diff --git a/backend/open_webui/retrieval/loaders/main.py b/backend/open_webui/retrieval/loaders/main.py
index f84b2a2b1b..1a5185d02a 100644
--- a/backend/open_webui/retrieval/loaders/main.py
+++ b/backend/open_webui/retrieval/loaders/main.py
@@ -13,7 +13,6 @@ from langchain_community.document_loaders import (
     BSHTMLLoader,
     CSVLoader,
     Docx2txtLoader,
-    PyPDFLoader,
     TextLoader,
 )
 from langchain_core.documents import Document
@@ -28,6 +27,7 @@ from open_webui.retrieval.loaders.external_document import ExternalDocumentLoade
 from open_webui.retrieval.loaders.mineru import MinerULoader
 from open_webui.retrieval.loaders.mistral import MistralLoader
 from open_webui.retrieval.loaders.paddleocr_vl import PADDLEOCR_VL_SUPPORTED_EXTENSIONS, PaddleOCRVLLoader
+from open_webui.retrieval.loaders.pdf import PyPDFLoaderWithSafeImages
 from open_webui.utils.headers import get_user_groups_for_custom_headers
 from open_webui.utils.json_codec import JSONCodec
 
@@ -667,7 +667,7 @@ class Loader:
             )
         else:
             if file_ext == 'pdf':
-                loader = PyPDFLoader(
+                loader = PyPDFLoaderWithSafeImages(
                     file_path,
                     extract_images=self.kwargs.get('PDF_EXTRACT_IMAGES'),
                     mode=self.kwargs.get('PDF_LOADER_MODE', 'page'),
diff --git a/backend/open_webui/retrieval/loaders/pdf.py b/backend/open_webui/retrieval/loaders/pdf.py
new file mode 100644
index 0000000000..0dc2a22133
--- /dev/null
+++ b/backend/open_webui/retrieval/loaders/pdf.py
@@ -0,0 +1,70 @@
+import io
+import logging
+from typing import Literal
+
+from langchain_community.document_loaders import PyPDFLoader
+from langchain_community.document_loaders.parsers.pdf import PyPDFParser
+from langchain_core.document_loaders import Blob
+from PIL import Image
+from pypdf import PageObject
+from pypdf.generic import StreamObject
+
+log = logging.getLogger(__name__)
+
+
+def _is_cmyk_jpeg(image_stream: StreamObject) -> bool:
+    """True when the image is a CMYK JPEG whose data pypdf will hand back inverted."""
+    filters = image_stream['/Filter'] if '/Filter' in image_stream else None
+    if (filters[-1] if isinstance(filters, list) else filters) != '/DCTDecode':
+        return False
+    return Image.open(io.BytesIO(image_stream.get_data())).mode == 'CMYK'
+
+
+class PyPDFParserWithSafeImages(PyPDFParser):
+    """PyPDFParser that lets pypdf decode page images instead of reading /Filter itself."""
+
+    def extract_images_from_page(self, page: PageObject) -> str:
+        if not self.images_parser:
+            return ''
+
+        page.inline_images = {}
+        try:
+            images = page.images[:]
+        except Exception as e:
+            log.warning('Skipping images on PDF page: %s', e)
+            return ''
+
+        image_texts = []
+        for index in range(len(images)):
+            try:
+                image_file = images[index]
+                image_stream = image_file.indirect_reference.get_object()
+                image = image_file.image
+                # pypdf re-inverts CMYK JPEGs that PIL already un-inverted, and an /SMask makes that unrecoverable
+                if _is_cmyk_jpeg(image_stream):
+                    image = Image.open(io.BytesIO(image_stream.get_data()))
+
+                png_bytes = io.BytesIO()
+                image.convert('RGB').save(png_bytes, format='PNG')
+            except Exception as e:
+                log.warning('Skipping unreadable image %s on PDF page: %s', index, e)
+                continue
+
+            blob = Blob.from_data(png_bytes.getvalue(), mime_type='image/png')
+            text = next(self.images_parser.lazy_parse(blob)).page_content
+            if text:
+                image_texts.append(text)
+
+        if not image_texts:
+            return ''
+        return '\n\n' + '\n'.join(image_texts) + '\n\n'
+
+
+class PyPDFLoaderWithSafeImages(PyPDFLoader):
+    """Loads a PDF with pypdf, tolerating images it cannot decode instead of failing the document."""
+
+    def __init__(
+        self, file_path: str, *, extract_images: bool = False, mode: Literal['single', 'page'] = 'page'
+    ) -> None:
+        super().__init__(file_path, extract_images=extract_images, mode=mode)
+        self.parser = PyPDFParserWithSafeImages(extract_images=extract_images, mode=mode)