diff --git a/.gitignore b/.gitignore
index 6e3390e3a..7bd8f44b7 100644
--- a/.gitignore
+++ b/.gitignore
@@ -146,4 +146,5 @@ data/
 sessions/
 backups/
 uploads/
+.uploads/
 config/mcp.json
\ No newline at end of file
diff --git a/src/bot/features/file_handler.py b/src/bot/features/file_handler.py
index 5454c0651..16dcc4abf 100644
--- a/src/bot/features/file_handler.py
+++ b/src/bot/features/file_handler.py
@@ -14,8 +14,9 @@
 import zipfile
 from collections import defaultdict
 from dataclasses import dataclass
+from datetime import UTC, datetime
 from pathlib import Path
-from typing import Dict, List
+from typing import Dict, List, Optional
 
 from telegram import Document
 
@@ -131,12 +132,23 @@ def __init__(self, config: Settings, security: SecurityValidator):
         }
 
     async def handle_document_upload(
-        self, document: Document, user_id: int, context: str = ""
+        self,
+        document: Document,
+        user_id: int,
+        context: str = "",
+        current_dir: Optional[Path] = None,
     ) -> ProcessedFile:
-        """Process uploaded document"""
+        """Process uploaded document.
+
+        current_dir is used by the "document" branch to persist binary files
+        (PDF, etc.) into <current_dir>/.uploads/ where Claude can read them via
+        the Read tool. Defaults to approved_directory when omitted.
+        """
 
         # Download file
         file_path = await self._download_file(document)
+        original_name = document.file_name or file_path.name
+        persist_root = current_dir or Path(self.config.approved_directory)
 
         try:
             # Detect file type
@@ -145,6 +157,10 @@ async def handle_document_upload(
             # Process based on type
             if file_type == "archive":
                 return await self._process_archive(file_path, context)
+            elif file_type == "document":
+                return await self._process_document_file(
+                    file_path, context, persist_root, original_name
+                )
             elif file_type == "code":
                 return await self._process_code_file(file_path, context)
             elif file_type == "text":
@@ -153,7 +169,8 @@ async def handle_document_upload(
                 raise ValueError(f"Unsupported file type: {file_type}")
 
         finally:
-            # Cleanup
+            # Cleanup temp download. Document branch has already copied the
+            # payload to <persist_root>/.uploads/ — that copy survives.
             file_path.unlink(missing_ok=True)
 
     async def _download_file(self, document: Document) -> Path:
@@ -170,6 +187,20 @@ async def _download_file(self, document: Document) -> Path:
 
         return file_path
 
+    # Binary document formats: saved to disk for Claude to read via the
+    # appropriate tool (Read for PDF; Bash with pandoc/python-docx/openpyxl/
+    # unzip for Office and OpenDocument formats).
+    document_extensions = {
+        ".pdf",
+        ".docx",
+        ".xlsx",
+        ".pptx",
+        ".odt",
+        ".ods",
+        ".odp",
+        ".rtf",
+    }
+
     def _detect_file_type(self, file_path: Path) -> str:
         """Detect file type based on extension and content"""
         ext = file_path.suffix.lower()
@@ -178,6 +209,10 @@ def _detect_file_type(self, file_path: Path) -> str:
         if ext in {".zip", ".tar", ".gz", ".bz2", ".xz", ".7z"}:
             return "archive"
 
+        # Check if document (binary — saved to disk, read by Claude tools)
+        if ext in self.document_extensions:
+            return "document"
+
         # Check if code
         if ext in self.code_extensions:
             return "code"
@@ -283,6 +318,46 @@ async def _process_code_file(self, file_path: Path, context: str) -> ProcessedFi
             },
         )
 
