diff --git a/app/main/forms.py b/app/main/forms.py
index ebec282f8..65877e997 100644
--- a/app/main/forms.py
+++ b/app/main/forms.py
@@ -1111,8 +1111,8 @@ class PDFUploadForm(StripWhitespaceForm):
     file = FileField_wtf(
         'Upload a letter in PDF format',
         validators=[
-            FileAllowed(['pdf'], 'Letters must be saved as a PDF'),
-            DataRequired(message="You need to upload a file to submit")
+            FileAllowed(['pdf'], 'Save your letter as a PDF and try again.'),
+            DataRequired(message="You need to choose a file to upload")
         ]
     )
 
diff --git a/app/main/views/uploads.py b/app/main/views/uploads.py
index 31d3a4f46..7b2dc65ae 100644
--- a/app/main/views/uploads.py
+++ b/app/main/views/uploads.py
@@ -1,11 +1,11 @@
 import base64
+import json
 import uuid
 from io import BytesIO
 
 from flask import (
     abort,
     current_app,
-    flash,
     redirect,
     render_template,
     request,
@@ -26,7 +26,11 @@ from app.s3_client.s3_letter_upload_client import (
     upload_letter_to_s3,
 )
 from app.template_previews import TemplatePreview, sanitise_letter
-from app.utils import get_template, user_has_permissions
+from app.utils import (
+    get_letter_validation_error,
+    get_template,
+    user_has_permissions,
+)
 
 MAX_FILE_UPLOAD_SIZE = 2 * 1024 * 1024  # 2MB
 
@@ -41,6 +45,7 @@ def uploads(service_id):
 @user_has_permissions('send_messages')
 def upload_letter(service_id):
     form = PDFUploadForm()
+    error = {}
 
     if form.validate_on_submit():
         pdf_file_bytes = form.file.data.read()
@@ -48,17 +53,20 @@ def upload_letter(service_id):
 
         virus_free = antivirus_client.scan(BytesIO(pdf_file_bytes))
         if not virus_free:
-            return invalid_upload_error('Your file has failed the virus check')
+            return invalid_upload_error('Your file contains a virus')
 
         if len(pdf_file_bytes) > MAX_FILE_UPLOAD_SIZE:
-            return invalid_upload_error('Your file must be smaller than 2MB')
+            return invalid_upload_error('Your file is too big', 'Files must be smaller than 2MB.')
 
         try:
             # TODO: get page count from the sanitise response once template preview handles malformed files nicely
             page_count = pdf_page_count(BytesIO(pdf_file_bytes))
         except PdfReadError:
             current_app.logger.info('Invalid PDF uploaded for service_id: {}'.format(service_id))
-            return invalid_upload_error('Your file must be a valid PDF')
+            return invalid_upload_error(
+                "There’s a problem with your file",
+                'Notify cannot read this PDF.<br>Save a new copy of your file and try again.'
+            )
 
         upload_id = uuid.uuid4()
         file_location = get_transient_letter_file_location(service_id, upload_id)
@@ -68,13 +76,18 @@ def upload_letter(service_id):
             response.raise_for_status()
         except RequestException as ex:
             if ex.response is not None and ex.response.status_code == 400:
+                validation_failed_message = response.json().get('message')
+                invalid_pages = response.json().get('invalid_pages')
+
                 status = 'invalid'
                 upload_letter_to_s3(
                     pdf_file_bytes,
                     file_location=file_location,
                     status=status,
                     page_count=page_count,
-                    filename=original_filename)
+                    filename=original_filename,
+                    message=validation_failed_message,
+                    invalid_pages=invalid_pages)
             else:
                 raise ex
         else:
@@ -95,12 +108,33 @@ def upload_letter(service_id):
             )
         )
 
-    return render_template('views/uploads/choose-file.html', form=form)
+    if form.file.errors:
+        error = _get_error_from_upload_form(form.file.errors[0])
+
+    return render_template(
+        'views/uploads/choose-file.html',
+        error=error,
+        form=form
+    )
 
