How to Allow Multiple Users to RDP Simultaneously on Windows Server

Windows Server ships with only 2 Remote Desktop connections, meant for administrators. To let a full team log in at once, install the Remote Desktop Session Host role. It comes with a free 120 day grace period

Plenty of IT teams need more than one person RDP’d into the same Windows Server at the same time: admins running maintenance windows, support techs helping users on the box, small teams sharing a workspace server. Out of the box, Windows Server won’t let them. Push past two logged-in users and everyone gets that “too many users signed in” popup, and the next person in the door boots someone else out to make room.

You don’t need a new server, a fresh install, or any unofficial patches to fix it. Enabling the Remote Desktop Session Host role and flipping one Group Policy setting turns the same box into a proper multi-user machine, and Microsoft’s own 120-day grace period lets you run it free while you plan the RDS User CALs. Here’s the exact walkthrough.

Before you start

• Log in as the real Administrator account, not a normal user.
• Take a snapshot or backup. We’re rebooting the server.
• OS must be Windows Server 2016, 2019 or 2022. Windows 10 or 11 can’t do multi-user RDP.

Step 1: Open PowerShell as Administrator

Right click the Start button, pick Windows PowerShell (Admin). Click Yes if Windows asks to confirm.

Right click PowerShell and pick Run as administrator.

Step 2: Install the Remote Desktop Session Host role

Paste this into PowerShell and hit Enter:

Install-WindowsFeature -Name RDS-RD-Server -IncludeManagementTools -Restart

Paste the command and press Enter.

The install runs, then the server reboots itself. Give it 3 to 5 minutes.

Installation progress climbs, then the server reboots on its own.

Step 3: Confirm the 120 day grace period

Reconnect over RDP as Administrator, open PowerShell again, run:

(Get-WmiObject -Namespace “root\cimv2\TerminalServices” -Class Win32_TerminalServiceSetting).GetGracePeriodDays()

DaysLeft 119. The clock’s running.

If DaysLeft is 0 or tiny, the grace period was already used on this server. You’ll need to buy RDS CALs before more than two users can log in.

Step 4: Open Group Policy

Press Windows + R, type gpedit.msc, hit Enter.

Type gpedit.msc to open the Local Group Policy Editor.

Step 5: Navigate to the right policy

In the left panel, walk down this path:

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

Computer Configuration, Administrative Templates, Windows Components.

Remote Desktop Services, Session Host, Connections.

Step 6: Set the session policy

In the right panel, double click “Restrict Remote Desktop Services users to a single Remote Desktop Services session”.

• If each user has their own account, pick Enabled. Recommended for 99% of setups.
• If several people share one login at the same time, pick Disabled.

Click Apply, then OK.

Enabled is the safe default.

Step 7: Push the policy live

Back in PowerShell:

gpupdate /force

One line to force the new policy live immediately.

Step 8: Test with real users

Ask two or three teammates to RDP in at the same time. Everyone should land on their desktop with no popup. To see who’s logged in:

query user /server:localhost

Troubleshooting

If it still says “too many users”, try these in order:

1. Restart the RDP service:

Get-Service TermService | Restart-Service -Force

• Find the stuck session ID with query user, then log it off:

logoff 2 /server:localhost

• Confirm the edition is Windows Server Standard or Datacenter. Essentials can’t do RDS Session Host.

Pros and cons of this approach

The upside

• One command flips the server from 2 users to unlimited during the grace period.
• 120 days is plenty of runway to test the workload and buy the right number of CALs.
• Everyone works from the same box, so software installs once and updates once.
• User profiles stay separated per person, with real audit logs on who did what.
• Cheaper than spinning up a VM per user, and easier to back up.
• Works with existing Active Directory. No rearchitecting.

The downside

• After day 120 you have to buy RDS CALs. User CALs run roughly USD 110 each at the moment.
• Shared server means one heavy user (video encode, huge Excel model) can slow everyone else down.
• Some software isn’t licensed for terminal-server use. QuickBooks Desktop and retail Office are the usual troublemakers.
• It’s a single point of failure. Server goes down, whole team stops.
• Printer redirection and specialised USB devices (dongles, scanners, POS gear) can be flaky over RDP.
• Past 10 to 15 users you have to size RAM, CPU and disk seriously. SSD isn’t optional.

Questions people actually ask

Do I really need CALs after the grace period runs out?

Yes. On day 121 the 2-user limit comes back. Microsoft ships CALs on an honour-system model, but they do audit RDS-heavy shops, and unlicensed users are the fastest way to end up with a big invoice and a compliance letter.

Can I reset the 120 days by uninstalling and reinstalling the role?

No. The grace clock is bound to the server, not to the role. Removing RDS-RD-Server and putting it back doesn’t give you a fresh 120 days. slmgr rearm doesn’t touch it either. Once the clock hits zero on that box, that’s it.

User CALs or Device CALs, which one do I want?

User CALs almost every time. One CAL per person, they can log in from any device (laptop, phone, home PC). Device CALs only make sense when several people share the same physical machine on a shift roster, like a warehouse terminal or a shop-floor kiosk.

New user gets “Access is denied”. What am I missing?

The RDS role doesn’t automatically grant login rights. Add the user to the built-in Remote Desktop Users group on the server (or add their AD group). Log off and back on and they’ll get in.

How many users can one server actually handle?

Rough rule of thumb: 1 GB of RAM per light Office or browser user, 2 GB for developers or Excel-heavy work, plus around 4 GB for the OS itself. On CPU, plan 1 vCPU for every 4 to 6 concurrent users. Disk speed matters more than people realise. On spinning disks a busy RDS server feels awful, on NVMe it flies.

Can two people log in as the same username at the same time?

Yes, but only if you set the “Restrict Remote Desktop Services users to a single Remote Desktop Services session” policy to Disabled (Step 6). They’ll share the same profile and files, so use this for genuinely shared tool accounts, not as a way to skip on CAL costs.

Do I need a separate RD Licensing server?

For a small setup, no. The licensing role can sit on the same box. For 20 or more users, or anything you care about staying up, put it on a second server so rebooting the Session Host doesn’t knock out licence checks.

Does this work on Windows 10 or Windows 11 Pro?

No. Both are hard-limited to a single interactive session. Third-party patches like RDPWrap exist and they’ll technically get you multi-user, but they violate the Windows EULA and break on every cumulative update. If you need multi-user RDP, use Windows Server.

My users get disconnected after 15 minutes idle. How do I stop that?

That’s the default Session Time Limits policy. Same GPO tree as Step 5, under Session Time Limits. Set “Set time limit for active but idle Remote Desktop Services sessions” and “Set time limit for disconnected sessions” to whatever suits you. Just don’t set them to Never on a public-facing box, or stale sessions will pile up.