diff --git a/cypress/integration/10-user-view/user-view.spec.ts b/cypress/integration/10-user-view/user-view.spec.ts
index e98a1d47f4..30c3ff23ca 100644
--- a/cypress/integration/10-user-view/user-view.spec.ts
+++ b/cypress/integration/10-user-view/user-view.spec.ts
@@ -27,7 +27,7 @@ describe("UserView", () => {
             synapse = data;
 
             cy.initTestUser(synapse, "Violet");
-            cy.getBot(synapse, "Usman").as("bot");
+            cy.getBot(synapse, { displayName: "Usman" }).as("bot");
         });
     });
 
diff --git a/cypress/integration/11-room-directory/room-directory.spec.ts b/cypress/integration/11-room-directory/room-directory.spec.ts
index e7e3c5c9c8..18464e2071 100644
--- a/cypress/integration/11-room-directory/room-directory.spec.ts
+++ b/cypress/integration/11-room-directory/room-directory.spec.ts
@@ -27,7 +27,7 @@ describe("Room Directory", () => {
             synapse = data;
 
             cy.initTestUser(synapse, "Ray");
-            cy.getBot(synapse, "Paul").as("bot");
+            cy.getBot(synapse, { displayName: "Paul" }).as("bot");
         });
     });
 
diff --git a/cypress/integration/12-spotlight/spotlight.spec.ts b/cypress/integration/12-spotlight/spotlight.spec.ts
index 5c0018b499..5a76d17b4c 100644
--- a/cypress/integration/12-spotlight/spotlight.spec.ts
+++ b/cypress/integration/12-spotlight/spotlight.spec.ts
@@ -128,11 +128,11 @@ describe("Spotlight", () => {
         cy.startSynapse("default").then(data => {
             synapse = data;
             cy.initTestUser(synapse, "Jim").then(() =>
-                cy.getBot(synapse, bot1Name).then(_bot1 => {
+                cy.getBot(synapse, { displayName: bot1Name }).then(_bot1 => {
                     bot1 = _bot1;
                 }),
             ).then(() =>
-                cy.getBot(synapse, bot2Name).then(_bot2 => {
+                cy.getBot(synapse, { displayName: bot2Name }).then(_bot2 => {
                     // eslint-disable-next-line @typescript-eslint/no-unused-vars
                     bot2 = _bot2;
                 }),
diff --git a/cypress/integration/5-threads/threads.spec.ts b/cypress/integration/5-threads/threads.spec.ts
index 64269b1457..3decae3876 100644
--- a/cypress/integration/5-threads/threads.spec.ts
+++ b/cypress/integration/5-threads/threads.spec.ts
@@ -73,7 +73,7 @@ describe("Threads", () => {
 
     it("should be usable for a conversation", () => {
         let bot: MatrixClient;
-        cy.getBot(synapse, "BotBob").then(_bot => {
+        cy.getBot(synapse, { displayName: "BotBob" }).then(_bot => {
             bot = _bot;
         });
 
diff --git a/cypress/integration/6-spaces/spaces.spec.ts b/cypress/integration/6-spaces/spaces.spec.ts
index e5c03229bf..8adfb34c51 100644
--- a/cypress/integration/6-spaces/spaces.spec.ts
+++ b/cypress/integration/6-spaces/spaces.spec.ts
@@ -167,7 +167,7 @@ describe("Spaces", () => {
 
     it("should allow user to invite another to a space", () => {
         let bot: MatrixClient;
-        cy.getBot(synapse, "BotBob").then(_bot => {
+        cy.getBot(synapse, { displayName: "BotBob" }).then(_bot => {
             bot = _bot;
         });
 
@@ -202,7 +202,7 @@ describe("Spaces", () => {
         });
         getSpacePanelButton("My Space").should("exist");
 
