diff --git a/app/template/rest.py b/app/template/rest.py
index 61f07d105..e8fba9fab 100644
--- a/app/template/rest.py
+++ b/app/template/rest.py
@@ -245,11 +245,15 @@ def preview_letter_template_by_notification_id(service_id, notification_id, file
                 status_code=500
             )
 
-        content = base64.b64encode(pdf_file).decode('utf-8')
-        overlay = metadata.get("message") == "content-outside-printable-area"
         page_number = page if page else "1"
+        content = base64.b64encode(pdf_file).decode('utf-8')
+        content_outside_printable_area = metadata.get("message") == "content-outside-printable-area"
 
-        if overlay:
+        show_overlay_for_page = False
+        if content_outside_printable_area and page_number in metadata.get('invalid_pages', '[]'):
+            show_overlay_for_page = True
+
+        if show_overlay_for_page or (content_outside_printable_area and file_type == "pdf"):
             path = '/precompiled/overlay.{}'.format(file_type)
             query_string = '?page_number={}'.format(page_number) if file_type == 'png' else ''
             content = pdf_file
@@ -262,7 +266,7 @@ def preview_letter_template_by_notification_id(service_id, notification_id, file
         if file_type == 'png':
             try:
                 pdf_page = extract_page_from_pdf(BytesIO(pdf_file), int(page_number) - 1)
-                content = pdf_page if overlay else base64.b64encode(pdf_page).decode('utf-8')
+                content = pdf_page if show_overlay_for_page else base64.b64encode(pdf_page).decode('utf-8')
             except PdfReadError as e:
                 raise InvalidRequest(
                     'Error extracting requested page from PDF file for notification_id {} type {} {}'.format(
diff --git a/tests/app/template/test_rest.py b/tests/app/template/test_rest.py
index e9f6ea04d..ffe660cea 100644
--- a/tests/app/template/test_rest.py
+++ b/tests/app/template/test_rest.py
@@ -1143,23 +1143,27 @@ def test_preview_letter_template_precompiled_s3_error(
 
 
 @pytest.mark.parametrize(
-    "requested_page, filetype, message, expected_post_url",
+    "requested_page, message, expected_post_url",
     [
-        ("", 'png', "", 'precompiled-preview.png'),
-        ("1", 'png', "content-outside-printable-area", 'precompiled/overlay.png?page_number=1'),
-        ("2", 'png', "content-outside-printable-area", 'precompiled/overlay.png?page_number=2'),
-        ("3", 'png', "content-outside-printable-area", 'precompiled/overlay.png?page_number=3'),
-        ("", 'pdf', "content-outside-printable-area", 'precompiled/overlay.pdf')
+        # page defaults to 1, page is valid, no overlay shown
+        ("", "", 'precompiled-preview.png'),
+        # page is valid, no overlay shown
+        ("1", "", 'precompiled-preview.png'),
+        # page is invalid, overlay shown
+        ("1", "content-outside-printable-area", 'precompiled/overlay.png?page_number=1'),
+        # page is valid, no overlay shown
+        ("2", "content-outside-printable-area", 'precompiled-preview.png'),
+        # page is invalid, overlay shown
+        ("3", "content-outside-printable-area", 'precompiled/overlay.png?page_number=3'),
     ]
 )
-def test_preview_letter_template_precompiled_png_file_type_or_pdf_with_overlay(
+def test_preview_letter_template_precompiled_for_png_file_shows_overlay_where_appropriate(
         notify_api,
         client,
         admin_request,
         sample_service,
         mocker,
         requested_page,
-        filetype,
         message,
         expected_post_url,
 ):
@@ -1206,7 +1210,74 @@ def test_preview_letter_template_precompiled_png_file_type_or_pdf_with_overlay(
                 page=requested_page,
                 service_id=notification.service_id,
                 notification_id=notification.id,
-                file_type=filetype,
+                file_type="png",
+            )
+
+            with pytest.raises(ValueError):
+                mock_post.last_request.json()
+            assert mock_get_letter_pdf.called_once_with(notification)
+            assert base64.b64decode(response['content']) == expected_returned_content
+            assert response["metadata"] == metadata
+
+
+@pytest.mark.parametrize(
+    "invalid_pages",
+    [
+        "[1,3]",
+        "[2,4]",  # it shouldn't make a difference if the error was on the first page or not
+    ]
+)
+def test_preview_letter_template_precompiled_for_pdf_file_shows_overlay_if_content_outside_printable_area(
+        notify_api,
+        client,
+        admin_request,
+        sample_service,
+        mocker,
+        invalid_pages,
+):
+
+    template = create_template(sample_service,
+                               template_type='letter',
+                               template_name='Pre-compiled PDF',
+                               subject='Pre-compiled PDF',
+                               hidden=True)
+
+    notification = create_notification(template)
+
+    with set_config_values(notify_api, {
+        'TEMPLATE_PREVIEW_API_HOST': 'http://localhost/notifications-template-preview',
+        'TEMPLATE_PREVIEW_API_KEY': 'test-key'
+    }):
+        with requests_mock.Mocker() as request_mock:
+
+            pdf_content = b'\x00\x01'
+            expected_returned_content = b'\x00\x02'
+
+            metadata = {
+                "message": "content-outside-printable-area",
+                "invalid_pages": invalid_pages,
+                "page_count": "4"
+            }
+
+            mock_get_letter_pdf = mocker.patch(
+                'app.template.rest.get_letter_pdf_and_metadata',
+                return_value=(pdf_content, metadata)
+            )
+
+            mocker.patch('app.template.rest.extract_page_from_pdf', return_value=pdf_content)
+
+            mock_post = request_mock.post(
+                'http://localhost/notifications-template-preview/precompiled/overlay.pdf',
+                content=expected_returned_content,
+                headers={'X-pdf-page-count': '4'},
+                status_code=200
+            )
+
+            response = admin_request.get(
+                'template.preview_letter_template_by_notification_id',
+                service_id=notification.service_id,
+                notification_id=notification.id,
+                file_type="pdf",
             )
 
             with pytest.raises(ValueError):