diff --git a/surfsense_backend/app/tasks/document_processors/file_processors.py b/surfsense_backend/app/tasks/document_processors/file_processors.py
index 596cd9830..307e09897 100644
--- a/surfsense_backend/app/tasks/document_processors/file_processors.py
+++ b/surfsense_backend/app/tasks/document_processors/file_processors.py
@@ -2,11 +2,14 @@
 File document processors for different ETL services (Unstructured, LlamaCloud, Docling).
 """
 
+import asyncio
 import contextlib
 import logging
+import ssl
 import warnings
 from logging import ERROR, getLogger
 
+import httpx
 from fastapi import HTTPException
 from langchain_core.documents import Document as LangChainDocument
 from litellm import atranscription
@@ -32,6 +35,123 @@ from .base import (
 from .markdown_processor import add_received_markdown_file_document
 
 
+# Constants for LlamaCloud retry configuration
+LLAMACLOUD_MAX_RETRIES = 3
+LLAMACLOUD_BASE_DELAY = 5  # Base delay in seconds for exponential backoff
+LLAMACLOUD_RETRYABLE_EXCEPTIONS = (
+    ssl.SSLError,
+    httpx.ConnectError,
+    httpx.ConnectTimeout,
+    httpx.ReadTimeout,
+    httpx.WriteTimeout,
+    ConnectionError,
+    TimeoutError,
+)
+
+
+async def parse_with_llamacloud_retry(
+    file_path: str,
+    estimated_pages: int,
+    task_logger: TaskLoggingService | None = None,
+    log_entry: Log | None = None,
+):
+    """
+    Parse a file with LlamaCloud with retry logic for transient SSL/connection errors.
+
+    Args:
+        file_path: Path to the file to parse
+        estimated_pages: Estimated number of pages for timeout calculation
+        task_logger: Optional task logger for progress updates
+        log_entry: Optional log entry for progress updates
+
+    Returns:
+        LlamaParse result object
+
+    Raises:
+        Exception: If all retries fail
+    """
+    from llama_cloud_services import LlamaParse
+    from llama_cloud_services.parse.utils import ResultType
+
+    # Calculate timeouts based on estimated pages
+    # Base timeout of 300 seconds + 30 seconds per page for large documents
+    base_timeout = 300
+    per_page_timeout = 30
+    job_timeout = base_timeout + (estimated_pages * per_page_timeout)
+
+    # Create custom httpx client with larger timeouts for file uploads
+    # The SSL error often occurs during large file uploads, so we need generous timeouts
+    custom_timeout = httpx.Timeout(
+        connect=60.0,  # 60 seconds to establish connection
+        read=300.0,  # 5 minutes to read response
+        write=300.0,  # 5 minutes to write/upload (important for large files)
+        pool=60.0,  # 60 seconds to acquire connection from pool
+    )
+
+    last_exception = None
+
+    for attempt in range(1, LLAMACLOUD_MAX_RETRIES + 1):
+        try:
+            # Create a fresh httpx client for each attempt
+            async with httpx.AsyncClient(timeout=custom_timeout) as custom_client:
+                # Create LlamaParse parser instance with optimized settings
+                parser = LlamaParse(
+                    api_key=app_config.LLAMA_CLOUD_API_KEY,
+                    num_workers=1,  # Use single worker for file processing
+                    verbose=True,
+                    language="en",
+                    result_type=ResultType.MD,
+                    # Timeout settings for large files
+                    max_timeout=max(2000, job_timeout),  # Overall max timeout
+                    job_timeout_in_seconds=job_timeout,
+                    job_timeout_extra_time_per_page_in_seconds=per_page_timeout,
+                    # Use our custom client with larger timeouts
+                    custom_client=custom_client,
+                )
+
+                # Parse the file asynchronously
+                result = await parser.aparse(file_path)
+                return result
+
+        except LLAMACLOUD_RETRYABLE_EXCEPTIONS as e:
+            last_exception = e
+            error_type = type(e).__name__
+
+            if attempt < LLAMACLOUD_MAX_RETRIES:
+                # Calculate exponential backoff delay
+                delay = LLAMACLOUD_BASE_DELAY * (2 ** (attempt - 1))
+
+                if task_logger and log_entry:
+                    await task_logger.log_task_progress(
+                        log_entry,
+                        f"LlamaCloud upload failed (attempt {attempt}/{LLAMACLOUD_MAX_RETRIES}), retrying in {delay}s",
+                        {
+                            "error_type": error_type,
+                            "error_message": str(e)[:200],
+                            "attempt": attempt,
+                            "retry_delay": delay,
+                        },
+                    )
+                else:
+                    logging.warning(
+                        f"LlamaCloud upload failed (attempt {attempt}/{LLAMACLOUD_MAX_RETRIES}): {error_type}. "
+                        f"Retrying in {delay}s..."
+                    )
+
+                await asyncio.sleep(delay)
+            else:
+                logging.error(
+                    f"LlamaCloud upload failed after {LLAMACLOUD_MAX_RETRIES} attempts: {error_type} - {e}"
+                )
+
+        except Exception:
+            # Non-retryable exception, raise immediately
+            raise
+
+    # All retries exhausted
+    raise last_exception or RuntimeError("LlamaCloud parsing failed after all retries")
+
+
 async def add_received_file_document_using_unstructured(
     session: AsyncSession,
     file_name: str,
@@ -819,24 +939,18 @@ async def process_file_in_background(
                         "file_type": "document",
                         "etl_service": "LLAMACLOUD",
                         "processing_stage": "parsing",
+                        "estimated_pages": estimated_pages_before,
                     },
                 )
 
-                from llama_cloud_services import LlamaParse
-                from llama_cloud_services.parse.utils import ResultType
-
-                # Create LlamaParse parser instance
-                parser = LlamaParse(
-                    api_key=app_config.LLAMA_CLOUD_API_KEY,
-                    num_workers=1,  # Use single worker for file processing
-                    verbose=True,
-                    language="en",
-                    result_type=ResultType.MD,
+                # Parse file with retry logic for SSL/connection errors (common with large files)
+                result = await parse_with_llamacloud_retry(
+                    file_path=file_path,
+                    estimated_pages=estimated_pages_before,
+                    task_logger=task_logger,
+                    log_entry=log_entry,
                 )
 
-                # Parse the file asynchronously
-                result = await parser.aparse(file_path)
-
                 # Clean up the temp file
                 import os