+    async def _process_document_file(
+        self,
+        file_path: Path,
+        context: str,
+        persist_root: Path,
+        original_name: str,
+    ) -> ProcessedFile:
+        """Persist a binary document to <persist_root>/.uploads/ and return a
+        prompt telling Claude to read it via the Read tool.
+
+        The copy survives this call (the caller's `finally` cleans up only the
+        temp download), so Claude can read the file during the conversation and
+        even in follow-up turns.
+        """
+        uploads_dir = persist_root / ".uploads"
+        uploads_dir.mkdir(parents=True, exist_ok=True)
+
+        timestamp = datetime.now(UTC).strftime("%Y%m%d-%H%M%S-%f")[:-3]
+        safe_name = f"{timestamp}-{original_name}"
+        target = uploads_dir / safe_name
+
+        shutil.copy2(file_path, target)
+
+        prompt = (
+            f"{context or 'User uploaded a file:'}\n\n"
+            f"Path: `{target}`\n\n"
+            "Read the file using the appropriate tool for its format "
+            "and answer the user's question."
+        )
+
+        return ProcessedFile(
+            type="document",
+            prompt=prompt,
+            metadata={
+                "saved_path": str(target),
+                "original_name": original_name,
+                "size": target.stat().st_size,
+            },
+        )
+
     async def _process_text_file(self, file_path: Path, context: str) -> ProcessedFile:
         """Process text file"""
         content = file_path.read_text(encoding="utf-8", errors="ignore")
diff --git a/src/bot/handlers/message.py b/src/bot/handlers/message.py
index bbd240840..f73efa050 100644
--- a/src/bot/handlers/message.py
+++ b/src/bot/handlers/message.py
@@ -1,6 +1,7 @@
 """Message handlers for non-command inputs."""
 
 import asyncio
+from pathlib import Path
 from typing import Optional
 
 import structlog
@@ -725,6 +726,13 @@ async def handle_document(update: Update, context: ContextTypes.DEFAULT_TYPE) ->
             parse_mode="HTML",
         )
 
+        # current_dir is needed by the document branch of file_handler to
+        # persist binary uploads (PDF etc.) into <current_dir>/.uploads/ where
+        # Claude can reach them via its Read tool.
+        current_dir = Path(
+            context.user_data.get("current_directory", settings.approved_directory)
+        )
+
         # Check if enhanced file handler is available
         features = context.bot_data.get("features")
         file_handler = features.get_file_handler() if features else None
@@ -736,6 +744,7 @@ async def handle_document(update: Update, context: ContextTypes.DEFAULT_TYPE) ->
                     document,
                     user_id,
                     update.message.caption or "Please review this file:",
+                    current_dir=current_dir,
                 )
                 prompt = processed_file.prompt
 
@@ -781,6 +790,7 @@ async def handle_document(update: Update, context: ContextTypes.DEFAULT_TYPE) ->
                     "• Source code files (.py, .js, .ts, etc.)\n"
                     "• Text files (.txt, .md)\n"
                     "• Configuration files (.json, .yaml, .toml)\n"
+                    "• Documents (.pdf)\n"
                     "• Documentation files",
                     parse_mode="HTML",
                 )
@@ -805,10 +815,7 @@ async def handle_document(update: Update, context: ContextTypes.DEFAULT_TYPE) ->
             )
             return
 
-        # Get current directory and session
-        current_dir = context.user_data.get(
-            "current_directory", settings.approved_directory
-        )
+        # current_dir was already resolved above for the file_handler call.
         session_id = context.user_data.get("claude_session_id")
 
         # Process with Claude
diff --git a/src/bot/orchestrator.py b/src/bot/orchestrator.py
index 6d9719f0d..b71e7a33d 100644
--- a/src/bot/orchestrator.py
+++ b/src/bot/orchestrator.py
@@ -1192,6 +1192,13 @@ async def agentic_document(
         await chat.send_action("typing")
         progress_msg = await update.message.reply_text("Working...")
 
