diff --git a/testsuite/mailhog.py b/testsuite/mailhog.py
index e4198cad5..646975caa 100644
--- a/testsuite/mailhog.py
+++ b/testsuite/mailhog.py
@@ -44,8 +44,9 @@ def url(self) -> str:
         """Url of the mailhog app"""
         return self._url
 
+    @backoff.on_exception(backoff.expo, requests.exceptions.RequestException, max_tries=3)
     def request(self, method: str = "GET", params: dict = None, endpoint: str = None):
-        """Requests the mailhog API"""
+        """Requests the mailhog API with automatic retry on connection errors"""
         params = params or {}
 
         full_url = f"{self._url}/{endpoint}"
diff --git a/testsuite/tests/system/messages/conftest.py b/testsuite/tests/system/messages/conftest.py
new file mode 100644
index 000000000..4c420740a
--- /dev/null
+++ b/testsuite/tests/system/messages/conftest.py
@@ -0,0 +1,31 @@
+"""
+Conftest for messages tests.
+
+These tests require email notifications to be enabled.
+"""
+
+import pytest
+
+NOTIFICATIONS = [
+    "account_created",
+    "application_created",
+    "service_contract_created",
+    "account_deleted",
+    "service_deleted",
+]
+
+
+@pytest.fixture(scope="session", autouse=True)
+def enable_notifications(threescale):
+    """
+    Enable notification preferences for the current provider's admin user.
+
+    After porta PR #4039, notifications use a per-user NotificationPreferences model
+    instead of account-level settings. In fresh deployments, notifications default to disabled.
+    """
+    params = {f"notification_preferences[{n}]": "true" for n in NOTIFICATIONS}
+    threescale.rest.patch(path="/admin/api/personal/notification_preferences", data=params)
+    # Enable service_plans_ui_visible which defaults to false, gating service_contract_created
+    threescale.rest.put(path="/admin/api/settings", data={"service_plans_ui_visible": "true"})
+
+    yield
diff --git a/testsuite/tests/system/messages/mail_templates.yml b/testsuite/tests/system/messages/mail_templates.yml
index 360ba31a4..4928ad09b 100644
--- a/testsuite/tests/system/messages/mail_templates.yml
+++ b/testsuite/tests/system/messages/mail_templates.yml
@@ -4,7 +4,7 @@ subject_templates:
       Headers: '{"unique_args":{"event_name":"Accounts::AccountCreatedEvent","event_id":".*","user_id":[0-9]+,"account_id":[0-9]+},"category":\["notification","accounts/account_created_event"\]}'
       Body: '----==_mimepart_.+Content-Type: text/plain; charset=UTF-8Content-Transfer-Encoding:
       7bitDear <username>,<test_account> from <test_group> has signed-up for: .+New
-      user details:  Username: <test_account>  Email: <test_account>@<account_email_domain>New
+      user details:  Username: <test_account>  Email: <test_account>@<account_email_domain>.*New
       account details:  Organization/Group Name: <test_group>  To view new signup
       in your 3scale Admin Portal, follow this link: https://3scale-admin.<threescale_superdomain>/buyers/accounts/[0-9]+You
       are receiving this because you subscribed to this notification.View notification
@@ -13,7 +13,7 @@ subject_templates:
       html><html lang=3D"en"><head><meta charset=3D"utf-8" /></head><body style=3D"font-family:
       &#39;Lucida Grande&#39;, verdana, sans-serif;"><p>Dear <username>,</p><p><test_account>
       from <test_group> has signed-up for: .+</p><p><b>New user details:</b></p><ul><li><b>Username:</b>
-      <test_account></li><li><b>Email:</b> <test_account>@<account_email_domain></li></ul><p><b>New
+      <test_account></li><li><b>Email:</b> <test_account>@<account_email_domain></li>.*</ul><p><b>New
       account details:</b></p><ul><li><b>Organization/Group Name:</b> <test_group></li></ul><p><a
       href=3D"https://3scale-admin.<threescale_superdomain>/buyers/accounts/[0-9]+">View
       new signup in your 3scale Admin Portal</a></p><p>=E2=80=94<br />You are receiving
diff --git a/testsuite/tests/system/messages/test_email_accounts.py b/testsuite/tests/system/messages/test_email_accounts.py
index ae0f3de5b..9caf68f3a 100644
--- a/testsuite/tests/system/messages/test_email_accounts.py
+++ b/testsuite/tests/system/messages/test_email_accounts.py
@@ -97,7 +97,7 @@ def test_emails_content_after_account_creation(mailhog_client, mail_template):
         for m in mailhog_client.all_messages()
         if message_match(tpl, "Headers", headers(m).get("X-SMTPAPI", "DO NOT MATCH"))
     ]
-    assert messages, f"Didn't find assumed X-SMTPAPI: {tpl['Headers']}"
+    assert messages, "Didn't find any messages with expected X-SMTPAPI headers"
 
     messages = [
         m