 
-def invalid_upload_error(message):
-    flash(message, 'dangerous')
-    return render_template('views/uploads/choose-file.html', form=PDFUploadForm()), 400
+def invalid_upload_error(error_title, error_detail=None):
+    return render_template(
+        'views/uploads/choose-file.html',
+        error={'title': error_title, 'detail': error_detail},
+        form=PDFUploadForm()
+    ), 400
+
+
+def _get_error_from_upload_form(form_errors):
+    error = {}
+    if 'PDF' in form_errors:
+        error['title'] = 'Wrong file type'
+        error['detail'] = form_errors
+    else:  # No file was uploaded error
+        error['title'] = form_errors
+
+    return error
 
 
 @main.route("/services/<service_id>/preview-letter/<file_id>")
@@ -110,7 +144,13 @@ def uploaded_letter_preview(service_id, file_id):
     original_filename = metadata.get('filename')
     page_count = metadata.get('page_count')
     status = metadata.get('status')
+    error_message = metadata.get('message')
+    invalid_pages = metadata.get('invalid_pages')
 
+    if invalid_pages:
+        invalid_pages = json.loads(invalid_pages)
+
+    error = get_letter_validation_error(error_message, invalid_pages, page_count)
     template_dict = service_api_client.get_precompiled_template(service_id)
 
     template = get_template(
@@ -130,6 +170,7 @@ def uploaded_letter_preview(service_id, file_id):
         template=template,
         status=status,
         file_id=file_id,
+        error=error,
     )
 
 
diff --git a/app/templates/components/file-upload.html b/app/templates/components/file-upload.html
index 78598ca8a..b7acf0c56 100644
--- a/app/templates/components/file-upload.html
+++ b/app/templates/components/file-upload.html
@@ -4,10 +4,11 @@
   button_text="Choose file",
   alternate_link=None,
   alternate_link_text=None,
-  hint=None
+  hint=None,
+  show_errors=True
 
 ) %}
-  <form method="post" enctype="multipart/form-data" {% if action %}action="{{ action }}"{% endif %} class="{% if field.errors %}form-group-error{% endif %}" data-module="file-upload">
+  <form method="post" enctype="multipart/form-data" {% if action %}action="{{ action }}"{% endif %} class="{% if field.errors and show_errors %}form-group-error{% endif %}" data-module="file-upload">
     <label class="file-upload-label" for="{{ field.name }}">
       <span class="visually-hidden">{{ field.label.text }}</span>
       {% if hint %}
@@ -15,7 +16,7 @@
           {{ hint }}
         </span>
       {% endif %}
-      {% if field.errors %}
+      {% if field.errors and show_errors %}
         <span class="error-message">
           {{ field.errors[0] }}
         </span>
diff --git a/app/templates/views/uploads/choose-file.html b/app/templates/views/uploads/choose-file.html
index d75e32fe6..478af1e46 100644
--- a/app/templates/views/uploads/choose-file.html
+++ b/app/templates/views/uploads/choose-file.html
@@ -1,4 +1,5 @@
 {% extends "withnav_template.html" %}
+{% from "components/banner.html" import banner_wrapper %}
 {% from "components/file-upload.html" import file_upload %}
 {% from "components/page-header.html" import page_header %}
 
@@ -9,15 +10,26 @@
 {% block maincolumn_content %}
 <div class="grid-row">
   <div class="column-five-sixths">
-    {{ page_header(
+    {% if error %}
+      {% call banner_wrapper(type='dangerous') %}
+        <h1 class="banner-title">{{ error.title }}</h1>
+        {% if error.detail %}
+          <p>{{ error.detail | safe }}</p>
+        {% endif %}
+      {% endcall %}
+    {% else %}
+      {{ page_header(
         'Upload a letter',
         back_link=url_for('main.uploads', service_id=current_service.id)
     ) }}
+    {% endif %}
 
