diff --git a/docs/cloud-cli.md b/docs/cloud-cli.md
index 0b0534b02..2bfdc9f0c 100644
--- a/docs/cloud-cli.md
+++ b/docs/cloud-cli.md
@@ -7,6 +7,7 @@ The Basic Memory Cloud CLI provides seamless integration between local and cloud
 The cloud CLI enables you to:
 - **Toggle cloud mode** with `bm cloud login` / `bm cloud logout`
 - **Use regular commands in cloud mode**: `bm project`, `bm sync`, `bm tool` all work with cloud
+- **Upload local files** directly to cloud projects via `bm cloud upload`
 - **Bidirectional sync** with rclone bisync (recommended for most users)
 - **Direct file access** via rclone mount (alternative workflow)
 - **Integrity verification** with `bm cloud check`
@@ -160,6 +161,69 @@ bm project list
 
 This Dropbox-like workflow means you don't need to manually coordinate projects between local and cloud.
 
+### Uploading Local Files
+
+You can directly upload local files or directories to cloud projects using `bm cloud upload`. This is useful for:
+- Migrating existing local projects to the cloud
+- Quickly uploading specific files or directories
+- One-time bulk uploads without setting up sync
+
+**Basic Usage:**
+
+```bash
+# Upload a directory to existing project
+bm cloud upload ~/my-notes --project research
+
+# Upload a single file
+bm cloud upload important-doc.md --project research
+```
+
+**Create Project On-the-Fly:**
+
+If the target project doesn't exist yet, use `--create-project`:
+
+```bash
+# Upload and create project in one step
+bm cloud upload ~/local-project --project new-research --create-project
+```
+
+**Skip Automatic Sync:**
+
+By default, the command syncs the project after upload to index the files. To skip this:
+
+```bash
+# Upload without triggering sync
+bm cloud upload ~/bulk-data --project archives --no-sync
+```
+
+**File Filtering:**
+
+The upload command respects `.bmignore` and `.gitignore` patterns, automatically excluding:
+- Hidden files (`.git`, `.DS_Store`)
+- Build artifacts (`node_modules`, `__pycache__`)
+- Database files (`*.db`, `*.db-wal`)
+- Environment files (`.env`)
+
+To customize what gets uploaded, edit `~/.basic-memory/.bmignore`.
+
+**Complete Example:**
+
+```bash
+# 1. Login to cloud
+bm cloud login
+
+# 2. Upload local project (creates project if needed)
+bm cloud upload ~/Documents/research-notes --project research --create-project
+
+# 3. Verify upload
+bm project list
+```
+
+**Notes:**
+- Files are uploaded directly via WebDAV (no sync setup required)
+- Uploads are immediate and don't require bisync or mount
+- Use this for migration or one-time uploads; use `bm sync` for ongoing synchronization
+
 ## File Synchronization
 
 ### The `bm sync` Command (Cloud Mode Aware)
@@ -628,6 +692,15 @@ bm cloud check                   # Full integrity check
 bm cloud check --one-way         # Faster one-way check
 ```
 
+### File Upload
+
+```bash
+# Upload files/directories to cloud projects
+bm cloud upload <path> --project <name>              # Upload to existing project
+bm cloud upload <path> -p <name> --create-project    # Upload and create project
+bm cloud upload <path> -p <name> --no-sync           # Upload without syncing
+```
+
 ### Direct File Access (Mount)
 
 ```bash
diff --git a/pyproject.toml b/pyproject.toml
index a90869808..100b298e2 100644
--- a/pyproject.toml
+++ b/pyproject.toml
@@ -34,7 +34,7 @@ dependencies = [
     "pyjwt>=2.10.1",
     "python-dotenv>=1.1.0",
     "pytest-aio>=1.9.0",
-    "aiofiles>=24.1.0",  # Async file I/O
+    "aiofiles>=24.1.0", # Async file I/O
 ]
 
 
diff --git a/src/basic_memory/cli/commands/cloud/__init__.py b/src/basic_memory/cli/commands/cloud/__init__.py
index 85b431990..1b6146e2b 100644
--- a/src/basic_memory/cli/commands/cloud/__init__.py
+++ b/src/basic_memory/cli/commands/cloud/__init__.py
@@ -2,4 +2,5 @@
 
 # Import all commands to register them with typer
 from basic_memory.cli.commands.cloud.core_commands import *  # noqa: F401,F403
-from basic_memory.cli.commands.cloud.api_client import get_authenticated_headers  # noqa: F401
+from basic_memory.cli.commands.cloud.api_client import get_authenticated_headers, get_cloud_config  # noqa: F401
+from basic_memory.cli.commands.cloud.upload_command import *  # noqa: F401,F403
diff --git a/src/basic_memory/cli/commands/cloud/bisync_commands.py b/src/basic_memory/cli/commands/cloud/bisync_commands.py
index 4fe4d26ea..25aa1a6de 100644
--- a/src/basic_memory/cli/commands/cloud/bisync_commands.py
+++ b/src/basic_memory/cli/commands/cloud/bisync_commands.py
@@ -12,6 +12,10 @@
 from rich.table import Table
 
 from basic_memory.cli.commands.cloud.api_client import CloudAPIError, make_api_request
+from basic_memory.cli.commands.cloud.cloud_utils import (
+    create_cloud_project,
+    fetch_cloud_projects,
+)
 from basic_memory.cli.commands.cloud.rclone_config import (
     add_tenant_to_rclone_config,
 )
@@ -21,11 +25,7 @@
 from basic_memory.schemas.cloud import (
     TenantMountInfo,
     MountCredentials,
-    CloudProjectList,
-    CloudProjectCreateRequest,
-    CloudProjectCreateResponse,
 )
-from basic_memory.utils import generate_permalink
 
 console = Console()
 
@@ -110,24 +110,6 @@ async def generate_mount_credentials(tenant_id: str) -> MountCredentials:
         raise BisyncError(f"Failed to generate credentials: {e}") from e
 
 
-async def fetch_cloud_projects() -> CloudProjectList:
-    """Fetch list of projects from cloud API.
