Everyone assumes that moving files between your Mac and a remote Windows session should be simple. It isn't. Or rather, it can be, but only if your environment is configured for it.

If you're using Parallels Client to connect to Remote Desktop Services, you've probably hit this wall. You have a file on your Mac. You need it in Windows. And nothing seems to work.

Here's what I've learned about making file transfer actually happen.

Start With Drive Redirection

This is the cleanest approach when it's available. Drive redirection lets your Mac folders appear inside the Windows session as mapped network drives. Your Documents folder becomes \tsclient\Documents. Your Desktop becomes \tsclient\Desktop. Drag and drop works. It feels native.

To enable it, open Parallels Client, right-click your connection, go to Connection Properties, then Local Resources. Turn on Disk Drives. Reconnect.

If it works, you're done. If it doesn't, keep reading.

Try Copy and Paste

Many Parallels Client setups allow clipboard sharing for files, text, and images. Copy a file on your Mac with Command-C, paste inside Windows with Ctrl-V.

When it works, it's convenient. When it doesn't, there's no error message. It just fails silently. That usually means the server policy has it blocked.

Set Up an SMB Share

If drive redirection is disabled by your admin, you can still transfer files through a shared network folder. This requires that both machines are on the same network and that you control your Mac's sharing settings.

On your Mac, enable File Sharing in System Settings under General, then Sharing. Share a folder. Note your Mac's local IP address.

On the Windows side, open File Explorer and navigate to your Mac's IP, like \192.168.1.45. Enter your Mac credentials. Your shared folder appears.

This approach works reliably if you have the network access. It doesn't depend on RDS policies.

Use Cloud Storage

If the remote server has internet access, cloud storage becomes your fallback. OneDrive, Google Drive, Dropbox, SharePoint, iCloud. Upload on one side, download on the other.

This bypasses drive redirection restrictions entirely. It's not elegant, but it works even in locked-down environments.

When Nothing Works

Some RDS admins disable all file transfer options deliberately. They're preventing data exfiltration. They're blocking malware from home machines. They're maintaining compliance with HIPAA or SOC2.

If you've tried everything and nothing works, it's probably intentional. In those cases, email attachments or a company-approved secure upload system might be your only option.

The Real Lesson

File transfer with Parallels Client isn't a technical problem. It's a policy problem. The tools exist. The question is whether your environment allows them.

Before spending a lot of time troubleshooting, ask your admin what's enabled. Start with drive redirection. Fall back to SMB or cloud storage. Accept that some environments are locked down for good reasons.