diff --git a/pyproject.toml b/pyproject.toml
index c302e6a..7e26f72 100644
--- a/pyproject.toml
+++ b/pyproject.toml
@@ -21,5 +21,5 @@ dev = [
 requires = ["setuptools>=61.0"]
 build-backend = "setuptools.build_meta"
 
-[tool.uv]
-python-version = "3.11"
+[tool.setuptools]
+py-modules = ["server"]
diff --git a/server.py b/server.py
index b2182b4..280c912 100644
--- a/server.py
+++ b/server.py
@@ -1,10 +1,13 @@
 import os
 import json
 import logging
+import mimetypes
+import contextlib
 from typing import Any
 import httpx
 from fastmcp import FastMCP
 from starlette.applications import Starlette
+from starlette.requests import Request
 from starlette.responses import JSONResponse
 from starlette.routing import Route, Mount
 from dotenv import load_dotenv
@@ -491,6 +494,18 @@ Delete attachment. Params: id (required)
 ### attachments.redirect
 Get attachment URL. Params: id (required)
 
+### Custom HTTP Gateway Upload
+Rather than manually performing the multi-step attachments.create + PUT process, you can stream files directly through the MCP server's built-in HTTP streaming gateway:
+- **Endpoint**: `POST /upload`
+- **Query Parameters**:
+  - `documentId` (required): The UUID of the destination Outline document.
+  - `name` (required): The filename of the attachment.
+- **Headers**:
+  - `Content-Length` (required): Total size of the file in bytes.
+  - `Content-Type` (optional): The MIME type of the file (auto-detected if omitted).
+- **Body**: Raw binary stream of the file content.
+- **Response**: JSON containing the created attachment's details, including its public access `url` on success.
+
 ---
 
