diff --git a/starpunk/media.py b/starpunk/media.py
index a7c0c79..c4a6401 100644
--- a/starpunk/media.py
+++ b/starpunk/media.py
@@ -108,7 +108,23 @@ def validate_image(file_data: bytes, filename: str) -> Tuple[bytes, str, int, in
         # Re-open after verify (verify() closes the file)
         img = Image.open(io.BytesIO(file_data))
     except Exception as e:
-        raise ValueError(f"Invalid or corrupted image: {e}")
+        # v1.4.2: If Pillow can't open, try explicitly as HEIC
+        # iOS sometimes saves HEIC with .jpeg extension
+        if HEIC_SUPPORTED:
+            try:
+                heif_file = pillow_heif.read_heif(file_data)
+                img = Image.frombytes(
+                    heif_file.mode,
+                    heif_file.size,
+                    heif_file.data,
+                    "raw",
+                )
+                # Mark as HEIF so conversion happens below
+                img.format = 'HEIF'
+            except Exception:
+                raise ValueError(f"Invalid or corrupted image: {e}")
+        else:
+            raise ValueError(f"Invalid or corrupted image: {e}")
 
     # HEIC/HEIF conversion (v1.4.2)
     # HEIC cannot be displayed in browsers, convert to JPEG