+        # current_dir is needed by the document branch of file_handler to persist
+        # binary uploads (PDF etc.) into <current_dir>/.uploads/ where Claude
+        # can reach them via its Read tool.
+        current_dir = Path(
+            context.user_data.get("current_directory", self.settings.approved_directory)
+        )
+
         # Try enhanced file handler, fall back to basic
         features = context.bot_data.get("features")
         file_handler = features.get_file_handler() if features else None
@@ -1203,6 +1210,7 @@ async def agentic_document(
                     document,
                     user_id,
                     update.message.caption or "Please review this file:",
+                    current_dir=current_dir,
                 )
                 prompt = processed_file.prompt
             except Exception:
@@ -1233,10 +1241,6 @@ async def agentic_document(
                 "Claude integration not available. Check configuration."
             )
             return
-
-        current_dir = context.user_data.get(
-            "current_directory", self.settings.approved_directory
-        )
         session_id = context.user_data.get("claude_session_id")
 
         # Check if /new was used — skip auto-resume for this first message.
diff --git a/src/security/validators.py b/src/security/validators.py
index 381ba321d..9992b5be2 100644
--- a/src/security/validators.py
+++ b/src/security/validators.py
@@ -86,6 +86,23 @@ class SecurityValidator:
         ".vue",
         ".svelte",
         ".lock",
+        # Text-compatible document formats (UTF-8, handled inline)
+        ".csv",
+        ".tsv",
+        ".log",
+        ".ics",
+        ".eml",
+        # Binary document formats (persisted to .uploads/ for Claude to read
+        # via the appropriate tool — Read for PDF, Bash with converters for
+        # Office and OpenDocument formats)
+        ".pdf",
+        ".docx",
+        ".xlsx",
+        ".pptx",
+        ".odt",
+        ".ods",
+        ".odp",
+        ".rtf",
     }
 