 ## Auth
@@ -532,6 +547,167 @@ def get_api_reference() -> str:
     return API_REFERENCE
 
 
+# --- Upload Endpoint ---
+async def upload_endpoint(request: Request) -> JSONResponse:
+    """HTTP streaming endpoint to upload file attachments to Outline.
+
+    This endpoint acts as a non-buffering gateway/proxy. It calls Outline's
+    attachments.create to register the metadata and obtain an upload URL,
+    then streams the incoming request body directly to S3.
+    """
+    # 1. Authorization validation
+    auth_header = request.headers.get("Authorization")
+    if not auth_header or auth_header != f"Bearer {OUTLINE_API_TOKEN}":
+        return JSONResponse(
+            {"ok": False, "error": "Unauthorized"},
+            status_code=401,
+        )
+
+    document_id = request.query_params.get("documentId")
+    if not document_id:
+        return JSONResponse(
+            {"ok": False, "error": "Missing 'documentId' query parameter"},
+            status_code=400,
+        )
+
+    filename = request.query_params.get("name")
+    if not filename:
+        return JSONResponse(
+            {"ok": False, "error": "Missing 'name' query parameter"},
+            status_code=400,
+        )
+
+    # Size is required by attachments.create
+    content_length_str = request.headers.get("content-length")
+    if not content_length_str:
+        return JSONResponse(
+            {"ok": False, "error": "Missing 'Content-Length' header"},
+            status_code=400,
+        )
+
+    try:
+        size = int(content_length_str)
+    except ValueError:
+        return JSONResponse(
+            {"ok": False, "error": "Invalid 'Content-Length' header"},
+            status_code=400,
+        )
+
+    # Validate file size limits (abuses and negative boundary checks)
+    MAX_UPLOAD_SIZE = int(os.getenv("MAX_UPLOAD_SIZE", "104857600"))  # Default 100MB
+    if size < 0:
+        return JSONResponse(
+            {"ok": False, "error": "Invalid file size (must be non-negative)"},
+            status_code=400,
+        )
+    if size > MAX_UPLOAD_SIZE:
+        return JSONResponse(
+            {"ok": False, "error": f"File too large (exceeds limit of {MAX_UPLOAD_SIZE} bytes)"},
+            status_code=413,
+        )
+
+    # Detect content type
+    content_type = (
+        request.headers.get("content-type")
+        or mimetypes.guess_type(filename)[0]
+        or "application/octet-stream"
+    )
+
+    # 2. Initialize upload session in Outline
+    create_params = {
+        "name": filename,
+        "documentId": document_id,
+        "size": size,
+        "contentType": content_type,
+    }
+
+    logger.info(f"Initiating attachment creation in Outline: {create_params}")
+    create_response = await outline_client.call("attachments.create", create_params)
+
+    if not create_response.get("ok"):
+        return JSONResponse(
+            {
+                "ok": False,
+                "error": f"Failed to initialize attachment in Outline: {create_response.get('error')}",
+            },
+            status_code=502,
+        )
+
+    attachment_data = create_response.get("data", {})
+    upload_url = attachment_data.get("uploadUrl")
+    if not upload_url:
+        return JSONResponse(
+            {"ok": False, "error": "Outline API did not return an uploadUrl"},
+            status_code=502,
+        )
+
+    # 3. Stream the request body directly to S3 upload_url
+    try:
+        # Pre-signed S3 PUT URLs usually enforce exact headers
+        headers = {
+            "Content-Type": content_type,
+            "Content-Length": str(size),
+        }
+
+        logger.info(f"Streaming file content to storage (size={size} bytes)")
+        async with httpx.AsyncClient() as client:
+            put_response = await client.put(
+                upload_url,
+                content=request.stream(),
+                headers=headers,
+                timeout=600.0,
+            )
+            put_response.raise_for_status()
+
+        logger.info("Upload to storage completed successfully")
+
+        # 4. Return success and attachment metadata
+        return JSONResponse(
+            {
+                "ok": True,
+                "data": {
+                    "id": attachment_data.get("id"),
+                    "name": attachment_data.get("name"),
+                    "size": attachment_data.get("size"),
+                    "contentType": attachment_data.get("contentType"),
+                    "url": attachment_data.get("url"),
+                },
+            }
+        )
+
+    except Exception as e:
+        # Clean up orphaned attachment record in Outline to maintain consistency
+        attachment_id = attachment_data.get("id")
+        if attachment_id:
+            logger.warning(
+                f"Cleaning up orphaned attachment {attachment_id} in Outline due to S3 upload failure"
+            )
+            try:
+                await outline_client.call("attachments.delete", {"id": attachment_id})
+            except Exception as cleanup_err:
+                logger.error(
+                    f"Failed to delete orphaned attachment {attachment_id}: {str(cleanup_err)}"
+                )
+
+        if isinstance(e, httpx.HTTPStatusError):
+            logger.error(
+                f"Storage upload HTTP error: {e.response.status_code} - {e.response.text}"
+            )
+            return JSONResponse(
+                {
+                    "ok": False,
+                    "error": f"Failed to upload attachment to storage: {str(e)}",
+                },
+                status_code=502,
+            )
+        else:
+            logger.error(f"Exception during attachment upload: {str(e)}")
+            return JSONResponse(
+                {"ok": False, "error": f"Upload stream failed: {str(e)}"},
+                status_code=500,
+            )
+
+
 # --- Health Check Endpoint ---
 async def health(request):
     """Health check endpoint for Docker/load balancer.
@@ -554,16 +730,30 @@ async def health(request):
 
 
 # --- ASGI Application ---
+@contextlib.asynccontextmanager
+async def lifespan(app: Starlette):
+    """Custom ASGI lifespan manager that integrates with FastMCP's lifespan
+    and ensures the Outline HTTP client's connections are gracefully closed
+    on server shutdown.
+    """
+    mcp_app = mcp.http_app()
+    async with mcp_app.lifespan(app):
+        yield
+        logger.info("Closing Outline client connections on server shutdown")
+        await outline_client.close()
+
+
 def create_app():
     """Create the ASGI application with health check and MCP routes."""
     mcp_app = mcp.http_app()
 
     routes = [
         Route("/health", health, methods=["GET"]),
+        Route("/upload", upload_endpoint, methods=["POST"]),
         Mount("/", app=mcp_app),
     ]
 
-    return Starlette(routes=routes, lifespan=mcp_app.lifespan)
+    return Starlette(routes=routes, lifespan=lifespan)
 
