diff --git a/app/main/views/send.py b/app/main/views/send.py
index 8e62e4137..36a43b9c0 100644
--- a/app/main/views/send.py
+++ b/app/main/views/send.py
@@ -22,6 +22,7 @@ from notifications_utils.recipients import (
 from orderedset import OrderedSet
 from werkzeug.routing import RequestRedirect
 from xlrd.biffh import XLRDError
+from xlrd.xldate import XLDateError
 
 from app import (
     current_service,
@@ -137,6 +138,13 @@ def send_messages(service_id, template_id):
             flash('Couldn’t read {}. Try using a different file format.'.format(
                 form.file.data.filename
             ))
+        except (XLDateError):
+            flash((
+                '{} contains numbers or dates that Notify can’t understand. '
+                'Try formatting all columns as ‘text’ or export your file as CSV.'
+            ).format(
+                form.file.data.filename
+            ))
 
     column_headings = first_column_headings[template.template_type] + list(template.placeholders)
 
diff --git a/tests/app/main/views/test_send.py b/tests/app/main/views/test_send.py
index 4f94b3b32..3554a115d 100644
--- a/tests/app/main/views/test_send.py
+++ b/tests/app/main/views/test_send.py
@@ -5,6 +5,7 @@ from glob import glob
 from io import BytesIO
 from itertools import repeat
 from os import path
+from zipfile import BadZipFile
 
 import pytest
 from bs4 import BeautifulSoup
@@ -37,6 +38,13 @@ from tests.conftest import (
     no_sms_senders,
     normalize_spaces,
 )
+from xlrd.biffh import XLRDError
+from xlrd.xldate import (
+    XLDateAmbiguous,
+    XLDateError,
+    XLDateNegative,
+    XLDateTooLarge,
+)
 
 template_types = ['email', 'sms']
 
@@ -278,6 +286,7 @@ def test_upload_files_in_different_formats(
             data={'file': (BytesIO(uploaded.read()), filename)},
             content_type='multipart/form-data'
         )
+        page = BeautifulSoup(response.data.decode('utf-8'), 'html.parser')
 
     if acceptable_file:
         assert mock_s3_upload.call_args[0][1]['data'].strip() == (
@@ -288,9 +297,64 @@ def test_upload_files_in_different_formats(
         )
     else:
         assert not mock_s3_upload.called
-        assert (
+        assert normalize_spaces(page.select_one('.banner-dangerous').text) == (
             'Couldn’t read {}. Try using a different file format.'.format(filename)
-        ) in response.get_data(as_text=True)
+        )
+
+
+@pytest.mark.parametrize('exception, expected_error_message', [
+    (partial(UnicodeDecodeError, 'codec', b'', 1, 2, 'reason'), (
+        'Couldn’t read example.xlsx. Try using a different file format.'
+    )),
+    (BadZipFile, (
+        'Couldn’t read example.xlsx. Try using a different file format.'
+    )),
+    (XLRDError, (
+        'Couldn’t read example.xlsx. Try using a different file format.'
+    )),
+    (XLDateError, (
+        'example.xlsx contains numbers or dates that Notify can’t understand. '
+        'Try formatting all columns as ‘text’ or export your file as CSV.'
+    )),
+    (XLDateNegative, (
+        'example.xlsx contains numbers or dates that Notify can’t understand. '
+        'Try formatting all columns as ‘text’ or export your file as CSV.'
+    )),
+    (XLDateAmbiguous, (
+        'example.xlsx contains numbers or dates that Notify can’t understand. '
+        'Try formatting all columns as ‘text’ or export your file as CSV.'
+    )),
+    (XLDateTooLarge, (
+        'example.xlsx contains numbers or dates that Notify can’t understand. '
+        'Try formatting all columns as ‘text’ or export your file as CSV.'
+    )),
+])
+def test_shows_error_if_parsing_exception(
+    logged_in_client,
+    mocker,
+    mock_get_service_template,
+    exception,
+    expected_error_message,
+):
+
+    def _raise_exception_or_partial_exception(file_content, filename):
+        raise exception()
+
+    mocker.patch(
+        'app.main.views.send.Spreadsheet.from_file',
+        side_effect=_raise_exception_or_partial_exception
+    )
+
+    response = logged_in_client.post(
+        url_for('main.send_messages', service_id=SERVICE_ONE_ID, template_id=fake_uuid),
+        data={'file': (BytesIO(b'example'), 'example.xlsx')},
+        content_type='multipart/form-data'
+    )
+    page = BeautifulSoup(response.data.decode('utf-8'), 'html.parser')
+
+    assert normalize_spaces(page.select_one('.banner-dangerous').text) == (
+        expected_error_message
+    )
 
 
 def test_upload_csvfile_with_errors_shows_check_page_with_errors(