-        cy.getBot(synapse, "BotBob").then({ timeout: 10000 }, async bot => {
+        cy.getBot(synapse, { displayName: "BotBob" }).then({ timeout: 10000 }, async bot => {
             const { room_id: roomId } = await bot.createRoom(spaceCreateOptions("Space Space"));
             await bot.invite(roomId, user.userId);
         });
diff --git a/cypress/integration/7-crypto/crypto.spec.ts b/cypress/integration/7-crypto/crypto.spec.ts
index 6f1f7aa6c8..020ca08bd3 100644
--- a/cypress/integration/7-crypto/crypto.spec.ts
+++ b/cypress/integration/7-crypto/crypto.spec.ts
@@ -14,73 +14,145 @@ See the License for the specific language governing permissions and
 limitations under the License.
 */
 
-/// <reference types="cypress" />
-
-import type { MatrixClient } from "matrix-js-sdk/src/matrix";
+import type { VerificationRequest } from "matrix-js-sdk/src/crypto/verification/request/VerificationRequest";
+import type { ISasEvent } from "matrix-js-sdk/src/crypto/verification/SAS";
+import type { MatrixClient, Room } from "matrix-js-sdk/src/matrix";
 import { SynapseInstance } from "../../plugins/synapsedocker";
+import Chainable = Cypress.Chainable;
 
-function waitForEncryption(cli: MatrixClient, roomId: string, win: Cypress.AUTWindow): Promise<void> {
-    return new Promise<void>(resolve => {
-        const onEvent = () => {
-            cli.crypto.cryptoStore.getEndToEndRooms(null, (result) => {
-                if (result[roomId]) {
-                    cli.off(win.matrixcs.ClientEvent.Event, onEvent);
-                    resolve();
-                }
-            });
-        };
-        cli.on(win.matrixcs.ClientEvent.Event, onEvent);
-    });
+type EmojiMapping = [emoji: string, name: string];
+interface CryptoTestContext extends Mocha.Context {
+    synapse: SynapseInstance;
+    bob: MatrixClient;
 }
 
-describe("Cryptography", () => {
-    beforeEach(() => {
-        cy.startSynapse("default").as('synapse').then(
-            synapse => cy.initTestUser(synapse, "Alice"),
-        );
+const waitForVerificationRequest = (cli: MatrixClient): Promise<VerificationRequest> => {
+    return new Promise<VerificationRequest>(resolve => {
+        const onVerificationRequestEvent = (request: VerificationRequest) => {
+            // @ts-ignore CryptoEvent is not exported to window.matrixcs; using the string value here
+            cli.off("crypto.verification.request", onVerificationRequestEvent);
+            resolve(request);
+        };
+        // @ts-ignore
+        cli.on("crypto.verification.request", onVerificationRequestEvent);
     });
+};
 
-    afterEach(() => {
-        cy.get<SynapseInstance>('@synapse').then(synapse => cy.stopSynapse(synapse));
+const openRoomInfo = () => {
+    cy.get(".mx_RightPanel_roomSummaryButton").click();
+    return cy.get(".mx_RightPanel");
+};
+
+const checkDMRoom = () => {
+    cy.contains(".mx_TextualEvent", "Alice invited Bob").should("exist");
+    cy.contains(".mx_RoomView_body .mx_cryptoEvent", "Encryption enabled").should("exist");
+};
+
+const startDMWithBob = function(this: CryptoTestContext) {
+    cy.get('.mx_RoomList [aria-label="Start chat"]').click();
+    cy.get('[data-test-id="invite-dialog-input"]').type(this.bob.getUserId());
+    cy.contains(".mx_InviteDialog_tile_nameStack_name", "Bob").click();
+    cy.contains(".mx_InviteDialog_userTile_pill .mx_InviteDialog_userTile_name", "Bob").should("exist");
+    cy.get(".mx_InviteDialog_goButton").click();
+};
+
+const testMessages = function(this: CryptoTestContext) {
+    cy.get(".mx_BasicMessageComposer_input").should("have.focus").type("Hey!{enter}");
+    cy.contains(".mx_EventTile_body", "Hey!")
+        .closest(".mx_EventTile")
+        .should("not.have.descendants", ".mx_EventTile_e2eIcon_warning")
+        .should("have.descendants", ".mx_EventTile_receiptSent");
+
+    // Bob sends a response
+    cy.get<Room>("@bobsRoom").then((room) => {
+        this.bob.sendTextMessage(room.roomId, "Hoo!");
     });
+    cy.contains(".mx_EventTile_body", "Hoo!")
+        .closest(".mx_EventTile")
+        .should("not.have.descendants", ".mx_EventTile_e2eIcon_warning");
+};
 
