diff --git a/control-pipeline/scripts/reingest_d5.py b/control-pipeline/scripts/reingest_d5.py
index cd40b5f..31d880a 100644
--- a/control-pipeline/scripts/reingest_d5.py
+++ b/control-pipeline/scripts/reingest_d5.py
@@ -44,7 +44,7 @@ from reingest_d5_config import (
 logging.basicConfig(level=logging.INFO, format="%(asctime)s %(levelname)s %(message)s")
 logger = logging.getLogger("d5-reingest")
 
-UPLOAD_TIMEOUT = httpx.Timeout(timeout=1800.0, connect=30.0)
+UPLOAD_TIMEOUT = httpx.Timeout(timeout=3600.0, connect=30.0)
 SCROLL_TIMEOUT = httpx.Timeout(timeout=60.0, connect=10.0)
 
 
diff --git a/embedding-service/main.py b/embedding-service/main.py
index 86f733d..5124881 100644
--- a/embedding-service/main.py
+++ b/embedding-service/main.py
@@ -750,6 +750,12 @@ def detect_pdf_backends() -> List[str]:
     except ImportError:
         pass
 
+    try:
+        import pdfplumber  # noqa: F401
+        available.append("pdfplumber")
+    except ImportError:
+        pass
+
     try:
         from pypdf import PdfReader  # noqa: F401
         available.append("pypdf")
@@ -815,8 +821,32 @@ def extract_pdf_unstructured(pdf_content: bytes) -> ExtractPDFResponse:
             pass
 
 
+def extract_pdf_pdfplumber(pdf_content: bytes) -> ExtractPDFResponse:
+    """Extract PDF using pdfplumber (best for multi-column EU regulation PDFs)."""
+    import io
+    import pdfplumber
+
+    pdf_file = io.BytesIO(pdf_content)
+    text_parts = []
+    page_count = 0
+
+    with pdfplumber.open(pdf_file) as pdf:
+        page_count = len(pdf.pages)
+        for page in pdf.pages:
+            text = page.extract_text(x_tolerance=2, y_tolerance=3)
+            if text:
+                text_parts.append(text)
+
+    return ExtractPDFResponse(
+        text="\n\n".join(text_parts),
+        backend_used="pdfplumber",
+        pages=page_count,
+        table_count=0,
+    )
+
+
 def extract_pdf_pypdf(pdf_content: bytes) -> ExtractPDFResponse:
-    """Extract PDF using pypdf."""
+    """Extract PDF using pypdf (fallback)."""
     import io
     from pypdf import PdfReader
 
@@ -1039,11 +1069,19 @@ async def extract_pdf(file: UploadFile = File(...)):
 
     backend = config.PDF_EXTRACTION_BACKEND
     if backend == "auto":
-        backend = "unstructured" if "unstructured" in available else "pypdf"
+        # Prefer: unstructured > pdfplumber > pypdf
+        if "unstructured" in available:
+            backend = "unstructured"
+        elif "pdfplumber" in available:
+            backend = "pdfplumber"
+        else:
+            backend = "pypdf"
 
     try:
         if backend == "unstructured" and "unstructured" in available:
             return extract_pdf_unstructured(pdf_content)
+        elif backend == "pdfplumber" and "pdfplumber" in available:
+            return extract_pdf_pdfplumber(pdf_content)
         elif "pypdf" in available:
             return extract_pdf_pypdf(pdf_content)
         else:
diff --git a/embedding-service/requirements.txt b/embedding-service/requirements.txt
index 2d11c24..68b1442 100644
--- a/embedding-service/requirements.txt
+++ b/embedding-service/requirements.txt
@@ -14,6 +14,7 @@ sentence-transformers>=2.2.0
 # PDF Extraction
 unstructured>=0.12.0
 pypdf>=4.0.0
+pdfplumber>=0.11.0
 python-magic>=0.4.27
 
 # HTTP Client (for OpenAI/Cohere API calls)