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diff --git a/testing/web-platform/tests/payment-request/PaymentRequestUpdateEvent/updateWith-call-immediate-manual.https.html b/testing/web-platform/tests/payment-request/PaymentRequestUpdateEvent/updateWith-call-immediate-manual.https.html
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+++ b/testing/web-platform/tests/payment-request/PaymentRequestUpdateEvent/updateWith-call-immediate-manual.https.html
@@ -0,0 +1,206 @@
+<!doctype html>
+<meta charset="utf8">
+<link rel="help" href="https://www.w3.org/TR/payment-request/#updatewith()-method">
+<link rel="help" href="https://github.com/w3c/payment-request/pull/591">
+<title>
+  PaymentRequestUpdateEvent.updateWith() needs to be called immediately
+</title>
+<script src="/resources/testharness.js"></script>
+<script src="/resources/testharnessreport.js"></script>
+<script>
+setup({ explicit_done: true, explicit_timeout: true });
+const applePay = Object.freeze({
+  supportedMethods: "https://apple.com/apple-pay",
+  data: {
+    version: 3,
+    merchantIdentifier: "merchant.com.example",
+    countryCode: "US",
+    merchantCapabilities: ["supports3DS"],
+    supportedNetworks: ["visa"],
+  }
+});
+const validMethod = Object.freeze({ supportedMethods: "basic-card" });
+const validMethods = Object.freeze([validMethod, applePay]);
+const validAmount = Object.freeze({ currency: "USD", value: "5.00" });
+const validTotal = Object.freeze({
+  label: "label",
+  amount: validAmount,
+});
+const validShippingOptionA = Object.freeze({
+  id: "a-shipping-option",
+  label: "A shipping option",
+  amount: validAmount,
+  selected: true,
+});
+const validShippingOptionB = Object.freeze({
+  id: "b-shipping-option",
+  label: "B shipping option",
+  amount: validAmount,
+});
+const validDetails = Object.freeze({
+  total: validTotal,
+  shippingOptions: [validShippingOptionA, validShippingOptionB],
+});
+const validOptions = Object.freeze({
+  requestShipping: true,
+});
+
+function testImmediateUpdate({ textContent: testName }) {
+  promise_test(async t => {
+    const request = new PaymentRequest(
+      validMethods,
+      validDetails,
+      validOptions
+    );
+    const eventPromise = new Promise((resolve, reject) => {
+      request.addEventListener(
+        "shippingaddresschange",
+        ev => {
+          // Forces updateWith() to be run in the next event loop tick so that
+          // [[waitForUpdate]] is already true when it runs.
+          t.step_timeout(() => {
+            try {
+              ev.updateWith(validDetails);
+              resolve(); // This is bad.
+            } catch (err) {
+              reject(err); // this is good.
+            }
+          });
+        },
+        { once: true }
+      );
+    });
+    const acceptPromise = request.show();
+    await promise_rejects_dom(
+      t,
+      "InvalidStateError",
+      eventPromise,
+      "The event loop already spun, so [[waitForUpdate]] is now true"
+    );
+    const response = await acceptPromise;
+    await response.complete();
+  }, testName.trim());
+}
+
+function testSubsequentUpdateWithCalls({ textContent: testName }) {
+  promise_test(async t => {
+    const request = new PaymentRequest(
+      validMethods,
+      validDetails,
+      validOptions
+    );
+    const eventPromise = new Promise((resolve, reject) => {
+      request.addEventListener("shippingaddresschange", async ev => {
+        const p = Promise.resolve(validDetails);
+        ev.updateWith(p);
+        await p;
+        try {
+          ev.updateWith(validDetails);
+          resolve(); // this is bad, we should never get to here.
+        } catch (err) {
+          reject(err); // this is good!
+        }
+      });
+    });
+    const responsePromise = request.show();
+    await promise_rejects_dom(
+      t,
+      "InvalidStateError",
+      eventPromise,
+      "Expected eventPromise to have rejected, because updateWith() was a called twice"
+    );
+    const response = await responsePromise;
+    await response.complete();
+  }, testName.trim());
+}
+
+function testRecycleEvents({ textContent: testName }) {
+  promise_test(async t => {
+    const request = new PaymentRequest(
+      validMethods,
+      validDetails,
+      validOptions
+    );
+
+    // Register both listeners.
+    const addressChangedPromise = new Promise(resolve => {
+      request.addEventListener("shippingaddresschange", resolve, {
+        once: true,
+      });
+    });
+
+    const optionChangedPromise = new Promise(resolve => {
+      request.addEventListener("shippingoptionchange", resolve, {
+        once: true,
+      });
+    });
+
+    const responsePromise = request.show();
+
+    // Let's wait for the address to change.
+    const addressChangeEvent = await addressChangedPromise;
+
+    // Sets [[waitingForUpdate]] to true.
+    addressChangeEvent.updateWith(validDetails);
+
+    // Let's wait for the shippingOption.
+    const optionChangeEvent = await optionChangedPromise;
+
+    // Here, we try to be sneaky, and reuse the addressChangeEvent to perform the update.
+    // However, addressChangeEvent [[waitingForUpdate]] is true, so it throws.
+    assert_throws_dom(
+      "InvalidStateError",
+      () => {
+        addressChangeEvent.updateWith(validDetails);
+      },
+      "addressChangeEvent [[waitingForUpdate]] is true, so it must throw"
+    );
+
+    // But optionChangeEvent is still usable tho, so...
+    optionChangeEvent.updateWith(validDetails);
+
+    assert_throws_dom(
+      "InvalidStateError",
+      () => {
+        optionChangeEvent.updateWith(validDetails);
+      },
+      "optionChangeEvent [[waitingForUpdate]] is true, so it must throw"
+    );
+
+    const response = await responsePromise;
+    await response.complete();
+  }, testName.trim());
+}
+</script>
+<h2>updateWith() method</h2>
+<p>
+  Click on each button in sequence from top to bottom without refreshing the page.
+  Each button will bring up the Payment Request UI window.
+</p>
+<p>
+  When the payment sheet is shown, select a different shipping address once. Then pay.
+</p>
+<ol>
+  <li id="test-0">
+    <button onclick="testImmediateUpdate(this);">
+      updateWith() must be called immediately, otherwise must throw an InvalidStateError.
+    </button>
+  </li>
+  <li id="test-1">
+    <button onclick="testSubsequentUpdateWithCalls(this);">
+      Once the event has performed an update, subsequent calls to updateWith() must throw InvalidStateError.
+    </button>
+  </li>
+  <li id="test-2">
+    <button onclick="testRecycleEvents(this);">
+      Recycling events must not be possible.
+    </button> When the payment sheet is shown, select a different shipping address once, then change shipping option once. Then pay.
+  </li>
+  <li>
+    <button onclick="done();">Done!</button>
+  </li>
+</ol>
+<small>
+  If you find a buggy test, please <a href="https://github.com/web-platform-tests/wpt/issues">file a bug</a>
+  and tag one of the <a href="https://github.com/web-platform-tests/wpt/blob/master/payment-request/META.yml">suggested reviewers</a>.
+</small>