-    it("should receive and decrypt encrypted messages", () => {
-        cy.get<SynapseInstance>('@synapse').then(synapse => cy.getBot(synapse, "Beatrice").as('bot'));
+const bobJoin = function(this: CryptoTestContext) {
+    cy.botJoinRoomByName(this.bob, "Alice").as("bobsRoom");
+    cy.contains(".mx_TextualEvent", "Bob joined the room").should("exist");
+};
 
-        cy.createRoom({
-            initial_state: [
-                {
-                    type: "m.room.encryption",
-                    state_key: '',
-                    content: {
-                        algorithm: "m.megolm.v1.aes-sha2",
-                    },
-                },
-            ],
-        }).as('roomId');
+const handleVerificationRequest = (request: VerificationRequest): Chainable<EmojiMapping[]> => {
+    return cy.wrap(new Promise<EmojiMapping[]>((resolve) => {
+        const onShowSas = (event: ISasEvent) => {
+            resolve(event.sas.emoji);
+            verifier.off("show_sas", onShowSas);
+            event.confirm();
+            verifier.done();
+        };
 
-        cy.all([
-            cy.get<MatrixClient>('@bot'),
-            cy.get<string>('@roomId'),
-            cy.window(),
-        ]).then(([bot, roomId, win]) => {
-            cy.inviteUser(roomId, bot.getUserId());
-            cy.wrap(
-                waitForEncryption(
-                    bot, roomId, win,
-                ).then(() => bot.sendMessage(roomId, {
-                    body: "Top secret message",
-                    msgtype: "m.text",
-                })),
-            );
-            cy.visit("/#/room/" + roomId);
+        const verifier = request.beginKeyVerification("m.sas.v1");
+        verifier.on("show_sas", onShowSas);
+        verifier.verify();
+    }));
+};
+
+const verify = function(this: CryptoTestContext) {
+    const bobsVerificationRequestPromise = waitForVerificationRequest(this.bob);
+
+    openRoomInfo().within(() => {
+        cy.get(".mx_RoomSummaryCard_icon_people").click();
+        cy.contains(".mx_EntityTile_name", "Bob").click();
+        cy.contains(".mx_UserInfo_verifyButton", "Verify").click();
+        cy.contains(".mx_AccessibleButton", "Start Verification").click();
+        cy.wrap(bobsVerificationRequestPromise).then((verificationRequest: VerificationRequest) => {
+            verificationRequest.accept();
+            return verificationRequest;
+        }).as("bobsVerificationRequest");
+        cy.contains(".mx_AccessibleButton", "Verify by emoji").click();
+        cy.get<VerificationRequest>("@bobsVerificationRequest").then((request: VerificationRequest) => {
+            return handleVerificationRequest(request).then((emojis: EmojiMapping[]) => {
+                cy.get('.mx_VerificationShowSas_emojiSas_block').then((emojiBlocks) => {
+                    emojis.forEach((emoji: EmojiMapping, index: number) => {
+                        expect(emojiBlocks[index].textContent.toLowerCase()).to.eq(emoji[0] + emoji[1]);
+                    });
+                });
+            });
         });
+        cy.contains(".mx_AccessibleButton", "They match").click();
+        cy.contains("You've successfully verified Bob!").should("exist");
+        cy.contains(".mx_AccessibleButton", "Got it").click();
+    });
+};
 
-        cy.get(".mx_RoomView_body .mx_cryptoEvent").should("contain", "Encryption enabled");
+describe("Cryptography", function() {
+    beforeEach(function() {
+        cy.startSynapse("default").as("synapse").then((synapse: SynapseInstance) => {
+            cy.initTestUser(synapse, "Alice");
+            cy.getBot(synapse, { displayName: "Bob", autoAcceptInvites: false }).as("bob");
+        });
+    });
 