-
-    Returns:
-        CloudProjectList with projects from cloud
-    """
-    try:
-        config_manager = ConfigManager()
-        config = config_manager.config
-        host_url = config.cloud_host.rstrip("/")
-
-        response = await make_api_request(method="GET", url=f"{host_url}/proxy/projects/projects")
-
-        return CloudProjectList.model_validate(response.json())
-    except Exception as e:
-        raise BisyncError(f"Failed to fetch cloud projects: {e}") from e
-
-
 def scan_local_directories(sync_dir: Path) -> list[str]:
     """Scan local sync directory for project folders.
 
@@ -148,41 +130,6 @@ def scan_local_directories(sync_dir: Path) -> list[str]:
     return directories
 
 
-async def create_cloud_project(project_name: str) -> CloudProjectCreateResponse:
-    """Create a new project on cloud.
-
-    Args:
-        project_name: Name of project to create
-
-    Returns:
-        CloudProjectCreateResponse with project details from API
-    """
-    try:
-        config_manager = ConfigManager()
-        config = config_manager.config
-        host_url = config.cloud_host.rstrip("/")
-
-        # Use generate_permalink to ensure consistent naming
-        project_path = generate_permalink(project_name)
-
-        project_data = CloudProjectCreateRequest(
-            name=project_name,
-            path=project_path,
-            set_default=False,
-        )
-
-        response = await make_api_request(
-            method="POST",
-            url=f"{host_url}/proxy/projects/projects",
-            headers={"Content-Type": "application/json"},
-            json_data=project_data.model_dump(),
-        )
-
-        return CloudProjectCreateResponse.model_validate(response.json())
-    except Exception as e:
-        raise BisyncError(f"Failed to create cloud project '{project_name}': {e}") from e
-
-
 def get_bisync_state_path(tenant_id: str) -> Path:
     """Get path to bisync state directory."""
     return Path.home() / ".basic-memory" / "bisync-state" / tenant_id
diff --git a/src/basic_memory/cli/commands/cloud/cloud_utils.py b/src/basic_memory/cli/commands/cloud/cloud_utils.py
new file mode 100644
index 000000000..294d2613f
--- /dev/null
+++ b/src/basic_memory/cli/commands/cloud/cloud_utils.py
@@ -0,0 +1,100 @@
+"""Shared utilities for cloud operations."""
+
+from basic_memory.cli.commands.cloud.api_client import make_api_request
+from basic_memory.config import ConfigManager
+from basic_memory.schemas.cloud import (
+    CloudProjectList,
+    CloudProjectCreateRequest,
+    CloudProjectCreateResponse,
+)
+from basic_memory.utils import generate_permalink
+
+
+class CloudUtilsError(Exception):
+    """Exception raised for cloud utility errors."""
+
+    pass
+
+
+async def fetch_cloud_projects() -> CloudProjectList:
+    """Fetch list of projects from cloud API.
+
+    Returns:
+        CloudProjectList with projects from cloud
+    """
+    try:
+        config_manager = ConfigManager()
+        config = config_manager.config
+        host_url = config.cloud_host.rstrip("/")
+
+        response = await make_api_request(method="GET", url=f"{host_url}/proxy/projects/projects")
+
+        return CloudProjectList.model_validate(response.json())
+    except Exception as e:
+        raise CloudUtilsError(f"Failed to fetch cloud projects: {e}") from e
+
+
+async def create_cloud_project(project_name: str) -> CloudProjectCreateResponse:
+    """Create a new project on cloud.
+
+    Args:
+        project_name: Name of project to create
+
+    Returns:
+        CloudProjectCreateResponse with project details from API
+    """
+    try:
+        config_manager = ConfigManager()
+        config = config_manager.config
+        host_url = config.cloud_host.rstrip("/")
+
+        # Use generate_permalink to ensure consistent naming
+        project_path = generate_permalink(project_name)
+
+        project_data = CloudProjectCreateRequest(
+            name=project_name,
+            path=project_path,
+            set_default=False,
+        )
+
+        response = await make_api_request(
+            method="POST",
+            url=f"{host_url}/proxy/projects/projects",
+            headers={"Content-Type": "application/json"},
+            json_data=project_data.model_dump(),
+        )
+
+        return CloudProjectCreateResponse.model_validate(response.json())
+    except Exception as e:
+        raise CloudUtilsError(f"Failed to create cloud project '{project_name}': {e}") from e
+
+
+async def sync_project(project_name: str) -> None:
+    """Trigger sync for a specific project on cloud.
+
+    Args:
+        project_name: Name of project to sync
+    """
+    try:
+        from basic_memory.cli.commands.command_utils import run_sync
+
+        await run_sync(project=project_name)
+    except Exception as e:
+        raise CloudUtilsError(f"Failed to sync project '{project_name}': {e}") from e
+
+
+async def project_exists(project_name: str) -> bool:
+    """Check if a project exists on cloud.
+
+    Args:
+        project_name: Name of project to check
+
+    Returns:
+        True if project exists, False otherwise
+    """
+    try:
+        projects = await fetch_cloud_projects()
+        project_names = {p.name for p in projects.projects}
+        return project_name in project_names
+    except Exception:
+        return False
diff --git a/src/basic_memory/cli/commands/cloud/upload.py b/src/basic_memory/cli/commands/cloud/upload.py
new file mode 100644
index 000000000..87cc6d6fa
--- /dev/null
+++ b/src/basic_memory/cli/commands/cloud/upload.py
@@ -0,0 +1,128 @@
+"""WebDAV upload functionality for basic-memory projects."""
+
+import os
+from pathlib import Path
+
+import aiofiles
+import httpx
+
+from basic_memory.ignore_utils import load_gitignore_patterns, should_ignore_path
+from basic_memory.mcp.async_client import get_client
+from basic_memory.mcp.tools.utils import call_put
+
+
+async def upload_path(local_path: Path, project_name: str) -> bool:
+    """
+    Upload a file or directory to cloud project via WebDAV.
