Do I Allow More Than 2 RDP Sessions to a Windows Server 2016?


Remote Desktop Protocol (RDP) is a core feature for managing Windows servers. It provides remote access to server desktops, allowing administrators and authorized users to maintain systems without physical presence. However, if you're using Windows Server 2016, you may notice a limit: only two simultaneous RDP sessions are allowed by default.

So the question arises: Can you allow more than two RDP sessions on Windows Server 2016? The short answer is yes, but it depends on licensing and server roles. This article dives deep into the how and why and clearly explains the technical and legal considerations involved.

The Two RDP Session Limit: Why It Exists

By default, Windows Server 2016 allows two concurrent remote desktop sessions for administrative purposes. These sessions are not intended for regular user activity but for server management. If a third person tries to connect, they'll either receive a warning or inadvertently disconnect someone else.

This limitation exists because the standard Windows Server license does not include Remote Desktop Services (RDS) capabilities for general user access. The idea is that for anything beyond basic administration, you must properly configure the server as a Remote Desktop Session Host (RDSH) and purchase Client Access Licenses (CALs).

Why Would You Need More Than Two Sessions?

Organizations or teams often need more than two people working on a server simultaneously. Some common scenarios include:

  • Multiple administrators managing different tasks

  • Helpdesk staff assisting users or troubleshooting remotely

  • Users accessing internal tools or applications hosted on the server

  • Application developers working in a shared server environment

If these situations occur regularly, relying on only two sessions can be a bottleneck. So it’s natural to want to expand that capability.

Is It Legal to Enable More Than Two RDP Sessions?

Yes, but only with the appropriate licensing.

To go beyond two RDP sessions on Windows Server 2016, Microsoft requires you to deploy Remote Desktop Services and purchase RDS CALs. These licenses authorize additional user or device connections.

There are two types of RDS CALs:

  1. Per User CAL – Each user can connect from multiple devices.

  2. Per Device CAL – Each device can be used by multiple users.

Installing RDS and activating the proper number of CALs ensures that you remain compliant with Microsoft’s licensing agreement.

How to Enable More Than 2 RDP Sessions on Windows Server 2016

To increase RDP session limits legally and effectively, follow these steps:

Step 1: Install Remote Desktop Services

  1. Open Server Manager.

  2. Click Manage > Add Roles and Features.

  3. Select Remote Desktop Services installation.

  4. Choose Session-based desktop deployment.

  5. Install the following roles:

    • Remote Desktop Session Host (RDSH)

    • Remote Desktop Licensing

    • Optionally, Remote Desktop Connection Broker and Web Access

Step 2: Activate the License Server

  1. In Server Manager, go to Remote Desktop Services > Overview > RD Licensing.

  2. Right-click your server and choose Activate Server.

  3. Complete the wizard to register your license server with Microsoft.

Step 3: Install RDS CALs

  1. After activating the license server, open the RD Licensing Manager.

  2. Right-click the server and choose Install Licenses.

  3. Follow the wizard and enter your license key from Microsoft or your Volume Licensing partner.

Step 4: Configure Licensing Mode and License Server

To ensure that your session host uses the licensing correctly:

  1. Open Group Policy Editor (gpedit.msc).

  2. Navigate to:

    pgsql
    Computer Configuration > Administrative Templates > Windows Components > Remote Desktop Services > Remote Desktop Session Host > Licensing

  3. Set the specified remote desktop license servers.

  4. Set the Remote Desktop licensing mode to either Per User or Per Device.

Step 5: Restart the Server

Once complete, restart your server. You should now be able to support multiple RDP sessions simultaneously, depending on the number of CALs installed.

Monitoring and Managing RDP Sessions

Once your RDS setup is in place, it’s important to monitor sessions:

  • Task Manager → View connected users under the “Users” tab.

  • Use query session in Command Prompt to list active sessions.

  • Remote Desktop Services Manager or PowerShell scripts can also be used for session management.

Example PowerShell command:

powershell
Get-RDUserSession

Don’t Use Illegal Workarounds

Unofficial hacks and third-party tools are floating around that claim to allow unlimited RDP sessions by modifying system files or patching DLLs. While these might work temporarily, they carry serious risks:

  • Violation of Microsoft Licensing Terms

  • Loss of support or access to updates

  • Potential system instability

  • Security vulnerabilities

In production environments, always stick to legal, licensed configurations to ensure compliance and system integrity.

Best Practices for RDP Session Management

Even with RDS in place, good management is key:

  • Set Idle Timeouts: Disconnect or log off idle users automatically.

  • Limit Sessions per User: Prevent excessive session usage by setting quotas.

  • Audit Session Usage: Regularly review logs for unauthorized access or abnormal patterns.

  • Secure Access: Use Network Level Authentication (NLA) and multi-factor authentication (MFA).

When RDS Might Not Be the Best Fit

If your goal is just to give multiple users access to specific apps (not full desktops), consider RemoteApp deployment. It runs individual applications remotely rather than the entire desktop session.

Alternatively, for modern app hosting, some organizations are migrating to Azure Virtual Desktop (AVD) or using Windows 365, which offer cloud-hosted multi-session desktops and scalability.

Summary

FeatureWithout RDSWith RDS Role
Max RDP Sessions2Based on CALs installed
Intended UseAdmin access onlyUser access for apps/desktops
Requires RDS CALsNoYes
Licensing ComplianceLimited use onlyFully compliant
Can be monitored and managedLimitedFull session management

Final Thoughts

To wrap it up, if you need more than two RDP sessions on Windows Server 2016, the correct way to do so is by:

  1. Installing the Remote Desktop Services role

  2. Activating the license server

  3. Purchasing and applying the correct number of RDS CALs

  4. Managing and securing your environment properly

Trying to bypass this with hacks or tweaks is not only against Microsoft’s licensing agreement, but it also poses serious security and stability risks.

Always opt for the licensed route — it's scalable, secure, and reliable.

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