Basic security for Windows including RDP and SSH

Basic security configuration and measures for Windows including RDP and SSH management

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Here I have gathered some basic security measures that should be taken on every Windows installation. I have used these (and many more) on Windows 10, Windows 11, Windows Server 2016, Windows Server 2019 and Windows Server 2022.

Short description of operations:

What this guide is

This is a basic, getting started, guide ! After implementing these measures:

What this guide is not

Configure network adapters

For every network adapter go to Ethernet properties and disable unused protocols. For most computers I use only:

Sharing is needed only for file servers and printer servers !

Select Internet Protocol Version 4 (TCP/IPv4) and click the Properties button then click the Advanced button and in the WINS tab:

Disable all unused network adapters

Configure the firewall

For Windows clients you need:

For servers:

Windows PC

Make sure that you have at least some rules for Ping and RDP. Check the following code if want to add rules with PowerShell (replace 192.168.5.3 before use !):

$mngStations = @("192.168.5.3")
$icmpAccess = @("LocalSubnet", "192.168.5.3")

New-NetFirewallRule -DisplayName 'StartRule-Ping' -Enabled True -Direction Inbound -Action Allow -Protocol ICMPv4 -IcmpType 8 -RemoteAddress $icmpAccess

New-NetFirewallRule -DisplayName 'StartRule-RDP' -Enabled True -Direction Inbound -Action Allow -Protocol TCP -LocalPort 3389 -RemoteAddress $mngStations

New-NetFirewallRule -DisplayName 'StartRule-SSH' -Enabled True -Direction Inbound -Action Allow -Protocol TCP -LocalPort 22 -RemoteAddress $mngStations -Program '%SystemRoot%\system32\OpenSSH\sshd.exe'

Enable the firewall for all profiles with these settings:

Now delete any other Inbound and Outbound rule.

Windows File server example

$fsClients = @("LocalSubnet")

New-NetFirewallRule -DisplayName 'StartRule-FS' -Enabled True -Direction Inbound -Action Allow -Protocol TCP -LocalPort 445 -RemoteAddress $fsClients

Windows HTTP / HTTPS server example

$httpClients = @("LocalSubnet")

# for HTTP
New-NetFirewallRule -DisplayName 'StartRule-HTTP' -Enabled True -Direction Inbound -Action Allow -Protocol TCP -LocalPort 80 -RemoteAddress $httpClients

# for HTTPS
New-NetFirewallRule -DisplayName 'StartRule-HTTPS' -Enabled True -Direction Inbound -Action Allow -Protocol TCP -LocalPort 443 -RemoteAddress $httpClients

Accounts

Use long and strong passwords, preferably random generated. Use a password manager and do not reuse the passwords.

Forget about password expiration policy ! NIST removed the references to periodic password changes in its password guidance since 2017 ! Password expiration policy is not only outdated, is doing more harm than good ! Search the web and use your mind.

Not in the scope of this guide but use MFA at least for the accounts with administrative rights.

As a best practice, add an administrative account for every local administrator and disable the built-in Administrator account.

For domain-joined computers keep one local administrator account and use it only for emergency cases. Ideally, the local emergency administrator should be protected by different passwords (long, strong and random generated) on every computer.

Not in the scope of this guide but maybe Microsoft’s Local Administrator Password Solution may worth a try. Check Step-by-Step Guide: How to Configure Microsoft Local Administrator Password Solution (LAPS)

OpenSSH server installation and configuration

OpenSSH installation

# install the client and the server
Get-WindowsCapability -Online | Where-Object Name -like 'OpenSSH.*' |
ForEach-Object -Process {
    if ($_.State -ne [Microsoft.Dism.Commands.PackageFeatureState]::Installed) {
        Write-Host "Installing" $_.Name
        Add-WindowsCapability -Online -Name $_.Name
    }
}

# start the service and set it to start automatically
Start-Service -Name sshd
Set-Service -Name sshd -StartupType 'Automatic'

# optional, set the default shell to be powershell.exe
New-ItemProperty -Path "HKLM:\SOFTWARE\OpenSSH" -Name DefaultShell -Value "$env:SystemRoot\System32\WindowsPowerShell\v1.0\powershell.exe" -PropertyType String -Force