+
+    Args:
+        local_path: Path to local file or directory
+        project_name: Name of cloud project (destination)
+
+    Returns:
+        True if upload succeeded, False otherwise
+    """
+    try:
+        # Resolve path
+        local_path = local_path.resolve()
+
+        # Check if path exists
+        if not local_path.exists():
+            print(f"Error: Path does not exist: {local_path}")
+            return False
+
+        # Get files to upload
+        if local_path.is_file():
+            files_to_upload = [(local_path, local_path.name)]
+        else:
+            files_to_upload = _get_files_to_upload(local_path)
+
+        if not files_to_upload:
+            print("No files found to upload")
+            return True
+
+        print(f"Found {len(files_to_upload)} file(s) to upload")
+
+        # Upload files using httpx
+        total_bytes = 0
+
+        async with get_client() as client:
+            for i, (file_path, relative_path) in enumerate(files_to_upload, 1):
+                # Build remote path: /webdav/{project_name}/{relative_path}
+                remote_path = f"/webdav/{project_name}/{relative_path}"
+                print(f"Uploading {relative_path} ({i}/{len(files_to_upload)})")
+
+                # Read file content asynchronously
+                async with aiofiles.open(file_path, "rb") as f:
+                    content = await f.read()
+
+                # Upload via HTTP PUT to WebDAV endpoint
+                response = await call_put(client, remote_path, content=content)
+                response.raise_for_status()
+
+                total_bytes += file_path.stat().st_size
+
+        # Format size based on magnitude
+        if total_bytes < 1024:
+            size_str = f"{total_bytes} bytes"
+        elif total_bytes < 1024 * 1024:
+            size_str = f"{total_bytes / 1024:.1f} KB"
+        else:
+            size_str = f"{total_bytes / (1024 * 1024):.1f} MB"
+
+        print(f"✓ Upload complete: {len(files_to_upload)} file(s) ({size_str})")
+        return True
+
+    except httpx.HTTPStatusError as e:
+        print(f"Upload failed: HTTP {e.response.status_code} - {e.response.text}")
+        return False
+    except Exception as e:
+        print(f"Upload failed: {e}")
+        return False
+
+
+def _get_files_to_upload(directory: Path) -> list[tuple[Path, str]]:
+    """
+    Get list of files to upload from directory.
+
+    Uses .bmignore and .gitignore patterns for filtering.
+
+    Args:
+        directory: Directory to scan
+
+    Returns:
+        List of (absolute_path, relative_path) tuples
+    """
+    files = []
+
+    # Load ignore patterns from .bmignore and .gitignore
+    ignore_patterns = load_gitignore_patterns(directory)
+
+    # Walk through directory
+    for root, dirs, filenames in os.walk(directory):
+        root_path = Path(root)
+
+        # Filter directories based on ignore patterns
+        filtered_dirs = []
+        for d in dirs:
+            dir_path = root_path / d
+            if not should_ignore_path(dir_path, directory, ignore_patterns):
+                filtered_dirs.append(d)
+        dirs[:] = filtered_dirs
+
+        # Process files
+        for filename in filenames:
+            file_path = root_path / filename
+
+            # Check if file should be ignored
+            if should_ignore_path(file_path, directory, ignore_patterns):
+                continue
+
+            # Calculate relative path for remote
+            rel_path = file_path.relative_to(directory)
+            # Use forward slashes for WebDAV paths
+            remote_path = str(rel_path).replace("\\", "/")
+
+            files.append((file_path, remote_path))
+
+    return files
diff --git a/src/basic_memory/cli/commands/cloud/upload_command.py b/src/basic_memory/cli/commands/cloud/upload_command.py
new file mode 100644
index 000000000..3de072070
--- /dev/null
+++ b/src/basic_memory/cli/commands/cloud/upload_command.py
@@ -0,0 +1,94 @@
+"""Upload CLI commands for basic-memory projects."""
+
+import asyncio
+from pathlib import Path
+
+import typer
+from rich.console import Console
+
+from basic_memory.cli.app import cloud_app
+from basic_memory.cli.commands.cloud.cloud_utils import (
+    create_cloud_project,
+    project_exists,
+    sync_project,
+)
+from basic_memory.cli.commands.cloud.upload import upload_path
+
+console = Console()
+
+
+@cloud_app.command("upload")
+def upload(
+    path: Path = typer.Argument(
+        ...,
+        help="Path to local file or directory to upload",
+        exists=True,
+        readable=True,
+        resolve_path=True,
+    ),
+    project: str = typer.Option(
+        ...,
+        "--project",
+        "-p",
+        help="Cloud project name (destination)",
+    ),
+    create_project: bool = typer.Option(
+        False,
+        "--create-project",
+        "-c",
+        help="Create project if it doesn't exist",
+    ),
+    sync: bool = typer.Option(
+        True,
+        "--sync/--no-sync",
+        help="Sync project after upload (default: true)",
+    ),
+) -> None:
+    """Upload local files or directories to cloud project via WebDAV.
