias}`,
+            );
+
+            cy.botSendMessage(bob, room1Id, "Hello").then((result: ISendEventResponse) => {
+                cy.botSendMessage(
+                    client,
+                    room1Id,
+                    `Permalink to a message in the same room: ${permalinkPrefix}${room1Id}/${result.event_id}`,
+                );
+            });
+            cy.botSendMessage(charlotte, room2Id, "Hello").then((result: ISendEventResponse) => {
+                cy.botSendMessage(
+                    client,
+                    room1Id,
+                    `Permalink to a message in another room: ${permalinkPrefix}${room2Id}/${result.event_id}`,
+                );
+            });
+            cy.botSendMessage(client, room1Id, `Permalink to an uknonwn message: ${permalinkPrefix}${room1Id}/$abc123`);
+
+            cy.botSendMessage(client, room1Id, `Permalink to a user in the room: ${permalinkPrefix}${bob.getUserId()}`);
+            cy.botSendMessage(
+                client,
+                room1Id,
+                `Permalink to a user in another room: ${permalinkPrefix}${charlotte.getUserId()}`,
+            );
+            cy.botSendMessage(
+                client,
+                room1Id,
+                `Permalink to a user with whom alice doesn't share a room: ${permalinkPrefix}${danielle.getUserId()}`,
+            );
+        });
+
+        cy.get(".mx_RoomView_timeline").within(() => {
+            getPill("@room");
+
+            getPill(room2Name);
+            getPill(unknownRoomAlias);
+
+            getPill("Message from Bob");
+            getPill(`Message in ${room2Name}`);
+            getPill("Message");
+
+            getPill("Bob");
+            getPill("Charlotte");
+            // This is the permalink to Danielle's profile. It should only display the MXID
+            // because the profile is unknown (not sharing any room with Danielle).
+            getPill(danielle.getSafeUserId());
+        });
+
+        // clean up before taking the snapshot
+        cy.get(".mx_cryptoEvent").invoke("remove");
+        cy.get(".mx_NewRoomIntro").invoke("remove");
+        cy.get(".mx_GenericEventListSummary").invoke("remove");
+
+        cy.get(".mx_RoomView_timeline").percySnapshotElement("Permalink rendering");
+    });
+});