Public key authentication

If you do not have a key pair or wish to generate a new one use execute:

ssh-keygen -t ed25519 -f my_new_ed25519_key -C "This is my new shiny key"
cat my_new_ed25519_key.pub

To add the key:

# set the value from my_new_ed25519_key.pub
$authorizedKey = "ssh-ed25519 AAA..............................................................xyz This is my new shiny key"

# add it to `administrators_authorized_keys` file
Add-Content -Force -Path $env:ProgramData\ssh\administrators_authorized_keys -Value "$authorizedKey"

# make sure the permissions for `administrators_authorized_keys` are correct
icacls.exe "$env:ProgramData\ssh\administrators_authorized_keys" /inheritance:r /grant "Administrators:F" /grant "SYSTEM:F"

OpenSSH configuration

To see if the algorithms from the next conf file are supported use:

ssh -Q cipher
ssh -Q mac
ssh -Q kex

Edit %programdata%\ssh\sshd_config and add these to the beginning of the file:

Protocol 2
PubkeyAuthentication yes
PasswordAuthentication no
AuthenticationMethods publickey

KexAlgorithms curve25519-sha256@libssh.org,curve25519-sha256
Ciphers chacha20-poly1305@openssh.com,aes256-gcm@openssh.com
MACs hmac-sha2-512-etm@openssh.com,hmac-sha2-256-etm@openssh.com

Regenerate host keys

# delete actual keys
Remove-Item -Path $env:ProgramData\ssh\ssh_host_*_key;
Remove-Item -Path $env:ProgramData\ssh\ssh_host_*_key.pub

# restart SSHD service. It will regenerate the keys
Restart-Service -Name sshd

To display the SHA256 fingerprint for the new hosts’s ed25519 key use:

ssh-keygen -lf $env:ProgramData\ssh\ssh_host_ed25519_key

Note: Installing OpenSSH may require a restart. If the connection is not working then try again after restart.

Check SSH connection

Connect to the server with your key:

# for local accounts added to the local Administrators group
ssh localAdmin@ip_of_the_server -i my_new_ed25519_key

#for domain accounts added to the local Administrators group
#ssh account@domain@ip_of_the_server -i my_new_ed25519_key

First connection

If you never connected before to this host you will receive a warning like this:

The authenticity of host '..............' can't be established.
ED25519 key fingerprint is SHA256:Aaaa........................................
Are you sure you want to continue connecting (yes/no/[fingerprint])?

The fingerprint of the key should be the one you’ve got in the Regenerate host keys section. If is the same type yes.

Connection after the host keys were regenerated

If you have regenerated the host keys you will receive a warning like this:

@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@
@    WARNING: REMOTE HOST IDENTIFICATION HAS CHANGED!     @
@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@@
IT IS POSSIBLE THAT SOMEONE IS DOING SOMETHING NASTY!
Someone could be eavesdropping on you right now (man-in-the-middle attack)!
It is also possible that a host key has just been changed.
The fingerprint for the ED25519 key sent by the remote host is
SHA256:Aaaa........................................
Please contact your system administrator.
Add correct host key in ................./known_hosts to get rid of this message.
Offending ED25519 key in ................./known_hosts
  remove with:
  ssh-keygen -f "................./known_hosts" -R "................."
ED25519 host key for ............... has changed and you have requested strict checking.
Host key verification failed.

Remove the key as it says (ssh-keygen -f "..." -R "...") and connect again.

Tunnel RDP through SSH

On your management computer, open a tunnel to the destination computer:

# for local accounts added to the local Administrators group
ssh -L 9999:127.0.0.1:3389 localAdmin@ip_of_the_server -i my_new_ed25519_key

#for domain accounts added to the local Administrators group
#ssh -L 9999:127.0.0.1:3389 account@domain@ip_of_the_server -i my_new_ed25519_key

To connect to the server with tunneled RDP use 127.0.0.1:9999 as your destination address.