+
+    Examples:
+      bm cloud upload ~/my-notes --project research
+      bm cloud upload notes.md --project research --create-project
+      bm cloud upload ~/docs --project work --no-sync
+    """
+
+    async def _upload():
+        # Check if project exists
+        if not await project_exists(project):
+            if create_project:
+                console.print(f"[blue]Creating cloud project '{project}'...[/blue]")
+                try:
+                    await create_cloud_project(project)
+                    console.print(f"[green]✓ Created project '{project}'[/green]")
+                except Exception as e:
+                    console.print(f"[red]Failed to create project: {e}[/red]")
+                    raise typer.Exit(1)
+            else:
+                console.print(
+                    f"[red]Project '{project}' does not exist.[/red]\n"
+                    f"[yellow]Options:[/yellow]\n"
+                    f"  1. Create it first: bm project add {project}\n"
+                    f"  2. Use --create-project flag to create automatically"
+                )
+                raise typer.Exit(1)
+
+        # Perform upload
+        console.print(f"[blue]Uploading {path} to project '{project}'...[/blue]")
+        success = await upload_path(path, project)
+        if not success:
+            console.print("[red]Upload failed[/red]")
+            raise typer.Exit(1)
+
+        console.print(f"[green]✅ Successfully uploaded to '{project}'[/green]")
+
+        # Sync project if requested
+        if sync:
+            console.print(f"[blue]Syncing project '{project}'...[/blue]")
+            try:
+                await sync_project(project)
+                console.print("[green]✓ Project synced[/green]")
+            except Exception as e:
+                console.print(f"[yellow]Warning: Sync failed: {e}[/yellow]")
+                console.print("[dim]Files uploaded but may not be indexed yet[/dim]")
+
+    asyncio.run(_upload())
diff --git a/src/basic_memory/mcp/async_client.py b/src/basic_memory/mcp/async_client.py
index 77b7f48a3..499fca689 100644
--- a/src/basic_memory/mcp/async_client.py
+++ b/src/basic_memory/mcp/async_client.py
@@ -87,6 +87,7 @@ async def get_client() -> AsyncIterator[AsyncClient]:
             # Auth header set ONCE at client creation
             proxy_base_url = f"{config.cloud_host}/proxy"
             logger.info(f"Creating HTTP client for cloud proxy at: {proxy_base_url}")
+            print(f"proxy_base_url:  {proxy_base_url}")
             async with AsyncClient(
                 base_url=proxy_base_url,
                 headers={"Authorization": f"Bearer {token}"},
diff --git a/tests/cli/test_bisync_commands.py b/tests/cli/test_bisync_commands.py
index 30c5354ae..7334bd891 100644
--- a/tests/cli/test_bisync_commands.py
+++ b/tests/cli/test_bisync_commands.py
@@ -404,11 +404,9 @@ class TestCloudProjectAutoRegistration:
     @pytest.mark.asyncio
     async def test_extracts_directory_names_from_cloud_paths(self):
         """Test extraction of directory names from cloud project paths."""
-        from basic_memory.cli.commands.cloud.bisync_commands import fetch_cloud_projects
+        from basic_memory.cli.commands.cloud.cloud_utils import fetch_cloud_projects
 
-        with patch(
-            "basic_memory.cli.commands.cloud.bisync_commands.make_api_request"
-        ) as mock_request:
+        with patch("basic_memory.cli.commands.cloud.cloud_utils.make_api_request") as mock_request:
             mock_response = Mock()
             mock_response.json.return_value = {
                 "projects": [
@@ -435,13 +433,11 @@ async def test_extracts_directory_names_from_cloud_paths(self):
     @pytest.mark.asyncio
     async def test_create_cloud_project_generates_permalink(self):
         """Test that create_cloud_project generates correct permalink."""
-        from basic_memory.cli.commands.cloud.bisync_commands import create_cloud_project
+        from basic_memory.cli.commands.cloud.cloud_utils import create_cloud_project
 
-        with patch(
-            "basic_memory.cli.commands.cloud.bisync_commands.make_api_request"
-        ) as mock_request:
+        with patch("basic_memory.cli.commands.cloud.cloud_utils.make_api_request") as mock_request:
             with patch(
-                "basic_memory.cli.commands.cloud.bisync_commands.generate_permalink"
+                "basic_memory.cli.commands.cloud.cloud_utils.generate_permalink"
             ) as mock_permalink:
                 mock_permalink.return_value = "my-new-project"
                 mock_response = Mock()
diff --git a/tests/cli/test_cloud_utils.py b/tests/cli/test_cloud_utils.py
new file mode 100644
index 000000000..3acef7298
--- /dev/null
+++ b/tests/cli/test_cloud_utils.py
@@ -0,0 +1,316 @@
+"""Tests for cloud_utils module."""
+
+from unittest.mock import AsyncMock, Mock, patch
+
+import pytest
+
+from basic_memory.cli.commands.cloud.cloud_utils import (
+    CloudUtilsError,
+    create_cloud_project,
+    fetch_cloud_projects,
+    project_exists,
+    sync_project,
+)
+
+
+class TestFetchCloudProjects:
+    """Tests for fetch_cloud_projects()."""
+
+    @pytest.mark.asyncio
+    async def test_fetches_projects_successfully(self):
+        """Test successful fetch of cloud projects."""
+        with patch("basic_memory.cli.commands.cloud.cloud_utils.make_api_request") as mock_request:
+            with patch("basic_memory.cli.commands.cloud.cloud_utils.ConfigManager") as mock_config:
+                # Setup config
+                mock_config.return_value.config.cloud_host = "https://example.com"
+
+                # Mock API response
+                mock_response = Mock()
+                mock_response.json.return_value = {
+                    "projects": [
+                        {"name": "Project 1", "path": "/app/data/project-1"},
+                        {"name": "Project 2", "path": "/app/data/project-2"},
+                    ]
+                }
+                mock_request.return_value = mock_response
+
+                result = await fetch_cloud_projects()
+
+        # Verify result
+        assert len(result.projects) == 2
+        assert result.projects[0].name == "Project 1"
+        assert result.projects[1].name == "Project 2"
+
+        # Verify API was called correctly
+        mock_request.assert_called_once_with(
+            method="GET", url="https://example.com/proxy/projects/projects"
+        )
+
+    @pytest.mark.asyncio
+    async def test_strips_trailing_slash_from_host(self):
+        """Test that trailing slash is stripped from cloud_host."""