 
 # Create the app instance for uvicorn
diff --git a/test_upload.py b/test_upload.py
new file mode 100644
index 0000000..286f139
--- /dev/null
+++ b/test_upload.py
@@ -0,0 +1,259 @@
+import json
+from unittest.mock import AsyncMock, patch
+import pytest
+import httpx
+from starlette.testclient import TestClient
+from server import create_app, outline_client, OUTLINE_API_TOKEN
+
+# Helper mock responses
+MOCK_ATTACH_CREATE_SUCCESS = {
+    "ok": True,
+    "data": {
+        "id": "attachment-5678-uuid",
+        "name": "test_stream.txt",
+        "size": 34,
+        "contentType": "text/plain",
+        "uploadUrl": "https://s3.example.com/fake-bucket/test_stream.txt?signature=xyz",
+        "url": "https://docs.example.com/attachments/attachment-5678-uuid"
+    }
+}
+
+MOCK_ATTACH_CREATE_ERROR = {
+    "ok": False,
+    "error": "Document not found"
+}
+
+
+@pytest.mark.asyncio
+async def test_upload_endpoint_success():
+    """Verify that a successful stream upload coordinates with Outline,
+    streams content to S3, and returns the expected metadata.
+    """
+    file_content = b"Hello, Outline Wiki Stream upload!"
+    content_length = len(file_content)
+    document_id = "doc-1234-uuid"
+    filename = "test_stream.txt"
+    content_type = "text/plain"
+
+    app = create_app()
+
+    # Mock OutlineClient attachments.create
+    with patch.object(outline_client, "call", new_callable=AsyncMock) as mock_call:
+        mock_call.return_value = MOCK_ATTACH_CREATE_SUCCESS
+
+        # Mock S3 PUT response
+        mock_put_response = httpx.Response(
+            200, request=httpx.Request("PUT", "https://s3.example.com")
+        )
+
+        # Mock httpx.AsyncClient to intercept put
+        with patch("httpx.AsyncClient") as MockClient:
+            mock_instance = AsyncMock()
+            mock_instance.put.return_value = mock_put_response
+            MockClient.return_value.__aenter__.return_value = mock_instance
+
+            client = TestClient(app)
+            response = client.post(
+                f"/upload?documentId={document_id}&name={filename}",
+                content=file_content,
+                headers={
+                    "Content-Length": str(content_length),
+                    "Content-Type": content_type,
+                    "Authorization": f"Bearer {OUTLINE_API_TOKEN}"
+                }
+            )
+
+            assert response.status_code == 200
+            response_json = response.json()
+            assert response_json["ok"] is True
+            assert response_json["data"]["id"] == "attachment-5678-uuid"
+
+            # Verify attachments.create parameters
+            mock_call.assert_called_once_with(
+                "attachments.create",
+                {
+                    "name": filename,
+                    "documentId": document_id,
+                    "size": content_length,
+                    "contentType": content_type
+                }
+            )
+
+            # Verify S3 PUT parameters
+            mock_instance.put.assert_called_once()
+            args, kwargs = mock_instance.put.call_args
+            assert args[0] == "https://s3.example.com/fake-bucket/test_stream.txt?signature=xyz"
+            assert kwargs["headers"]["Content-Type"] == content_type
+            assert kwargs["headers"]["Content-Length"] == str(content_length)
+
+
+@pytest.mark.asyncio
+async def test_upload_endpoint_unauthorized():
+    """Verify that request with incorrect or missing auth is rejected with 401."""
+    app = create_app()
+    client = TestClient(app)
+
+    # Missing Authorization header
+    response = client.post(
+        "/upload?documentId=doc-123&name=test.txt",
+        content=b"content",
+        headers={"Content-Length": "7"}
+    )
+    assert response.status_code == 401
+    assert response.json()["error"] == "Unauthorized"
+
+    # Incorrect Authorization token
+    response = client.post(
+        "/upload?documentId=doc-123&name=test.txt",
+        content=b"content",
+        headers={
+            "Content-Length": "7",
+            "Authorization": "Bearer wrong-token"
+        }
+    )
+    assert response.status_code == 401
+    assert response.json()["error"] == "Unauthorized"
+
+
+@pytest.mark.asyncio
+async def test_upload_endpoint_oversized_file():
+    """Verify that oversized files are rejected with 413 Payload Too Large."""
+    app = create_app()
+    client = TestClient(app)
+
+    # Content length greater than default MAX_UPLOAD_SIZE (100MB)
+    oversized_length = 104857600 + 1 # 100MB + 1 byte
+    response = client.post(
