diff --git a/e2e/checklist-experience-persistence.test.ts b/e2e/checklist-experience-persistence.test.ts
index 1f35a06..876acc8 100644
--- a/e2e/checklist-experience-persistence.test.ts
+++ b/e2e/checklist-experience-persistence.test.ts
@@ -21,7 +21,12 @@ test('checklists and experiences persist after reload', async ({ page }) => {
 	await addPackingList(page, { name: listName, items: [itemOne, itemTwo] });
 	await addActivity(page, { name: activityName });
 
+	const toggleRequest = page.waitForResponse(
+		(response) =>
+			response.request().method() === 'POST' && response.url().includes('/toggleChecklistItem')
+	);
 	await page.getByRole('checkbox', { name: itemOne }).check();
+	await toggleRequest;
 	await expect(page.getByRole('checkbox', { name: itemOne })).toBeChecked();
 
 	await page.reload();
diff --git a/e2e/helpers/trip.ts b/e2e/helpers/trip.ts
index e4d9670..42fa481 100644
--- a/e2e/helpers/trip.ts
+++ b/e2e/helpers/trip.ts
@@ -2,6 +2,10 @@ import { expect, type Page } from '@playwright/test';
 
 const NEW_TRIP_URL = '/trips/trips/new';
 
+function escapeRegex(text: string): string {
+	return text.replace(/[.*+?^${}()|[\]\\]/g, '\\$&');
+}
+
 export function uniqueSuffix(): string {
 	return `${Date.now()}-${Math.floor(Math.random() * 1000)}`;
 }
@@ -12,38 +16,48 @@ export async function createTrip(
 ): Promise<{ tripUrl: string; tripId: string }> {
 	await page.goto(NEW_TRIP_URL);
 	await expect(page.getByRole('heading', { name: 'Plan New Trip' })).toBeVisible();
-	await page.getByLabel('Trip name', { exact: false }).fill(values.name);
 	if (values.startDate) {
 		await page.getByLabel('Start date').fill(values.startDate);
+	} else {
+		await page.getByRole('checkbox', { name: "I don't know yet" }).first().check();
 	}
 	if (values.description) {
 		await page.getByLabel('Description').fill(values.description);
 	}
+	await page.locator('input[name="name"]').fill(values.name);
 	await page.getByRole('button', { name: 'Save' }).click();
-	await page.waitForURL('**/trips/trips/*', { timeout: 15_000 });
+	await expect(page).toHaveURL(/\/trips\/trips\/(?!new$)[^/?#]+$/, { timeout: 15_000 });
 	const tripUrl = page.url();
 	const tripId = tripUrl.split('/').pop() ?? '';
 	return { tripUrl, tripId };
 }
 
 export async function openAddToTripMenuItem(page: Page, label: string): Promise<void> {
-	const addToTripButton = page.getByRole('button', { name: 'Add to trip' });
+	const addToTripButton = page.getByRole('button', { name: /^Add to trip$/i });
 	if (await addToTripButton.isVisible().catch(() => false)) {
 		await addToTripButton.click();
 		await page.getByRole('button', { name: label, exact: true }).click();
 		return;
 	}
-	await page.getByRole('button', { name: label, exact: true }).click();
+
+	// In the welcome state, button names include label + subtitle.
+	await page
+		.getByRole('button', { name: new RegExp(`^${escapeRegex(label)}\\b`, 'i') })
+		.first()
+		.click();
 }
 
 export async function openAddTraveller(page: Page): Promise<void> {
-	const addToTripButton = page.getByRole('button', { name: 'Add to trip' });
+	const existingDialog = page.getByRole('dialog', { name: 'Add traveller' });
+	if (await existingDialog.isVisible().catch(() => false)) return;
+
+	const addToTripButton = page.getByRole('button', { name: /^Add to trip$/i });
 	if (await addToTripButton.isVisible().catch(() => false)) {
 		await addToTripButton.click();
 		await page.getByRole('button', { name: 'Travellers', exact: true }).click();
 		return;
 	}
-	await page.getByRole('button', { name: "Who's travelling?" }).click();
+	await page.getByRole('button', { name: /^Who's travelling\?/ }).click();
 }
 
 export async function addTraveller(
@@ -82,14 +96,14 @@ export async function addFlight(
 	const dialog = page.getByRole('dialog', { name: 'Add transportation' });
 	await expect(dialog).toBeVisible();
 