+        with patch("basic_memory.cli.commands.cloud.cloud_utils.make_api_request") as mock_request:
+            with patch("basic_memory.cli.commands.cloud.cloud_utils.ConfigManager") as mock_config:
+                # Setup config with trailing slash
+                mock_config.return_value.config.cloud_host = "https://example.com/"
+
+                mock_response = Mock()
+                mock_response.json.return_value = {"projects": []}
+                mock_request.return_value = mock_response
+
+                await fetch_cloud_projects()
+
+        # Verify trailing slash was removed
+        call_args = mock_request.call_args
+        assert call_args[1]["url"] == "https://example.com/proxy/projects/projects"
+
+    @pytest.mark.asyncio
+    async def test_raises_error_on_api_failure(self):
+        """Test that CloudUtilsError is raised on API failure."""
+        with patch("basic_memory.cli.commands.cloud.cloud_utils.make_api_request") as mock_request:
+            with patch("basic_memory.cli.commands.cloud.cloud_utils.ConfigManager") as mock_config:
+                mock_config.return_value.config.cloud_host = "https://example.com"
+                mock_request.side_effect = Exception("API Error")
+
+                with pytest.raises(CloudUtilsError) as exc_info:
+                    await fetch_cloud_projects()
+
+        assert "Failed to fetch cloud projects" in str(exc_info.value)
+
+    @pytest.mark.asyncio
+    async def test_handles_empty_project_list(self):
+        """Test handling of empty project list."""
+        with patch("basic_memory.cli.commands.cloud.cloud_utils.make_api_request") as mock_request:
+            with patch("basic_memory.cli.commands.cloud.cloud_utils.ConfigManager") as mock_config:
+                mock_config.return_value.config.cloud_host = "https://example.com"
+
+                mock_response = Mock()
+                mock_response.json.return_value = {"projects": []}
+                mock_request.return_value = mock_response
+
+                result = await fetch_cloud_projects()
+
+        assert len(result.projects) == 0
+
+
+class TestCreateCloudProject:
+    """Tests for create_cloud_project()."""
+
+    @pytest.mark.asyncio
+    async def test_creates_project_successfully(self):
+        """Test successful project creation."""
+        with patch("basic_memory.cli.commands.cloud.cloud_utils.make_api_request") as mock_request:
+            with patch("basic_memory.cli.commands.cloud.cloud_utils.ConfigManager") as mock_config:
+                with patch(
+                    "basic_memory.cli.commands.cloud.cloud_utils.generate_permalink"
+                ) as mock_permalink:
+                    # Setup mocks
+                    mock_config.return_value.config.cloud_host = "https://example.com"
+                    mock_permalink.return_value = "my-project"
+
+                    mock_response = Mock()
+                    mock_response.json.return_value = {
+                        "name": "My Project",
+                        "path": "my-project",
+                        "message": "Created successfully",
+                    }
+                    mock_request.return_value = mock_response
+
+                    result = await create_cloud_project("My Project")
+
+        # Verify result
+        assert result.name == "My Project"
+        assert result.path == "my-project"
+        assert result.message == "Created successfully"
+
+        # Verify permalink was generated
+        mock_permalink.assert_called_once_with("My Project")
+
+        # Verify API request
+        call_args = mock_request.call_args
+        assert call_args[1]["method"] == "POST"
+        assert call_args[1]["url"] == "https://example.com/proxy/projects/projects"
+        assert call_args[1]["headers"]["Content-Type"] == "application/json"
+
+        json_data = call_args[1]["json_data"]
+        assert json_data["name"] == "My Project"
+        assert json_data["path"] == "my-project"
+        assert json_data["set_default"] is False
+
+    @pytest.mark.asyncio
+    async def test_generates_permalink_from_name(self):
+        """Test that permalink is generated from project name."""
+        with patch("basic_memory.cli.commands.cloud.cloud_utils.make_api_request") as mock_request:
+            with patch("basic_memory.cli.commands.cloud.cloud_utils.ConfigManager") as mock_config:
+                with patch(
+                    "basic_memory.cli.commands.cloud.cloud_utils.generate_permalink"
+                ) as mock_permalink:
+                    mock_config.return_value.config.cloud_host = "https://example.com"
+                    mock_permalink.return_value = "test-project-123"
+
+                    mock_response = Mock()
+                    mock_response.json.return_value = {
+                        "name": "Test Project 123",
+                        "path": "test-project-123",
+                        "message": "Created",
+                    }
+                    mock_request.return_value = mock_response
+
+                    await create_cloud_project("Test Project 123")
+
+        # Verify generate_permalink was called with project name
+        mock_permalink.assert_called_once_with("Test Project 123")
+
+    @pytest.mark.asyncio
+    async def test_raises_error_on_api_failure(self):
+        """Test that CloudUtilsError is raised on API failure."""
+        with patch("basic_memory.cli.commands.cloud.cloud_utils.make_api_request") as mock_request:
+            with patch("basic_memory.cli.commands.cloud.cloud_utils.ConfigManager") as mock_config:
+                with patch(
+                    "basic_memory.cli.commands.cloud.cloud_utils.generate_permalink"
+                ) as mock_permalink:
+                    mock_config.return_value.config.cloud_host = "https://example.com"
+                    mock_permalink.return_value = "project"
+                    mock_request.side_effect = Exception("API Error")
+
+                    with pytest.raises(CloudUtilsError) as exc_info:
+                        await create_cloud_project("Test Project")
+
+        assert "Failed to create cloud project 'Test Project'" in str(exc_info.value)
+
+    @pytest.mark.asyncio
+    async def test_strips_trailing_slash_from_host(self):
+        """Test that trailing slash is stripped from cloud_host."""
+        with patch("basic_memory.cli.commands.cloud.cloud_utils.make_api_request") as mock_request:
+            with patch("basic_memory.cli.commands.cloud.cloud_utils.ConfigManager") as mock_config:
+                with patch(
+                    "basic_memory.cli.commands.cloud.cloud_utils.generate_permalink"
+                ) as mock_permalink:
+                    mock_config.return_value.config.cloud_host = "https://example.com/"
+                    mock_permalink.return_value = "project"
+
+                    mock_response = Mock()
+                    mock_response.json.return_value = {
+                        "name": "Project",
+                        "path": "project",
+                        "message": "Created",
+                    }
+                    mock_request.return_value = mock_response
+
+                    await create_cloud_project("Project")
+
+        # Verify trailing slash was removed
+        call_args = mock_request.call_args
+        assert call_args[1]["url"] == "https://example.com/proxy/projects/projects"
+
+
+class TestSyncProject:
+    """Tests for sync_project()."""