+        "/upload?documentId=doc-123&name=test.txt",
+        headers={
+            "Content-Length": str(oversized_length),
+            "Authorization": f"Bearer {OUTLINE_API_TOKEN}"
+        }
+    )
+    assert response.status_code == 413
+    assert "File too large" in response.json()["error"]
+
+
+@pytest.mark.asyncio
+async def test_upload_endpoint_negative_size():
+    """Verify that negative file size content lengths are rejected with 400."""
+    app = create_app()
+    client = TestClient(app)
+
+    response = client.post(
+        "/upload?documentId=doc-123&name=test.txt",
+        headers={
+            "Content-Length": "-10",
+            "Authorization": f"Bearer {OUTLINE_API_TOKEN}"
+        }
+    )
+    assert response.status_code == 400
+    assert "Invalid file size" in response.json()["error"]
+
+
+@pytest.mark.asyncio
+async def test_upload_endpoint_missing_params():
+    """Verify missing query params are handled with 400."""
+    app = create_app()
+    client = TestClient(app)
+
+    # Missing documentId
+    response = client.post(
+        "/upload?name=test.txt",
+        content=b"content",
+        headers={
+            "Content-Length": "7",
+            "Authorization": f"Bearer {OUTLINE_API_TOKEN}"
+        }
+    )
+    assert response.status_code == 400
+    assert "documentId" in response.json()["error"]
+
+    # Missing name
+    response = client.post(
+        "/upload?documentId=doc-123",
+        content=b"content",
+        headers={
+            "Content-Length": "7",
+            "Authorization": f"Bearer {OUTLINE_API_TOKEN}"
+        }
+    )
+    assert response.status_code == 400
+    assert "name" in response.json()["error"]
+
+
+@pytest.mark.asyncio
+async def test_upload_endpoint_missing_content_length():
+    """Verify that missing Content-Length header is handled correctly."""
+    app = create_app()
+    client = TestClient(app)
+
+    # We send a generator to prevent TestClient from auto-populating Content-Length
+    def dummy_generator():
+        yield b"chunk"
+
+    response = client.post(
+        "/upload?documentId=doc-123&name=test.txt",
+        content=dummy_generator(),
+        headers={"Authorization": f"Bearer {OUTLINE_API_TOKEN}"}
+    )
+    assert response.status_code == 400
+    assert "Content-Length" in response.json()["error"]
+
+
+@pytest.mark.asyncio
+async def test_upload_endpoint_outline_create_failure():
+    """Verify that Outline registration failures are handled correctly."""
+    app = create_app()
+
+    with patch.object(outline_client, "call", new_callable=AsyncMock) as mock_call:
+        mock_call.return_value = MOCK_ATTACH_CREATE_ERROR
+
+        client = TestClient(app)
+        response = client.post(
+            "/upload?documentId=doc-123&name=test.txt",
+            content=b"content",
+            headers={
+                "Content-Length": "7",
+                "Authorization": f"Bearer {OUTLINE_API_TOKEN}"
+            }
+        )
+
+        assert response.status_code == 502
+        assert "Failed to initialize attachment" in response.json()["error"]
+
+
+@pytest.mark.asyncio
+async def test_upload_endpoint_s3_failure_cleanup():
+    """Verify that if the S3 upload fails, attachments.delete is called on Outline to clean up."""
+    app = create_app()
+
+    with patch.object(outline_client, "call", new_callable=AsyncMock) as mock_call:
+        mock_call.return_value = MOCK_ATTACH_CREATE_SUCCESS
+
+        # S3 PUT failure response
+        mock_put_response = httpx.Response(
+            500, request=httpx.Request("PUT", "https://s3.example.com")
+        )
+
+        with patch("httpx.AsyncClient") as MockClient:
+            mock_instance = AsyncMock()
+            mock_instance.put.return_value = mock_put_response
+            MockClient.return_value.__aenter__.return_value = mock_instance
+
+            client = TestClient(app)
+            response = client.post(
+                "/upload?documentId=doc-123&name=test.txt",
+                content=b"content",
+                headers={
+                    "Content-Length": "7",
+                    "Authorization": f"Bearer {OUTLINE_API_TOKEN}"
+                }
+            )
+
+            # S3 returns 500 so our gateway should return 502
+            assert response.status_code == 502
+            assert "Failed to upload attachment to storage" in response.json()["error"]
+
+            # Verify that attachments.delete was called to rollback the creation
+            mock_call.assert_any_call("attachments.delete", {"id": "attachment-5678-uuid"})