   <p>
     {{ file_upload(
       form.file,
-      action = url_for('main.upload_letter', service_id=current_service.id),
+      action=url_for('main.upload_letter', service_id=current_service.id),
+      button_text='Upload your file again' if error else 'Choose file',
+      show_errors=False
     )}}
   </p>
   <p>You can upload a single letter as a PDF.</p>
diff --git a/app/templates/views/uploads/preview.html b/app/templates/views/uploads/preview.html
index 5642540e0..8ecc96a3e 100644
--- a/app/templates/views/uploads/preview.html
+++ b/app/templates/views/uploads/preview.html
@@ -1,4 +1,5 @@
 {% extends "withnav_template.html" %}
+{% from "components/banner.html" import banner_wrapper %}
 {% from "components/page-header.html" import page_header %}
 
 {% block service_page_title %}
@@ -6,16 +7,19 @@
 {% endblock %}
 
 {% block maincolumn_content %}
-    {{ page_header(
+  {% if status == 'invalid' and error %}
+    {% call banner_wrapper(type='dangerous') %}
+      <h1 class="banner-title">{{ error.title }}</h1>
+      {% if error.detail %}
+        <p>{{ error.detail | safe }}</p>
+      {% endif %}
+    {% endcall %}
+  {% else %}
+      {{ page_header(
         original_filename,
         back_link=url_for('main.upload_letter', service_id=current_service.id)
-    ) }}
-
-    {% if status == 'invalid' %}
-    <p class="notification-status-cancelled" id="validation-error-message">
-      Validation failed
-    </p>
-    {% endif %}
+      ) }}
+  {% endif %}
 
     <div class="letter-sent">
       {{ template|string }}
diff --git a/tests/app/main/views/test_platform_admin.py b/tests/app/main/views/test_platform_admin.py
index 7e58dac2a..813955fcd 100644
--- a/tests/app/main/views/test_platform_admin.py
+++ b/tests/app/main/views/test_platform_admin.py
@@ -789,7 +789,7 @@ def test_letter_validation_preview_doesnt_call_template_preview_when_no_file(moc
     validate_letter.assert_not_called()
 
     page = BeautifulSoup(response.data.decode('utf-8'), 'html.parser')
-    assert page.find('span', class_='error-message').text.strip() == "You need to upload a file to submit"
+    assert page.find('span', class_='error-message').text.strip() == "You need to choose a file to upload"
 
 
 def test_letter_validation_preview_doesnt_call_template_preview_when_file_not_pdf(mocker, platform_admin_client):
@@ -805,7 +805,7 @@ def test_letter_validation_preview_doesnt_call_template_preview_when_file_not_pd
     antivirus_scan.assert_not_called()
     validate_letter.assert_not_called()
     page = BeautifulSoup(response.data.decode('utf-8'), 'html.parser')
-    assert page.find('span', class_='error-message').text.strip() == "Letters must be saved as a PDF"
+    assert page.find('span', class_='error-message').text.strip() == "Save your letter as a PDF and try again."
 
 
 def test_letter_validation_preview_doesnt_call_template_preview_when_file_doesnt_pass_virus_scan(
diff --git a/tests/app/main/views/test_uploads.py b/tests/app/main/views/test_uploads.py
index e58031e0f..aa5b377fe 100644
--- a/tests/app/main/views/test_uploads.py
+++ b/tests/app/main/views/test_uploads.py
@@ -23,6 +23,7 @@ def test_get_upload_letter(client_request):
     assert page.find('h1').text == 'Upload a letter'
     assert page.find('input', class_='file-upload-field')
     assert page.select('button[type=submit]')
+    assert normalize_spaces(page.find('label', class_='file-upload-button').text) == 'Choose file'
 
 
 def test_post_upload_letter_redirects_for_valid_file(mocker, client_request):
@@ -88,6 +89,7 @@ def test_post_upload_letter_shows_letter_preview_for_valid_file(mocker, client_r
             _follow_redirects=True,
         )
 