+
+    @pytest.mark.asyncio
+    async def test_syncs_project_successfully(self):
+        """Test successful project sync."""
+        # Patch at the point where it's imported (inside the function)
+        with patch("basic_memory.cli.commands.command_utils.run_sync", new_callable=AsyncMock) as mock_sync:
+            await sync_project("test-project")
+
+        # Verify run_sync was called with project name
+        mock_sync.assert_called_once_with(project="test-project")
+
+    @pytest.mark.asyncio
+    async def test_raises_error_on_sync_failure(self):
+        """Test that CloudUtilsError is raised on sync failure."""
+        # Patch at the point where it's imported (inside the function)
+        with patch("basic_memory.cli.commands.command_utils.run_sync", new_callable=AsyncMock) as mock_sync:
+            mock_sync.side_effect = Exception("Sync failed")
+
+            with pytest.raises(CloudUtilsError) as exc_info:
+                await sync_project("test-project")
+
+        assert "Failed to sync project 'test-project'" in str(exc_info.value)
+
+
+class TestProjectExists:
+    """Tests for project_exists()."""
+
+    @pytest.mark.asyncio
+    async def test_returns_true_when_project_exists(self):
+        """Test that True is returned when project exists."""
+        from basic_memory.schemas.cloud import CloudProject, CloudProjectList
+
+        with patch(
+            "basic_memory.cli.commands.cloud.cloud_utils.fetch_cloud_projects"
+        ) as mock_fetch:
+            # Create actual CloudProject objects
+            projects = CloudProjectList(
+                projects=[
+                    CloudProject(name="project-1", path="/app/data/project-1"),
+                    CloudProject(name="test-project", path="/app/data/test-project"),
+                    CloudProject(name="project-2", path="/app/data/project-2"),
+                ]
+            )
+            mock_fetch.return_value = projects
+
+            result = await project_exists("test-project")
+
+        assert result is True
+
+    @pytest.mark.asyncio
+    async def test_returns_false_when_project_not_found(self):
+        """Test that False is returned when project doesn't exist."""
+        with patch(
+            "basic_memory.cli.commands.cloud.cloud_utils.fetch_cloud_projects"
+        ) as mock_fetch:
+            # Mock project list without matching project
+            mock_projects = Mock()
+            mock_projects.projects = [
+                Mock(name="project-1"),
+                Mock(name="project-2"),
+            ]
+            mock_fetch.return_value = mock_projects
+
+            result = await project_exists("nonexistent-project")
+
+        assert result is False
+
+    @pytest.mark.asyncio
+    async def test_returns_false_on_api_error(self):
+        """Test that False is returned on API error."""
+        with patch(
+            "basic_memory.cli.commands.cloud.cloud_utils.fetch_cloud_projects"
+        ) as mock_fetch:
+            mock_fetch.side_effect = Exception("API Error")
+
+            result = await project_exists("test-project")
+
+        # Should return False instead of raising exception
+        assert result is False
+
+    @pytest.mark.asyncio
+    async def test_handles_empty_project_list(self):
+        """Test handling of empty project list."""
+        with patch(
+            "basic_memory.cli.commands.cloud.cloud_utils.fetch_cloud_projects"
+        ) as mock_fetch:
+            mock_projects = Mock()
+            mock_projects.projects = []
+            mock_fetch.return_value = mock_projects
+
+            result = await project_exists("any-project")
+
+        assert result is False
+
+    @pytest.mark.asyncio
+    async def test_case_sensitive_matching(self):
+        """Test that project name matching is case-sensitive."""
+        with patch(
+            "basic_memory.cli.commands.cloud.cloud_utils.fetch_cloud_projects"
+        ) as mock_fetch:
+            mock_projects = Mock()
+            mock_projects.projects = [Mock(name="Test-Project")]
+            mock_fetch.return_value = mock_projects
+
+            # Different case should not match
+            result = await project_exists("test-project")
+
+        assert result is False
diff --git a/tests/cli/test_upload.py b/tests/cli/test_upload.py
new file mode 100644
index 000000000..3ed894ad4
--- /dev/null
+++ b/tests/cli/test_upload.py
@@ -0,0 +1,326 @@
+"""Tests for upload module."""
+
+import os
+from pathlib import Path
+from unittest.mock import AsyncMock, Mock, patch
+
+import httpx
+import pytest
+
+from basic_memory.cli.commands.cloud.upload import _get_files_to_upload, upload_path
+
+
+class TestGetFilesToUpload:
+    """Tests for _get_files_to_upload()."""
+
+    def test_collects_files_from_directory(self, tmp_path):
+        """Test collecting files from a directory."""
+        # Create test directory structure
+        (tmp_path / "file1.txt").write_text("content1")
+        (tmp_path / "file2.md").write_text("content2")
+        (tmp_path / "subdir").mkdir()
+        (tmp_path / "subdir" / "file3.py").write_text("content3")
+
+        # Call with real ignore utils (no mocking)
+        result = _get_files_to_upload(tmp_path)
+
+        # Should find all 3 files
+        assert len(result) == 3
+
+        # Extract just the relative paths for easier assertion
+        relative_paths = [rel_path for _, rel_path in result]
+        assert "file1.txt" in relative_paths
+        assert "file2.md" in relative_paths
+        assert "subdir/file3.py" in relative_paths
+
+    def test_respects_gitignore_patterns(self, tmp_path):
+        """Test that gitignore patterns are respected."""
