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PowerShell Remoting in the Enterprise. What you need to know. Speaker. 9+ years experience in Microsoft-based IT Microsoft System Center 2012 R2 Windows PowerShell since 2007 Started writing VBscript in 2005 Worked in many enterprise environments with 10-70k+ systems. Why use remoting ?.

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  • 9+ years experience in Microsoft-based IT

  • Microsoft System Center 2012 R2

  • Windows PowerShell since 2007

    • Started writing VBscript in 2005

  • Worked in many enterprise environments with 10-70k+ systems

Why use remoting
Why use remoting?

  • Fan-out management of Windows Server systems

  • Desired State Configuration (DSC) in PowerShell v4

  • PowerShell Workflow

  • Interactive remote management (similar to SSH)

  • Quicker than RDP

How does remoting work
How does remoting work?



PowerShell Session

PowerShell Session



Windows Remote Management

Windows Remote Management


TCP 5986

TCP 5985




Remoting configuration
Remoting Configuration

SSL requires a “Server Authentication” certificate

  • Enable-PSRemoting -Force;

  • Set-WsmanQuickConfig -UseSSL;

  • Use Group Policy

Manual Configuration Process

Winrm service gpo configuration
WinRM Service GPO Configuration

Don’t leave listeners blank!

Windows powershell gpo settings
Windows PowerShell GPO Settings

  • Use either:

  • Remote Signed

  • Unrestricted

powershell.exe –ExecutionPolicy Bypass –File c:\path\to\script.ps1

Winrm client configuration
WinRM Client Configuration

  • Authentication

    • Basic

    • Negotiate

    • Kerberos

    • Client certificate mapping

    • Credential Security Support Provider (CredSSP)

  • TrustedHosts

  • DefaultPorts

TrustedHosts is useful in multi-forest, multi-domain, or workgroup environments. Special alias “<local>” for hostnames without dots “.”

Winrm client configuration1
WinRM Client Configuration

Winrm shell configuration
WinRM Shell Configuration

Set-Location –Path wsman:\localhost\shell;


Windows remote shell gpo configuration
Windows Remote Shell GPO Configuration

Windows Server 2012 Default Values

Quota Management for Remote Shells


Powershell remoting cmdlets
PowerShell Remoting Cmdlets

  • Enter-PSSession

  • New-PSSession

  • Remove-PSSession

  • Connect-PSSession

  • Invoke-Command

  • New-PSSessionConfigurationFile

  • about_Session_Configuration_Files

  • about_Session_Configurations

Cim cmdlets
CIM Cmdlets

Replace the WMI cmdlets in PowerShell v2.

  • Get-CimAssociatedInstance

  • Get-CimClass

  • Get-CimInstance

  • Get-CimSession

  • Invoke-CimMethod

  • New-CimInstance

  • New-CimSession

  • New-CimSessionOption

  • Register-CimIndicationEvent

  • Remove-CimInstance

  • Remove-CimSession

  • Set-CimInstance

Session configurations
Session Configurations

  • Restrict the commands that can be executed in a remote session

  • Restrict who can access the session configuration

  • Default session configurations can be removed or modified

  • Use Enable-PSRemoting to restore original configurations (after deleting)

Credential security support provider credssp
Credential Security Support Provider (CredSSP)



  • Allows double-hop scenario

  • Three types of credentials.PowerShell uses one.

    • Default credential

    • Saved credential

    • Fresh credential

  • Can be configured via GPO


  • CredSSP PowerShell Commands

  • Get-WSManCredSSP

  • Enable-WSManCredSSP

  • Disable-WSManCredSSP

Credssp group policy configuration
CredSSP Group Policy Configuration


  • Enable-PSWsmanCombinedTrace;

    • Get-WinEvent –Oldest $PSHome\Traces\pstrace.etl

  • Enable the Microsoft-Windows-WinRM/Operational event log

  • Read the error messages

  • Use Nmap to test ports (http://nmap.org)

    • nmap.exe –p5985,5986 server.domain.com

  • Use netstat –aon to ensure port is listening


  • Missing Service Principal Name (SPN) causes CredSSP connections to fail

  • Windows Firewall prevents communication (TCP 5985)

  • Windows Remote Management (WinRM) Listeners are empty in GPO configuration

  • SSL Certificate is expired or has mismatched DNS name in Subject Name field

  • Mismatching certificate thumbprints for WinRM“Service” and “Listener” configurations

    • Get-ChildItem -Path wsman:\localhost\Listeners\<HTTPSListener>;

    • Get-ChildItem –Path wsman:\localhost\service;

    • Remove-Item –Path HKLM:\Software\Microsoft\Windows\CurrentVersion\Wsman\Listener\*+HTTPS:certThumbprint

  • Restart PowerShell after Enable-WSManCredSSP -Role Client;

  • Incorrect permissions on $env:ProgramData\Microsoft\Crypto\RSA\MachineKeys prevents the WinRM service from reading the SSL certificate

  • Windows 2008: Missing Microsoft.PowerShell session configuration (use Enable-PSRemoting to resolve)

  • Use FQDN to connect to remote system with CredSSP or SSL

  • Certificate Revocation List (CRL) is outdated

    • Fix with: certutil.exe –CRL


  • Starting a remote session from within a remote session

  • Interactive command-line utilities don’t work well under remotingsessions

    • diskpart

    • nslookup

    • psexec

  • CredSSP is required to access network resources from a remote session

Built in variables
Built-in Variables

  • $PSSenderInfo – Use this automatic variable to explore the remote session configuration (authentication type, SSL, etc.)

  • $PSSessionOption – A preference variable that allows you to set the default remote session options