diff --git a/app/main/views/send.py b/app/main/views/send.py
index b806af7c5..475e56798 100644
--- a/app/main/views/send.py
+++ b/app/main/views/send.py
@@ -457,14 +457,15 @@ def check_messages(service_id, template_type, upload_id):
         data['recipients'].too_many_rows or
         not data['count_of_recipients'] or
         not data['recipients'].has_recipient_columns or
-        data['recipients'].missing_column_headers
+        data['recipients'].missing_column_headers or
+        data['trying_to_send_letters_in_trial_mode']
     ):
         return render_template('views/check/column-errors.html', **data)
 
     if data['row_errors']:
         return render_template('views/check/row-errors.html', **data)
 
-    if data['errors'] or data['trying_to_send_letters_in_trial_mode']:
+    if data['errors']:
         return render_template('views/check/column-errors.html', **data)
 
     return render_template('views/check/ok.html', **data)
diff --git a/app/templates/views/check/column-errors.html b/app/templates/views/check/column-errors.html
index 9dbd9a548..491eade0f 100644
--- a/app/templates/views/check/column-errors.html
+++ b/app/templates/views/check/column-errors.html
@@ -83,10 +83,6 @@
           {% include "partials/check/not-allowed-to-send-to.html" %}
         {% endwith %}
 
-      {% elif recipients.more_rows_than_can_send %}
-
-        {% include "partials/check/too-many-messages.html" %}
-
       {% elif trying_to_send_letters_in_trial_mode %}
 
         <h1 class='banner-title' data-module="track-error" data-error-type="Trying to send letters in trial mode" data-error-label="{{ upload_id }}">
@@ -98,6 +94,10 @@
           can only preview how your letters will look
         </p>
 
+      {% elif recipients.more_rows_than_can_send %}
+
+        {% include "partials/check/too-many-messages.html" %}
+
       {% endif %}
 
       {{ skip_to_file_contents() }}
diff --git a/tests/app/main/views/test_send.py b/tests/app/main/views/test_send.py
index ad6ef2254..906bfa66f 100644
--- a/tests/app/main/views/test_send.py
+++ b/tests/app/main/views/test_send.py
@@ -1583,6 +1583,10 @@ def test_check_messages_shows_trial_mode_error(
     (mock_get_service, True),
     (mock_get_live_service, False),
 ])
+@pytest.mark.parametrize('number_of_rows, expected_error_message', [
+    (1, 'You can’t send this letter'),
+    (111, 'You can’t send these letters'),
+])
 def test_check_messages_shows_trial_mode_error_for_letters(
     client_request,
     api_user_active,
@@ -1593,14 +1597,16 @@ def test_check_messages_shows_trial_mode_error_for_letters(
     mocker,
     service_mock,
     error_should_be_shown,
+    number_of_rows,
+    expected_error_message,
 ):
 
     service_mock(mocker, api_user_active)
 
-    mocker.patch('app.main.views.send.s3download', return_value='''
-        address_line_1,address_line_2,postcode,
-        First Last,    123 Street,    SW1 1AA
-    ''')
+    mocker.patch('app.main.views.send.s3download', return_value='\n'.join(
+        ['address_line_1,address_line_2,postcode,'] +
+        ['First Last,    123 Street,    SW1 1AA'] * number_of_rows
+    ))
 
     with client_request.session_transaction() as session:
         session['upload_data'] = {'template_id': ''}
@@ -1617,10 +1623,10 @@ def test_check_messages_shows_trial_mode_error_for_letters(
 
     if error_should_be_shown:
         assert normalize_spaces(error[0].text) == (
-            'You can’t send this letter '
+            '{} '
             'In trial mode you can only preview how your letters will look '
             'Skip to file contents'
-        )
+        ).format(expected_error_message)
     else:
         assert not error
 
@@ -1668,7 +1674,7 @@ def test_non_ascii_characters_in_letter_recipients_file_shows_error(
     api_user_active,
     mock_login,
     mock_get_users_by_service,
-    mock_get_service,
+    mock_get_live_service,
     mock_has_permissions,
     mock_get_service_letter_template,
     mock_get_detailed_service_for_today,