     # Forbidden filenames and patterns
diff --git a/tests/unit/test_bot/test_file_handler.py b/tests/unit/test_bot/test_file_handler.py
new file mode 100644
index 000000000..1beaf81bd
--- /dev/null
+++ b/tests/unit/test_bot/test_file_handler.py
@@ -0,0 +1,143 @@
+"""Tests for the FileHandler document branch."""
+
+import tempfile
+from pathlib import Path
+from unittest.mock import AsyncMock, MagicMock
+
+import pytest
+
+from src.bot.features.file_handler import FileHandler
+from src.config import create_test_config
+
+
+@pytest.fixture
+def tmp_dir():
+    with tempfile.TemporaryDirectory() as d:
+        yield Path(d)
+
+
+@pytest.fixture
+def file_handler(tmp_dir):
+    settings = create_test_config(approved_directory=str(tmp_dir))
+    security = MagicMock()
+    return FileHandler(settings, security)
+
+
+@pytest.mark.parametrize(
+    "filename",
+    [
+        "report.pdf",
+        "contract.docx",
+        "budget.xlsx",
+        "deck.pptx",
+        "notes.odt",
+        "letter.rtf",
+    ],
+)
+def test_detect_file_type_binary_document_formats_return_document(
+    file_handler, filename
+):
+    assert file_handler._detect_file_type(Path(filename)) == "document"
+
+
+def test_detect_file_type_unknown_binary_stays_binary(file_handler, tmp_dir):
+    # A file with unknown extension + non-UTF-8 bytes should not become "document"
+    # — only whitelisted extensions in `document_extensions` do.
+    blob = tmp_dir / "mystery.blob"
+    blob.write_bytes(b"\xff\xfe\x00\x01binarydata")
+    assert file_handler._detect_file_type(blob) == "binary"
+
+
+def test_detect_file_type_csv_goes_through_text_branch(file_handler, tmp_dir):
+    """CSV and similar UTF-8 tabular formats aren't in `document_extensions` —
+    they fall through to the text branch (inline content in the prompt)."""
+    csv_file = tmp_dir / "data.csv"
+    csv_file.write_text("a,b,c\n1,2,3\n", encoding="utf-8")
+    assert file_handler._detect_file_type(csv_file) == "text"
+
+
+async def test_process_document_file_copies_and_builds_prompt(file_handler, tmp_dir):
+    """_process_document_file copies PDF to <persist_root>/.uploads/ with a
+    timestamp prefix, leaves it in place, and embeds the absolute path in
+    the returned prompt.
+    """
+    source = tmp_dir / "src_ticket.pdf"
+    source.write_bytes(b"%PDF-1.4\nSMOKE-TOKEN-42\n%%EOF\n")
+
+    result = await file_handler._process_document_file(
+        source,
+        context="please summarize",
+        persist_root=tmp_dir,
+        original_name="ticket.pdf",
+    )
+
+    uploads_dir = tmp_dir / ".uploads"
+    saved_files = list(uploads_dir.glob("*-ticket.pdf"))
+    assert len(saved_files) == 1
+    assert saved_files[0].read_bytes() == source.read_bytes()
+
+    assert result.type == "document"
+    assert str(saved_files[0]) in result.prompt
+    assert "please summarize" in result.prompt
+    assert result.metadata["saved_path"] == str(saved_files[0])
+    assert result.metadata["original_name"] == "ticket.pdf"
+    assert result.metadata["size"] == source.stat().st_size
+
+
+async def test_handle_document_upload_pdf_end_to_end(file_handler, tmp_dir):
+    """handle_document_upload routes .pdf to the document branch and persists
+    the file into current_dir/.uploads/."""
+    pdf_bytes = b"%PDF-1.4\nSMOKE\n%%EOF\n"
+
+    async def fake_download(target_path):
+        Path(target_path).write_bytes(pdf_bytes)
+
+    tg_file = MagicMock()
+    tg_file.download_to_drive = AsyncMock(side_effect=fake_download)
+
+    document = MagicMock()
+    document.file_name = "ticket.pdf"
+    document.get_file = AsyncMock(return_value=tg_file)
+
+    # Use a subdirectory as current_dir to verify the handler honours it over
+    # the default approved_directory.
+    current_dir = tmp_dir / "project"
+    current_dir.mkdir()
+
+    result = await file_handler.handle_document_upload(
+        document,
+        user_id=1,
+        context="summarize",
+        current_dir=current_dir,
+    )
+
+    uploads_dir = current_dir / ".uploads"
+    saved_files = list(uploads_dir.glob("*-ticket.pdf"))
+    assert len(saved_files) == 1
+    assert saved_files[0].read_bytes() == pdf_bytes
+    assert result.type == "document"
+    assert str(saved_files[0]) in result.prompt
+
+
+async def test_handle_document_upload_defaults_to_approved_directory(
+    file_handler, tmp_dir
+):
+    """Without explicit current_dir, document branch falls back to
+    approved_directory — backward-compatible behaviour."""
+    pdf_bytes = b"%PDF-1.4\nfallback\n%%EOF\n"
+
+    async def fake_download(target_path):
+        Path(target_path).write_bytes(pdf_bytes)
+
+    tg_file = MagicMock()
+    tg_file.download_to_drive = AsyncMock(side_effect=fake_download)
+
+    document = MagicMock()
+    document.file_name = "fallback.pdf"
+    document.get_file = AsyncMock(return_value=tg_file)
+
+    result = await file_handler.handle_document_upload(document, user_id=1, context="")
+
+    saved_files = list((tmp_dir / ".uploads").glob("*-fallback.pdf"))
+    assert len(saved_files) == 1
+    assert result.type == "document"
diff --git a/tests/unit/test_security/test_validators.py b/tests/unit/test_security/test_validators.py
index a15f5c31a..a5575f041 100644
--- a/tests/unit/test_security/test_validators.py
+++ b/tests/unit/test_security/test_validators.py
@@ -139,6 +139,12 @@ def test_filename_validation_valid(self, validator):
             "style.css",
             "data.sql",
             "build.sh",
+            "report.pdf",
+            "contract.docx",
+            "budget.xlsx",
+            "data.csv",
+            "access.log",
+            "invite.ics",
         ]
 
         for filename in valid_filenames:
@@ -146,6 +152,12 @@ def test_filename_validation_valid(self, validator):
             assert valid is True
             assert error is None
 
+    def test_filename_pdf_exe_suffix_blocked(self, validator):
+        """Regression: `.pdf.exe` trap name is still blocked by dangerous patterns."""
+        valid, error = validator.validate_filename("ticket.pdf.exe")
+        assert valid is False
+        assert "not allowed" in error
+
     def test_filename_validation_invalid_extensions(self, validator):
         """Test rejection of invalid file extensions."""
         invalid_filenames = [