diff --git a/src/tests/e2e/conftest.py b/src/tests/e2e/conftest.py
index 6eb4df0f5..c93318ec7 100644
--- a/src/tests/e2e/conftest.py
+++ b/src/tests/e2e/conftest.py
@@ -1205,7 +1205,7 @@ def _register_widget_test_view():
     <link rel="stylesheet" type="text/css" href="{widget_css}" crossorigin>
 </head>
 <body>
-    <pretix-button event="{event_url}"{extra_attrs}>{button_text}</pretix-button>
+    <pretix-button event="{event_url}"{extra_attrs} skip-ssl-check>{button_text}</pretix-button>
     {script_tag}
 </body>
 </html>"""
diff --git a/src/tests/e2e/test_widget_button.py b/src/tests/e2e/test_widget_button.py
new file mode 100644
index 000000000..e3de0bb41
--- /dev/null
+++ b/src/tests/e2e/test_widget_button.py
@@ -0,0 +1,73 @@
+import pytest
+from playwright.sync_api import Page, expect
+
+
+@pytest.mark.django_db
+class TestButtonJourney:
+    """
+    Complete purchase journeys for a regular event.
+    Tests item visibility, variation visibility, adding items and variations to cart, and checkout up until showing the iframe.
+    """
+
+    def test_no_predefined_items_journey(
+        self,
+        page: Page,
+        live_server_url: str,
+        organizer,
+        event,
+        items,
+        widget_page
+    ):
+
+        widget_page.goto_button_test_page(
+            live_server_url, organizer.slug, event.slug)
+
+        button = page.locator('.pretix-button')
+        button.click()
+        iframe = widget_page.wait_for_iframe_checkout()
+
+        expect(iframe.locator('#btn-add-to-cart')).to_be_visible(timeout=15000)
+
+    def test_predefined_items_journey(
+        self,
+        page: Page,
+        live_server_url: str,
+        organizer,
+        event,
+        items,
+        widget_page
+    ):
+        item_str = ','.join(f'item_{item.pk}=1' for item in items)
+
+        widget_page.goto_button_test_page(
+            live_server_url, organizer.slug, event.slug, items=item_str)
+
+        button = page.locator('.pretix-button')
+        button.click()
+        iframe = widget_page.wait_for_iframe_checkout()
+
+        # TODO a bit janky selector
+        expect(iframe.locator('text=/200\\.00/')).to_be_visible(timeout=15000)
+
+    def test_subevent_button_journey(
+        self,
+        page: Page,
+        live_server_url: str,
+        organizer,
+        event_series,
+        widget_page
+    ):
+        event, subevents = event_series
+        subevent = subevents[2]
+
+        widget_page.goto_button_test_page(
+            live_server_url, organizer.slug, event.slug,
+            subevent=str(subevent.pk))
+
+        button = page.locator('.pretix-button')
+        button.click()
+        iframe = widget_page.wait_for_iframe_checkout()
+
+        expect(iframe.locator('#btn-add-to-cart')).to_be_visible(timeout=15000)
+        page.pause()
+        expect(iframe.get_by_role('heading', name='Concert Night 3')).to_be_visible(timeout=15000)