+        # Create test files
+        (tmp_path / "keep.txt").write_text("keep")
+        (tmp_path / "ignore.pyc").write_text("ignore")
+
+        # Create .gitignore file
+        gitignore_file = tmp_path / ".gitignore"
+        gitignore_file.write_text("*.pyc\n")
+
+        result = _get_files_to_upload(tmp_path)
+
+        # Should only find keep.txt (not .pyc or .gitignore itself)
+        relative_paths = [rel_path for _, rel_path in result]
+        assert "keep.txt" in relative_paths
+        assert "ignore.pyc" not in relative_paths
+
+    def test_handles_empty_directory(self, tmp_path):
+        """Test handling of empty directory."""
+        empty_dir = tmp_path / "empty"
+        empty_dir.mkdir()
+
+        result = _get_files_to_upload(empty_dir)
+
+        assert result == []
+
+    def test_converts_windows_paths_to_forward_slashes(self, tmp_path):
+        """Test that Windows backslashes are converted to forward slashes."""
+        # Create nested structure
+        (tmp_path / "dir1").mkdir()
+        (tmp_path / "dir1" / "dir2").mkdir()
+        (tmp_path / "dir1" / "dir2" / "file.txt").write_text("content")
+
+        result = _get_files_to_upload(tmp_path)
+
+        # Remote path should use forward slashes
+        _, remote_path = result[0]
+        assert "\\" not in remote_path  # No backslashes
+        assert "dir1/dir2/file.txt" == remote_path
+
+
+class TestUploadPath:
+    """Tests for upload_path()."""
+
+    @pytest.mark.asyncio
+    async def test_uploads_single_file(self, tmp_path):
+        """Test uploading a single file."""
+        test_file = tmp_path / "test.txt"
+        test_file.write_text("test content")
+
+        # Mock the client and HTTP response
+        mock_client = AsyncMock()
+        mock_response = Mock()
+        mock_response.raise_for_status = Mock()
+
+        with patch("basic_memory.cli.commands.cloud.upload.get_client") as mock_get_client:
+            with patch("basic_memory.cli.commands.cloud.upload.call_put") as mock_put:
+                with patch("aiofiles.open", create=True) as mock_aiofiles_open:
+                    # Setup mocks
+                    mock_get_client.return_value.__aenter__.return_value = mock_client
+                    mock_get_client.return_value.__aexit__.return_value = None
+                    mock_put.return_value = mock_response
+
+                    # Mock file reading
+                    mock_file = AsyncMock()
+                    mock_file.read.return_value = b"test content"
+                    mock_aiofiles_open.return_value.__aenter__.return_value = mock_file
+
+                    result = await upload_path(test_file, "test-project")
+
+        # Verify success
+        assert result is True
+
+        # Verify PUT was called with correct path
+        mock_put.assert_called_once()
+        call_args = mock_put.call_args
+        assert call_args[0][0] == mock_client
+        assert call_args[0][1] == "/webdav/test-project/test.txt"
+        assert call_args[1]["content"] == b"test content"
+
+    @pytest.mark.asyncio
+    async def test_uploads_directory(self, tmp_path):
+        """Test uploading a directory with multiple files."""
+        # Create test files
+        (tmp_path / "file1.txt").write_text("content1")
+        (tmp_path / "file2.txt").write_text("content2")
+
+        mock_client = AsyncMock()
+        mock_response = Mock()
+        mock_response.raise_for_status = Mock()
+
+        with patch("basic_memory.cli.commands.cloud.upload.get_client") as mock_get_client:
+            with patch("basic_memory.cli.commands.cloud.upload.call_put") as mock_put:
+                with patch("basic_memory.cli.commands.cloud.upload._get_files_to_upload") as mock_get_files:
+                    with patch("aiofiles.open", create=True) as mock_aiofiles_open:
+                        # Setup mocks
+                        mock_get_client.return_value.__aenter__.return_value = mock_client
+                        mock_get_client.return_value.__aexit__.return_value = None
+                        mock_put.return_value = mock_response
+
+                        # Mock file listing
+                        mock_get_files.return_value = [
+                            (tmp_path / "file1.txt", "file1.txt"),
+                            (tmp_path / "file2.txt", "file2.txt"),
+                        ]
+
+                        # Mock file reading
+                        mock_file = AsyncMock()
+                        mock_file.read.side_effect = [b"content1", b"content2"]
+                        mock_aiofiles_open.return_value.__aenter__.return_value = mock_file
+
+                        result = await upload_path(tmp_path, "test-project")
+
+        # Verify success
+        assert result is True
+
+        # Verify PUT was called twice
+        assert mock_put.call_count == 2
+
+    @pytest.mark.asyncio
+    async def test_handles_nonexistent_path(self, tmp_path):
+        """Test handling of nonexistent path."""
+        nonexistent = tmp_path / "does-not-exist"
+
+        result = await upload_path(nonexistent, "test-project")
+
+        # Should return False
+        assert result is False
+
+    @pytest.mark.asyncio
+    async def test_handles_http_error(self, tmp_path):
+        """Test handling of HTTP errors during upload."""
+        test_file = tmp_path / "test.txt"
+        test_file.write_text("test content")
+
+        mock_client = AsyncMock()
+        mock_response = Mock()
+        mock_response.status_code = 403
+        mock_response.text = "Forbidden"
+        mock_response.raise_for_status.side_effect = httpx.HTTPStatusError(
+            "Forbidden", request=Mock(), response=mock_response
+        )
+
+        with patch("basic_memory.cli.commands.cloud.upload.get_client") as mock_get_client:
+            with patch("basic_memory.cli.commands.cloud.upload.call_put") as mock_put:
+                with patch("aiofiles.open", create=True) as mock_aiofiles_open:
+                    # Setup mocks
+                    mock_get_client.return_value.__aenter__.return_value = mock_client
+                    mock_get_client.return_value.__aexit__.return_value = None
+                    mock_put.return_value = mock_response
+
+                    # Mock file reading
+                    mock_file = AsyncMock()
+                    mock_file.read.return_value = b"test content"
+                    mock_aiofiles_open.return_value.__aenter__.return_value = mock_file
+
+                    result = await upload_path(test_file, "test-project")
+
+        # Should return False on error
+        assert result is False
+
+    @pytest.mark.asyncio
+    async def test_handles_empty_directory(self, tmp_path):
+        """Test uploading an empty directory."""