On the remote server, executing netstat -bn will show the connections:

TCP  127.0.0.1:3389     127.0.0.1:49746             ESTABLISHED
TermService
[svchost.exe]

TCP  127.0.0.1:49746    127.0.0.1:3389              ESTABLISHED
[sshd.exe]

TCP  192.168.server:22  192.168.managementPC:57402  ESTABLISHED
[sshd.exe]

Now you can delete / disable the RDP access rule (StartRule-RDP) and connect only using SSH tunnels. Removing that rule will block you to use RDP directly but will also block anyone who may try to attack it.

Domain-joined computers

You should have at least an Organizational Unit (OU) for workstations and OUs for servers. GPOs can be applied to following Active Directory containers: site, domain, organizational unit.

Access GPO

Create a GPO for access. Under Computer Configuration/ Policies make these settings:

Windows Settings
    Security Settings
        Local Policies / User Rights Assignment
            Allow log on through Terminal Services : add here the accounts that are allowed to connect through RDP
        Restricted Groups
            BUILTIN\Administrators : add here the users that should be members of the local Administrators group
Administrative Templates
    Windows Components / Remote Desktop Services / Remote Desktop Session Host / Connections
        Allow users to connect remotely by using Remote Desktop Services : Enabled
        Restrict Remote Desktop Services users to a single Remote Desktop Services session : Enabled
        Select RDP transport protocols : Enabled, Transport Type = Use only TCP
        Set rules for remote control of Remote Desktop Services user sessions : Enabled, Full Control without user's permission
    Windows Components / Remote Desktop Services / Remote Desktop Session Host / Security
        Require secure RPC communication : Enabled
        Require use of specific security layer for remote (RDP) connections : Enabled, Security Layer = SSL
        Require user authentication for remote connections by using Network Level Authentication : Enabled
        Set client connection encryption level : Enabled, Encryption Level = High Level

Apply this GPO to the OUs with computers and servers.

Firewall GPOs

You should create GPOs with firewall rules for every server group - grouping based on exposed network services / ports - and one for PCs.

The basic skeleton is this:

Windows Settings
    Security Settings
        Windows Firewall with Advanced Security
            Domain Profile Settings, Private Profile Settings and Public Profile Settings
                Firewall state:	On
                Inbound connections: Block
                Outbound connections: Allow
                Apply local firewall rules: No
                Apply local connection security rules: No
                Display notifications: Yes
                Allow unicast responses: No
                Log dropped packets: Yes
                Log successful connections: Yes
                Log file path: %systemroot%\system32\logfiles\firewall\pfirewall.log
                Log file maximum size (KB): 4096
            Inbound Rules
                # add a rule for OpenSSH access
                # add a rule for RDP access
                # add a rule for ICMP Echo Request
Administrative Templates
    Network / Network Connections / Windows Defender Firewall / Domain Profile
        Windows Defender Firewall: Allow logging : Enabled
            Log dropped packets: Enabled
            Log successful connections: Enabled
            Log file path and name: %systemroot%\system32\logfiles\firewall\pfirewall.log
            Size limit (KB): 4096
        Windows Defender Firewall: Prohibit notifications : Disabled
        Windows Defender Firewall: Prohibit unicast response to multicast or broadcast requests : Enabled
        Windows Defender Firewall: Protect all network connections : Enabled

and is OK for the computers that does not offer / expose network services. Apply this to the OUs for computers.

After OpenSSH configuration and RDP through SSH works, the RDP access rule can be eliminated. As I have said before, removing that rule will block you to use RDP directly but will also block anyone who may try to attack it.

For every server group create dedicated firewall GPOs, based on previous skeleton, and add the required inbound rules. Apply these to the OUs for servers.

Closing words

This article cover some minimal security settings and advices that will improve the security configuration of Windows hosts. In real life you should use scripts to configure the systems and you should take more measures to improve your security posture.

The configuration of OpenSSH server can be improved, but that is another article.

The configuration of your SSH client should be checked. Disabling agent forwarding will protect you from MITM attacks.

The GPOs are minimal. There are a lot more settings that can improve the security of Windows hosts.

Tags:RDPSSHWindows ServerWindowsOpenSSH

Category:System Administration

Created 2022-09-16

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