+    assert page.find('h1').text == 'tests/test_pdf_files/one_page_pdf.pdf'
     assert len(page.select('.letter-postage')) == 1
     assert normalize_spaces(page.select_one('.letter-postage').text) == ('Postage: second class')
     assert page.select_one('.letter-postage')['class'] == ['letter-postage', 'letter-postage-second']
@@ -111,7 +113,9 @@ def test_post_upload_letter_shows_error_when_file_is_not_a_pdf(client_request):
             _data={'file': file},
             _expected_status=200
         )
-    assert page.find('span', class_='error-message').text.strip() == "Letters must be saved as a PDF"
+    assert page.find('h1').text == 'Wrong file type'
+    assert page.find('div', class_='banner-dangerous').find('p').text == 'Save your letter as a PDF and try again.'
+    assert normalize_spaces(page.find('label', class_='file-upload-button').text) == 'Upload your file again'
 
 
 def test_post_upload_letter_shows_error_when_no_file_uploaded(client_request):
@@ -121,7 +125,8 @@ def test_post_upload_letter_shows_error_when_no_file_uploaded(client_request):
         _data={'file': ''},
         _expected_status=200
     )
-    assert page.find('span', class_='error-message').text.strip() == "You need to upload a file to submit"
+    assert page.find('div', class_='banner-dangerous').find('h1').text == 'You need to choose a file to upload'
+    assert normalize_spaces(page.find('label', class_='file-upload-button').text) == 'Upload your file again'
 
 
 def test_post_upload_letter_shows_error_when_file_contains_virus(mocker, client_request):
@@ -134,8 +139,8 @@ def test_post_upload_letter_shows_error_when_file_contains_virus(mocker, client_
             _data={'file': file},
             _expected_status=400
         )
-    assert page.find('h1').text == 'Upload a letter'
-    assert normalize_spaces(page.select('.banner-dangerous')[0].text) == 'Your file has failed the virus check'
+    assert page.find('div', class_='banner-dangerous').find('h1').text == 'Your file contains a virus'
+    assert normalize_spaces(page.find('label', class_='file-upload-button').text) == 'Upload your file again'
 
 
 def test_post_choose_upload_file_when_file_is_too_big(mocker, client_request):
@@ -148,8 +153,9 @@ def test_post_choose_upload_file_when_file_is_too_big(mocker, client_request):
             _data={'file': file},
             _expected_status=400
         )
-    assert page.find('h1').text == 'Upload a letter'
-    assert normalize_spaces(page.select('.banner-dangerous')[0].text) == 'Your file must be smaller than 2MB'
+    assert page.find('div', class_='banner-dangerous').find('h1').text == 'Your file is too big'
+    assert page.find('div', class_='banner-dangerous').find('p').text == 'Files must be smaller than 2MB.'
+    assert normalize_spaces(page.find('label', class_='file-upload-button').text) == 'Upload your file again'
 
 
 def test_post_choose_upload_file_when_file_is_malformed(mocker, client_request):
@@ -162,8 +168,11 @@ def test_post_choose_upload_file_when_file_is_malformed(mocker, client_request):
             _data={'file': file},
             _expected_status=400
         )
-    assert page.find('h1').text == 'Upload a letter'
-    assert normalize_spaces(page.select('.banner-dangerous')[0].text) == 'Your file must be a valid PDF'
+    assert page.find('div', class_='banner-dangerous').find('h1').text == "There’s a problem with your file"
+    assert page.find(
+        'div', class_='banner-dangerous'
+    ).find('p').text == 'Notify cannot read this PDF.Save a new copy of your file and try again.'
+    assert normalize_spaces(page.find('label', class_='file-upload-button').text) == 'Upload your file again'
 
 
 def test_post_upload_letter_with_invalid_file(mocker, client_request):
@@ -173,10 +182,15 @@ def test_post_upload_letter_with_invalid_file(mocker, client_request):
 
