diff --git a/app/templates/views/check/column-errors.html b/app/templates/views/check/column-errors.html
index 50e68ea73..3269850da 100644
--- a/app/templates/views/check/column-errors.html
+++ b/app/templates/views/check/column-errors.html
@@ -56,32 +56,38 @@
       {% elif not recipients.has_recipient_columns %}
 
         <h1 class='banner-title' data-module="track-error" data-error-type="Missing recipient columns" data-error-label="{{ upload_id }}">
-          Your file needs {{ (
-            recipients.missing_column_headers
-            if template.template_type == 'letter' else required_recipient_columns
-          ) | formatted_list(
-            prefix='a column called',
-            prefix_plural='columns called'
-          ) }}
+          There’s a problem with your column names
         </h1>
-        <p>
-          Right now it has {{ recipients.column_headers | formatted_list(
-            prefix='one column, called ',
-            prefix_plural='columns called '
-          ) }}.
-        </p>
+          <p>
+            Your file needs {{ (
+              recipients.missing_column_headers
+              if template.template_type == 'letter' else required_recipient_columns
+            ) | formatted_list(
+              prefix='a column called',
+              prefix_plural='columns called'
+            ) }}.
+          </p>
+          <p>
+            Right now it has {{ recipients.column_headers | formatted_list(
+              prefix='one column, called ',
+              prefix_plural='columns called '
+            ) }}.
+          </p>
 
       {% elif recipients.duplicate_recipient_column_headers %}
 
         <h1 class='banner-title' data-module="track-error" data-error-type="Duplicate recipient columns" data-error-label="{{ upload_id }}">
-          Your file has more than one column called {{ (
-            recipients.duplicate_recipient_column_headers
-          ) | formatted_list(
-            conjunction='or',
-            prefix='',
-            prefix_plural=''
-          ) }}
+          There’s a problem with your column names
         </h1>
+           <p>
+            We found more than one column called {{ (
+            recipients.duplicate_recipient_column_headers
+            ) | formatted_list(
+              conjunction='or',
+              prefix='',
+              prefix_plural=''
+            ) }}.
+          </p>
         <p>
           Delete or rename one of these columns and try again.
         </p>
@@ -89,16 +95,15 @@
       {% elif recipients.missing_column_headers %}
 
         <h1 class='banner-title' data-module="track-error" data-error-type="Missing placeholder columns" data-error-label="{{ upload_id }}">
-          The columns in your file need to match the double brackets in
-          your template
+          Your column names need to match the double brackets in your template
         </h1>
-        <p>
-          Your file is missing {{ recipients.missing_column_headers | formatted_list(
-            conjunction='and',
-            prefix='a column called ',
-            prefix_plural='columns called '
-          ) }}.
-        </p>
+          <p>
+            Your file is missing {{ recipients.missing_column_headers | formatted_list(
+              conjunction='and',
+              prefix='a column called ',
+              prefix_plural='columns called '
+            ) }}.
+          </p>
 
       {% elif sent_previously %}
 
@@ -141,7 +146,7 @@
         {{ file_upload(
           form.file,
           action=url_for('.send_messages', service_id=current_service.id, template_id=template.id),
-          button_text='Re-upload your file'
+          button_text='Upload your file again'
         ) }}
       {% endif %}
     </div>
diff --git a/tests/app/main/views/test_send.py b/tests/app/main/views/test_send.py
index 9fccd0cb2..c63c9fe29 100644
--- a/tests/app/main/views/test_send.py
+++ b/tests/app/main/views/test_send.py
@@ -427,7 +427,8 @@ def test_upload_csv_file_with_errors_shows_check_page_with_errors(
             +447700900986
         """,
         (
-            'Your file needs a column called ‘phone number’ '
+            'There’s a problem with your column names '
+            'Your file needs a column called ‘phone number’. '
             'Right now it has columns called ‘telephone’ and ‘name’. '
             'Skip to file contents'
         )
@@ -438,7 +439,7 @@ def test_upload_csv_file_with_errors_shows_check_page_with_errors(
             +447700900986
         """,
         (
-            'The columns in your file need to match the double brackets in your template '
+            'Your column names need to match the double brackets in your template '
             'Your file is missing a column called ‘name’. '
             'Skip to file contents'
         )
@@ -449,7 +450,8 @@ def test_upload_csv_file_with_errors_shows_check_page_with_errors(
             +447700900111,+447700900222,+447700900333,
         """,
         (
-            'Your file has more than one column called ‘phone number’ or ‘PHONE_NUMBER’ '
+            'There’s a problem with your column names '
+            'We found more than one column called ‘phone number’ or ‘PHONE_NUMBER’. '
             'Delete or rename one of these columns and try again. '
             'Skip to file contents'
         )
@@ -2863,7 +2865,8 @@ def test_check_messages_column_error_doesnt_show_optional_columns(
     )
 
     assert normalize_spaces(page.select_one('.banner-dangerous').text) == (
-        'Your file needs a column called ‘postcode’ '
+        'There’s a problem with your column names '
+        'Your file needs a column called ‘postcode’. '
         'Right now it has columns called ‘address_line_1’, ‘address_line_2’ and ‘foo’. '
         'Skip to file contents'
     )