-        cy.get(".mx_EventTile_body")
-            .contains("Top secret message")
-            .closest(".mx_EventTile_line")
-            .should("not.have.descendants", ".mx_EventTile_e2eIcon_warning");
+    afterEach(function(this: CryptoTestContext) {
+        cy.stopSynapse(this.synapse);
+    });
+
+    it("setting up secure key backup should work", () => {
+        cy.openUserSettings("Security & Privacy");
+        cy.contains(".mx_AccessibleButton", "Set up Secure Backup").click();
+        cy.get(".mx_Dialog").within(() => {
+            cy.contains(".mx_Dialog_primary", "Continue").click();
+            cy.get(".mx_CreateSecretStorageDialog_recoveryKey code").invoke("text").as("securityKey");
+            // Clicking download instead of Copy because of https://github.com/cypress-io/cypress/issues/2851
+            cy.contains(".mx_AccessibleButton", "Download").click();
+            cy.contains(".mx_Dialog_primary:not([disabled])", "Continue").click();
+            cy.contains(".mx_Dialog_title", "Setting up keys").should("exist");
+            cy.contains(".mx_Dialog_title", "Setting up keys").should("not.exist");
+        });
+        return;
+    });
+
+    it("creating a DM should work, being e2e-encrypted / user verification", function(this: CryptoTestContext) {
+        cy.bootstrapCrossSigning();
+        startDMWithBob.call(this);
+        checkDMRoom();
+        bobJoin.call(this);
+        testMessages.call(this);
+        verify.call(this);
     });
 });
diff --git a/cypress/plugins/synapsedocker/templates/default/homeserver.yaml b/cypress/plugins/synapsedocker/templates/default/homeserver.yaml
index 7839c69c46..842009bcae 100644
--- a/cypress/plugins/synapsedocker/templates/default/homeserver.yaml
+++ b/cypress/plugins/synapsedocker/templates/default/homeserver.yaml
@@ -50,3 +50,6 @@ signing_key_path: "/data/localhost.signing.key"
 trusted_key_servers:
   - server_name: "matrix.org"
 suppress_key_server_warning: true
+
+ui_auth:
+  session_timeout: "300s"
diff --git a/cypress/support/bot.ts b/cypress/support/bot.ts
index b75633d27d..91efca9ea0 100644
--- a/cypress/support/bot.ts
+++ b/cypress/support/bot.ts
@@ -18,10 +18,25 @@ limitations under the License.
 
 import request from "browser-request";
 
-import type { MatrixClient } from "matrix-js-sdk/src/client";
+import type { MatrixClient, Room } from "matrix-js-sdk/src/matrix";
 import { SynapseInstance } from "../plugins/synapsedocker";
 import Chainable = Cypress.Chainable;
 
+interface CreateBotOpts {
+    /**
+     * Whether the bot should automatically accept all invites.
+     */
+    autoAcceptInvites?: boolean;
+    /**
+     * The display name to give to that bot user
+     */
+    displayName?: string;
+}
+
+const defaultCreateBotOptions = {
+    autoAcceptInvites: true,
+} as CreateBotOpts;
+
 declare global {
     // eslint-disable-next-line @typescript-eslint/no-namespace
     namespace Cypress {
@@ -29,17 +44,30 @@ declare global {
             /**
              * Returns a new Bot instance
              * @param synapse the instance on which to register the bot user
-             * @param displayName the display name to give to the bot user
+             * @param opts create bot options
              */
-            getBot(synapse: SynapseInstance, displayName?: string): Chainable<MatrixClient>;
+            getBot(synapse: SynapseInstance, opts: CreateBotOpts): Chainable<MatrixClient>;
+            /**
+             * Let a bot join a room
+             * @param cli The bot's MatrixClient
+             * @param roomId ID of the room to join
+             */
+            botJoinRoom(cli: MatrixClient, roomId: string): Chainable<Room>;
+            /**
+             * Let a bot join a room by name
+             * @param cli The bot's MatrixClient
+             * @param roomName Name of the room to join
+             */
+            botJoinRoomByName(cli: MatrixClient, roomName: string): Chainable<Room>;
         }
     }
 }
 
