diff --git a/cypress/e2e/crypto/crypto.spec.ts b/cypress/e2e/crypto/crypto.spec.ts
index 650f8d585c3e..f0d9b7a39f46 100644
--- a/cypress/e2e/crypto/crypto.spec.ts
+++ b/cypress/e2e/crypto/crypto.spec.ts
@@ -14,7 +14,7 @@ See the License for the specific language governing permissions and
 limitations under the License.
 */
 
-import { MatrixClient, Room } from "matrix-js-sdk/src/matrix";
+import { MatrixClient, Room, RoomMemberEvent } 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";
@@ -174,4 +174,25 @@ describe("Cryptography", function() {
         testMessages.call(this);
         verify.call(this);
     });
+
+    it("should allow verification when there is no existing DM", function (this: CryptoTestContext) {
+        cy.bootstrapCrossSigning();
+
+        // configure bob to auto-accept the invite
+        this.bob.on(RoomMemberEvent.Membership, (event, member) => {
+            if (member.membership === "invite" && member.userId === this.bob.getUserId()) {
+                this.bob.joinRoom(member.roomId);
+            }
+        });
+
+        /* we need to have a room with the other user present, so we can open the verification panel */
+        let roomId: string;
+        cy.createRoom({ name: "TestRoom", invite: [this.bob.getUserId()]}).then(_room1Id => {
+            roomId = _room1Id;
+            cy.log(`Created test room ${roomId}`);
+            cy.visit(`/#/room/${roomId}`);
+        });
+
+        verify.call(this);
+    });
 });
diff --git a/cypress/support/bot.ts b/cypress/support/bot.ts
index 26f0aa497e48..6161b11cdfb3 100644
--- a/cypress/support/bot.ts
+++ b/cypress/support/bot.ts
@@ -78,6 +78,7 @@ Cypress.Commands.add("getBot", (synapse: SynapseInstance, opts: CreateBotOpts):
     const username = Cypress._.uniqueId("userId_");
     const password = Cypress._.uniqueId("password_");
     return cy.registerUser(synapse, username, password, opts.displayName).then(credentials => {
+        cy.log(`Registered bot user ${username} with displayname ${opts.displayName}`);
         return cy.window({ log: false }).then(win => {
             const cli = new win.matrixcs.MatrixClient({
                 baseUrl: synapse.baseUrl,
diff --git a/cypress/support/login.ts b/cypress/support/login.ts
index e44be7812319..12990fcf065c 100644
--- a/cypress/support/login.ts
+++ b/cypress/support/login.ts
@@ -103,6 +103,7 @@ Cypress.Commands.add("initTestUser", (synapse: SynapseInstance, displayName: str
     return cy.registerUser(synapse, username, password, displayName).then(() => {
         return cy.loginUser(synapse, username, password);
     }).then(response => {
+        cy.log(`Registered test user ${username} with displayname ${displayName}`);
         cy.window({ log: false }).then(win => {
             // Seed the localStorage with the required credentials
             win.localStorage.setItem("mx_hs_url", synapse.baseUrl);