     mock_sanitise_response = Mock()
     mock_sanitise_response.raise_for_status.side_effect = RequestException(response=Mock(status_code=400))
+    mock_sanitise_response.json = lambda: {
+        "message": "content-outside-printable-area",
+        "invalid_pages": [1]
+    }
     mocker.patch('app.main.views.uploads.sanitise_letter', return_value=mock_sanitise_response)
     mocker.patch('app.main.views.uploads.service_api_client.get_precompiled_template')
     mocker.patch('app.main.views.uploads.get_letter_metadata', return_value={
-        'filename': 'tests/test_pdf_files/one_page_pdf.pdf', 'page_count': '1', 'status': 'invalid'})
+        'filename': 'tests/test_pdf_files/one_page_pdf.pdf', 'page_count': '1', 'status': 'invalid',
+        'message': 'content-outside-printable-area', 'invalid_pages': '[1]'})
 
     with open('tests/test_pdf_files/one_page_pdf.pdf', 'rb') as file:
         file_contents = file.read()
@@ -194,13 +208,16 @@ def test_post_upload_letter_with_invalid_file(mocker, client_request):
             file_location='service-{}/fake-uuid.pdf'.format(SERVICE_ONE_ID),
             status='invalid',
             page_count=1,
-            filename='tests/test_pdf_files/one_page_pdf.pdf'
+            filename='tests/test_pdf_files/one_page_pdf.pdf',
+            invalid_pages=[1],
+            message='content-outside-printable-area'
         )
 
-    assert page.find('h1').text == 'tests/test_pdf_files/one_page_pdf.pdf'
-    assert normalize_spaces(
-        page.find(id='validation-error-message').text
-    ) == 'Validation failed'
+    assert page.find('div', class_='banner-dangerous').find('h1').text == 'We cannot print your letter'
+    assert page.find(
+        'div', class_='banner-dangerous').find('p').text == (
+        'The content appears outside the printable area on page 1 Files must meet our letter specification.'
+    )
     assert not page.find('button', {'type': 'submit'})
 
 
@@ -216,10 +233,12 @@ def test_post_upload_letter_shows_letter_preview_for_invalid_file(mocker, client
     mocker.patch('app.main.views.uploads.upload_letter_to_s3')
     mock_sanitise_response = Mock()
     mock_sanitise_response.raise_for_status.side_effect = RequestException(response=Mock(status_code=400))
+    mock_sanitise_response.json = lambda: {"message": "template preview error"}
     mocker.patch('app.main.views.uploads.sanitise_letter', return_value=mock_sanitise_response)
     mocker.patch('app.main.views.uploads.service_api_client.get_precompiled_template', return_value=letter_template)
     mocker.patch('app.main.views.uploads.get_letter_metadata', return_value={
-        'filename': 'tests/test_pdf_files/one_page_pdf.pdf', 'page_count': '1', 'status': 'invalid'})
+        'filename': 'tests/test_pdf_files/one_page_pdf.pdf', 'page_count': '1', 'status': 'invalid',
+        'message': 'template-preview-error'})
 
     with open('tests/test_pdf_files/one_page_pdf.pdf', 'rb') as file:
         page = client_request.post(
@@ -274,6 +293,7 @@ def test_uploaded_letter_preview(mocker, client_request):
         original_filename='my_letter.pdf',
         page_count=1,
         status='valid',
+        error={}
     )
 
     assert page.find('h1').text == 'my_letter.pdf'
@@ -334,7 +354,8 @@ def test_send_uploaded_letter_when_metadata_states_pdf_is_invalid(mocker, servic
     mock_send = mocker.patch('app.main.views.uploads.notification_api_client.send_precompiled_letter')
     mocker.patch(
         'app.main.views.uploads.get_letter_metadata',
-        return_value={'filename': 'my_file.pdf', 'page_count': '3', 'status': 'invalid'}
+        return_value={'filename': 'my_file.pdf', 'page_count': '3', 'status': 'invalid',
+                      'message': 'error', 'invalid_pages': '[1]'}
     )
 
     service_one['permissions'] = ['letter', 'upload_letters']