-Cypress.Commands.add("getBot", (synapse: SynapseInstance, displayName?: string): Chainable<MatrixClient> => {
+Cypress.Commands.add("getBot", (synapse: SynapseInstance, opts: CreateBotOpts): Chainable<MatrixClient> => {
+    opts = Object.assign({}, defaultCreateBotOptions, opts);
     const username = Cypress._.uniqueId("userId_");
     const password = Cypress._.uniqueId("password_");
-    return cy.registerUser(synapse, username, password, displayName).then(credentials => {
+    return cy.registerUser(synapse, username, password, opts.displayName).then(credentials => {
         return cy.window({ log: false }).then(win => {
             const cli = new win.matrixcs.MatrixClient({
                 baseUrl: synapse.baseUrl,
@@ -52,18 +80,37 @@ Cypress.Commands.add("getBot", (synapse: SynapseInstance, displayName?: string):
                 cryptoStore: new win.matrixcs.MemoryCryptoStore(),
             });
 
-            cli.on(win.matrixcs.RoomMemberEvent.Membership, (event, member) => {
-                if (member.membership === "invite" && member.userId === cli.getUserId()) {
-                    cli.joinRoom(member.roomId);
-                }
-            });
+            if (opts.autoAcceptInvites) {
+                cli.on(win.matrixcs.RoomMemberEvent.Membership, (event, member) => {
+                    if (member.membership === "invite" && member.userId === cli.getUserId()) {
+                        cli.joinRoom(member.roomId);
+                    }
+                });
+            }
 
             return cy.wrap(
                 cli.initCrypto()
                     .then(() => cli.setGlobalErrorOnUnknownDevices(false))
                     .then(() => cli.startClient())
+                    .then(() => cli.bootstrapCrossSigning({
+                        authUploadDeviceSigningKeys: async func => { await func({}); },
+                    }))
                     .then(() => cli),
             );
         });
     });
 });
+
+Cypress.Commands.add("botJoinRoom", (cli: MatrixClient, roomId: string): Chainable<Room> => {
+    return cy.wrap(cli.joinRoom(roomId));
+});
+
+Cypress.Commands.add("botJoinRoomByName", (cli: MatrixClient, roomName: string): Chainable<Room> => {
+    const room = cli.getRooms().find((r) => r.getDefaultRoomName(cli.getUserId()) === roomName);
+
+    if (room) {
+        return cy.botJoinRoom(cli, room.roomId);
+    }
+
+    return cy.wrap(Promise.reject());
+});
diff --git a/cypress/support/client.ts b/cypress/support/client.ts
index db27f4d2b1..bd3f6d1514 100644
--- a/cypress/support/client.ts
+++ b/cypress/support/client.ts
@@ -53,6 +53,10 @@ declare global {
              * @param data The data to store.
              */
             setAccountData(type: string, data: object): Chainable<{}>;
+            /**
+             * Boostraps cross-signing.
+             */
+            bootstrapCrossSigning(): Chainable<void>;
         }
     }
 }
@@ -103,3 +107,11 @@ Cypress.Commands.add("setAccountData", (type: string, data: object): Chainable<{
         return cli.setAccountData(type, data);
     });
 });
+
+Cypress.Commands.add("bootstrapCrossSigning", () => {
+    cy.window({ log: false }).then(win => {
+        win.mxMatrixClientPeg.matrixClient.bootstrapCrossSigning({
+            authUploadDeviceSigningKeys: async func => { await func({}); },
+        });
+    });
+});
diff --git a/src/components/views/dialogs/InviteDialog.tsx b/src/components/views/dialogs/InviteDialog.tsx
index 1cc34db875..478a0f8d50 100644
--- a/src/components/views/dialogs/InviteDialog.tsx
+++ b/src/components/views/dialogs/InviteDialog.tsx
@@ -936,6 +936,7 @@ export default class InviteDialog extends React.PureComponent<IInviteDialogProps
                 disabled={this.state.busy || (this.props.kind == KIND_CALL_TRANSFER && this.state.targets.length > 0)}
                 autoComplete="off"
                 placeholder={hasPlaceholder ? _t("Search") : null}
+                data-test-id="invite-dialog-input"
             />
         );
         return (