+        empty_dir = tmp_path / "empty"
+        empty_dir.mkdir()
+
+        with patch("basic_memory.cli.commands.cloud.upload._get_files_to_upload") as mock_get_files:
+            mock_get_files.return_value = []
+
+            result = await upload_path(empty_dir, "test-project")
+
+        # Should return True (no-op success)
+        assert result is True
+
+    @pytest.mark.asyncio
+    async def test_formats_file_size_bytes(self, tmp_path, capsys):
+        """Test file size formatting for small files (bytes)."""
+        test_file = tmp_path / "small.txt"
+        test_file.write_text("hi")  # 2 bytes
+
+        mock_client = AsyncMock()
+        mock_response = Mock()
+        mock_response.raise_for_status = Mock()
+
+        with patch("basic_memory.cli.commands.cloud.upload.get_client") as mock_get_client:
+            with patch("basic_memory.cli.commands.cloud.upload.call_put") as mock_put:
+                with patch("aiofiles.open", create=True) as mock_aiofiles_open:
+                    mock_get_client.return_value.__aenter__.return_value = mock_client
+                    mock_get_client.return_value.__aexit__.return_value = None
+                    mock_put.return_value = mock_response
+
+                    mock_file = AsyncMock()
+                    mock_file.read.return_value = b"hi"
+                    mock_aiofiles_open.return_value.__aenter__.return_value = mock_file
+
+                    await upload_path(test_file, "test-project")
+
+        # Check output contains "bytes"
+        captured = capsys.readouterr()
+        assert "bytes" in captured.out
+
+    @pytest.mark.asyncio
+    async def test_formats_file_size_kilobytes(self, tmp_path, capsys):
+        """Test file size formatting for medium files (KB)."""
+        test_file = tmp_path / "medium.txt"
+        # Create file with 2KB of content
+        test_file.write_text("x" * 2048)
+
+        mock_client = AsyncMock()
+        mock_response = Mock()
+        mock_response.raise_for_status = Mock()
+
+        with patch("basic_memory.cli.commands.cloud.upload.get_client") as mock_get_client:
+            with patch("basic_memory.cli.commands.cloud.upload.call_put") as mock_put:
+                with patch("aiofiles.open", create=True) as mock_aiofiles_open:
+                    mock_get_client.return_value.__aenter__.return_value = mock_client
+                    mock_get_client.return_value.__aexit__.return_value = None
+                    mock_put.return_value = mock_response
+
+                    mock_file = AsyncMock()
+                    mock_file.read.return_value = b"x" * 2048
+                    mock_aiofiles_open.return_value.__aenter__.return_value = mock_file
+
+                    await upload_path(test_file, "test-project")
+
+        # Check output contains "KB"
+        captured = capsys.readouterr()
+        assert "KB" in captured.out
+
+    @pytest.mark.asyncio
+    async def test_formats_file_size_megabytes(self, tmp_path, capsys):
+        """Test file size formatting for large files (MB)."""
+        test_file = tmp_path / "large.txt"
+        # Create file with 2MB of content
+        test_file.write_text("x" * (2 * 1024 * 1024))
+
+        mock_client = AsyncMock()
+        mock_response = Mock()
+        mock_response.raise_for_status = Mock()
+
+        with patch("basic_memory.cli.commands.cloud.upload.get_client") as mock_get_client:
+            with patch("basic_memory.cli.commands.cloud.upload.call_put") as mock_put:
+                with patch("aiofiles.open", create=True) as mock_aiofiles_open:
+                    mock_get_client.return_value.__aenter__.return_value = mock_client
+                    mock_get_client.return_value.__aexit__.return_value = None
+                    mock_put.return_value = mock_response
+
+                    mock_file = AsyncMock()
+                    mock_file.read.return_value = b"x" * (2 * 1024 * 1024)
+                    mock_aiofiles_open.return_value.__aenter__.return_value = mock_file
+
+                    await upload_path(test_file, "test-project")
+
+        # Check output contains "MB"
+        captured = capsys.readouterr()
+        assert "MB" in captured.out
+
+    @pytest.mark.asyncio
+    async def test_builds_correct_webdav_path(self, tmp_path):
+        """Test that WebDAV path is correctly constructed."""
+        # Create nested structure
+        (tmp_path / "subdir").mkdir()
+        test_file = tmp_path / "subdir" / "file.txt"
+        test_file.write_text("content")
+
+        mock_client = AsyncMock()
+        mock_response = Mock()
+        mock_response.raise_for_status = Mock()
+
+        with patch("basic_memory.cli.commands.cloud.upload.get_client") as mock_get_client:
+            with patch("basic_memory.cli.commands.cloud.upload.call_put") as mock_put:
+                with patch("basic_memory.cli.commands.cloud.upload._get_files_to_upload") as mock_get_files:
+                    with patch("aiofiles.open", create=True) as mock_aiofiles_open:
+                        mock_get_client.return_value.__aenter__.return_value = mock_client
+                        mock_get_client.return_value.__aexit__.return_value = None
+                        mock_put.return_value = mock_response
+
+                        # Mock file listing with relative path
+                        mock_get_files.return_value = [(test_file, "subdir/file.txt")]
+
+                        mock_file = AsyncMock()
+                        mock_file.read.return_value = b"content"
+                        mock_aiofiles_open.return_value.__aenter__.return_value = mock_file
+
+                        await upload_path(tmp_path, "my-project")
+
+        # Verify WebDAV path format: /webdav/{project_name}/{relative_path}
+        mock_put.assert_called_once()
+        call_args = mock_put.call_args
+        assert call_args[0][1] == "/webdav/my-project/subdir/file.txt"