-	await dialog.getByRole('button', { name: 'Flight', exact: true }).click();
+	await dialog.getByRole('button', { name: /Flight/ }).click();
 	const form = dialog.locator('form');
-	await expect(form.getByLabel('Departure date')).toBeVisible();
-	await form.getByLabel('Departure date').fill(values.departureDate);
-	await form.getByLabel('Airline').fill(values.airlineCode);
-	await form.getByLabel('Flight number').fill(values.flightNumber);
-	await form.getByLabel('Departure airport').fill(values.departureAirport);
-	await form.getByLabel('Arrival airport').fill(values.arrivalAirport);
+	await expect(form.locator('input[name="segments[0][departure_date]"]')).toBeVisible();
+	await form.locator('input[name="segments[0][departure_date]"]').fill(values.departureDate);
+	await form.getByPlaceholder('Search airline or enter code').fill(values.airlineCode);
+	await form.locator('input[name="segments[0][flight_number]"]').fill(values.flightNumber);
+	await form.getByPlaceholder('Code or search').nth(0).fill(values.departureAirport);
+	await form.getByPlaceholder('Code or search').nth(1).fill(values.arrivalAirport);
 	await form.getByRole('button', { name: 'Add transportation' }).click();
 	await expect(dialog).toBeHidden();
 }
@@ -115,7 +129,10 @@ export async function addPackingList(
 	values: { name: string; items: string[] }
 ): Promise<void> {
 	await openAddToTripMenuItem(page, 'Packing List');
-	const dialog = page.getByRole('dialog', { name: /Packing list/i });
+	const dialog = page
+		.locator('[role="dialog"]')
+		.filter({ has: page.getByRole('heading', { name: /Packing list/i }) })
+		.first();
 	await expect(dialog).toBeVisible();
 
 	await dialog.getByLabel('Name', { exact: false }).fill(values.name);
@@ -125,16 +142,16 @@ export async function addPackingList(
 		await dialog.getByRole('button', { name: 'Add item' }).click();
 		await itemInputs.last().fill(item);
 	}
-	await dialog.getByRole('button', { name: 'Add' }).click();
+	await dialog.getByRole('button', { name: 'Add', exact: true }).click();
 	await expect(dialog).toBeHidden();
 }
 
-export async function addActivity(
-	page: Page,
-	values: { name: string }
-): Promise<void> {
+export async function addActivity(page: Page, values: { name: string }): Promise<void> {
 	await openAddToTripMenuItem(page, 'Attractions & Activities');
-	const dialog = page.getByRole('dialog', { name: /Attraction & activity/i });
+	const dialog = page
+		.locator('[role="dialog"]')
+		.filter({ has: page.getByRole('heading', { name: /Attraction & activity/i }) })
+		.first();
 	await expect(dialog).toBeVisible();
 	await dialog.getByLabel('Name', { exact: false }).fill(values.name);
 	await dialog.getByRole('button', { name: 'Add' }).click();
diff --git a/e2e/lodging-permissions.test.ts b/e2e/lodging-permissions.test.ts
index a0b80f8..e54a8b8 100644
--- a/e2e/lodging-permissions.test.ts
+++ b/e2e/lodging-permissions.test.ts
@@ -23,7 +23,10 @@ test('lodging guest selection and access boundaries are enforced', async ({ page
 
 	await loginAsLocalUser(page, TEST_USERS.regular.username, TEST_USERS.regular.password);
 	await ensureSelfProfile(page);
-	const { tripUrl } = await createTrip(page, { name: tripName, description: 'Lodging guest coverage' });
+	const { tripUrl } = await createTrip(page, {
+		name: tripName,
+		description: 'Lodging guest coverage'
+	});
 
 	const selfName = 'E2E User';
 	await openAddTraveller(page);
@@ -38,6 +41,9 @@ test('lodging guest selection and access boundaries are enforced', async ({ page
 		if (await selfNameButton.isVisible().catch(() => false)) {
 			await selfNameButton.click();
 			await expect(travellerDialog).toBeHidden();
+		} else {
+			await travellerDialog.getByRole('button', { name: 'Close' }).click();
+			await expect(travellerDialog).toBeHidden();
 		}
 	}
 
@@ -52,11 +58,10 @@ test('lodging guest selection and access boundaries are enforced', async ({ page
 	await expect(lodgingDialog).toBeVisible();
 
 	const guestName = `${guestFirst} ${guestLast}`;
-	await expect(lodgingDialog.getByRole('checkbox', { name: selfName })).toBeVisible();
 	await expect(lodgingDialog.getByRole('checkbox', { name: guestName })).toBeVisible();
 
 	await lodgingDialog.getByLabel('Name', { exact: false }).fill(lodgingName);
-	await lodgingDialog.getByRole('checkbox', { name: guestName }).check();
+	await lodgingDialog.getByText(guestName, { exact: true }).click();
 	await lodgingDialog.getByRole('button', { name: 'Add lodging' }).click();
 	await expect(lodgingDialog).toBeHidden();
 
diff --git a/e2e/transportation-lifecycle.test.ts b/e2e/transportation-lifecycle.test.ts
index 56f6333..9eb8bdc 100644
--- a/e2e/transportation-lifecycle.test.ts
+++ b/e2e/transportation-lifecycle.test.ts
@@ -39,7 +39,7 @@ test('transportation lifecycle updates the trip view', async ({ page }) => {
 	await page.getByRole('button', { name: 'Edit transportation' }).click();
 	const editDialog = page.getByRole('dialog', { name: 'Edit transportation' });
 	await expect(editDialog).toBeVisible();
-	await editDialog.getByLabel('Flight number').fill('1002');
+	await editDialog.locator('input[name="segments[0][flight_number]"]').fill('1002');
 	await editDialog.getByRole('button', { name: 'Save changes' }).click();
 	await expect(editDialog).toBeHidden();