diff --git a/backend/modules/fleet/tests/test_work_order_images_endpoint.py b/backend/modules/fleet/tests/test_work_order_images_endpoint.py
index cbfd21d..1c5ba37 100644
--- a/backend/modules/fleet/tests/test_work_order_images_endpoint.py
+++ b/backend/modules/fleet/tests/test_work_order_images_endpoint.py
@@ -252,6 +252,20 @@ class WorkOrderImagesEndpointTests(TestCase):
         self.assertIsNotNone(result)
         self.assertGreater(len(result.getvalue()), 0)
 
+    def test_compress_image_for_docx_handles_exif_orientation(self):
+        exif = Image.Exif()
+        exif[0x0112] = 6
+
+        file = BytesIO()
+        Image.new('RGB', (3000, 2000), color='green').save(file, format='JPEG', quality=85, exif=exif.tobytes())
+        file.seek(0)
+        uploaded = SimpleUploadedFile('rotated-phone.jpg', file.getvalue(), content_type='image/jpeg')
+
+        result = _compress_image_for_docx(uploaded)
+
+        self.assertIsNotNone(result)
+        self.assertGreater(len(result.getvalue()), 0)
+
     def test_work_order_related_tasks_queryset_excludes_other_work_orders_for_same_vehicle(self):
         other_work_order = WorkOrder.objects.create(
             vehicle=self.vehicle,
diff --git a/backend/modules/fleet/views.py b/backend/modules/fleet/views.py
index d39fb6b..24e77f7 100644
--- a/backend/modules/fleet/views.py
+++ b/backend/modules/fleet/views.py
@@ -14,7 +14,7 @@ from pathlib import Path
 from decimal import Decimal, InvalidOperation
 from django.contrib.auth import get_user_model
 
-from PIL import Image, UnidentifiedImageError
+from PIL import Image, ImageOps, UnidentifiedImageError
 from django.conf import settings
 from django.core.mail import EmailMessage
 from django.core.exceptions import ValidationError as DjangoValidationError
@@ -479,6 +479,7 @@ def _compress_image_for_pdf(image_field, max_width=800, quality=75):
     try:
         image_field.open('rb')
         with Image.open(image_field) as img:
+            img = ImageOps.exif_transpose(img)
             w, h = img.size
             if w * h > _COMPRESS_IMAGE_MAX_MEGAPIXELS * 1_000_000:
                 return None
@@ -508,6 +509,7 @@ def _compress_image_for_docx(image_field, max_width=800, quality=80):
     try:
         image_field.open('rb')
         with Image.open(image_field) as img:
+            img = ImageOps.exif_transpose(img)
             w, h = img.size
             if w * h > _COMPRESS_IMAGE_MAX_MEGAPIXELS * 1_000_000:
                 return None