When configuring Windows web servers in enterprise environments, administrators often face a fundamental architectural decision: whether to integrate web servers into the existing Active Directory (AD) domain or maintain them in an isolated workgroup configuration. This choice significantly impacts both security posture and operational workflows.

Joining web servers to an AD domain offers several security advantages:

• Centralized authentication via Kerberos or NTLM
• Group Policy enforcement for consistent security baselines
• Centralized auditing through Event Forwarding
• Simplified certificate management via Autoenrollment

However, domain membership also expands the attack surface. A compromised web server could potentially be used to attack other domain members. Consider this PowerShell snippet for constrained delegation configuration:

# Configure constrained delegation for web service account
Set-ADComputer -Identity WEBSERVER01 
-Add @{'msDS-AllowedToDelegateTo'=@('HTTP/appserver.corp.com','HTTP/internalapp.corp.com')}

Maintaining web servers in a separate workgroup provides stronger isolation but increases management overhead:

• Local account management required for all administrative access
• Manual configuration of security policies on each server
• No centralized authentication mechanism

Here's how to configure local administrative accounts consistently across workgroup servers:

# Create local admin account with strong password
$Password = ConvertTo-SecureString "ComplexP@ssw0rd!" -AsPlainText -Force
New-LocalUser -Name "WebAdmin" -Password $Password -Description "Web Server Management Account"
Add-LocalGroupMember -Group "Administrators" -Member "WebAdmin"

For environments requiring both security and manageability, consider these mixed strategies:

1. Read-Only Domain Controller (RODC): Place web servers in a perimeter network with an RODC that contains only necessary accounts.
2. Administrative Tiering: Implement Privileged Access Workstations (PAWs) and separate administrative accounts for web servers.
3. Group Policy Preferences: Use item-level targeting to apply specific policies only to web servers.

Example GPO configuration for web server hardening:

# Audit policy for web servers
auditpol /set /category:"Account Logon","Logon/Logoff","Object Access","Policy Change","Privilege Use","Detailed Tracking","System" /success:enable /failure:enable

Evaluate your specific requirements for:

• Patch management integration with WSUS or SCCM
• Monitoring and alerting systems
• Content deployment workflows
• Compliance reporting needs

For automated configuration in either scenario, consider this DSC configuration:

Configuration SecureWebServer
{
    Node "WEBSERVER01"
    {
        WindowsFeature IIS
        {
            Ensure = "Present"
            Name = "Web-Server"
        }
        
        Registry DisableWeakCiphers
        {
            Ensure = "Present"
            Key = "HKLM:\SYSTEM\CurrentControlSet\Control\SecurityProviders\SCHANNEL\Ciphers\RC4 128/128"
            ValueName = "Enabled"
            ValueData = "0"
            ValueType = "Dword"
        }
    }
}

Use this matrix to guide your architecture choice:

When architecting Windows web server infrastructure, administrators often face a critical design decision: whether to join web servers to an Active Directory (AD) domain or keep them in an isolated workgroup. This choice significantly impacts both security posture and operational workflows.

Domain membership offers several security advantages through centralized management:

• Group Policy Objects (GPOs) for consistent security baselines
• Centralized authentication via Kerberos
• Audit trail integration with SIEM systems

Example PowerShell for applying web server hardening GPOs:

# Apply specific GPOs to web server OU
Invoke-GPUpdate -Computer "WEB01" -RandomDelayInMinutes 0 -Force
Get-GPOReport -Name "WebServer Hardening" -ReportType Html -Path "C:\reports\webserver_gpo.html"

For internet-facing servers, workgroup configuration provides:

• Reduced attack surface by eliminating domain trust relationships
• Prevention of lateral movement via compromised domain credentials
• Simplified compliance boundaries for PCI DSS and similar frameworks

A balanced solution might involve:

# Example Just-in-Time Admin configuration for workgroup servers
$jitPolicy = @{
    Name               = "WebServer-Admins"
    Enabled            = $true
    Duration           = "4"
    ActivationStart    = (Get-Date).AddHours(1)
    ActivationEnd      = (Get-Date).AddHours(5)
    Principals         = "CONTOSO\Web-Admins"
}
New-PimConditionalAccessPolicy @jitPolicy

Regardless of configuration, implement:

# Sample Windows Event Forwarding configuration for web servers
<Subscription>
    <Query>
        <Select Path="Security">*[System[(EventID=4624 or EventID=4625)]]</Select>
        <Select Path="System">*[System[(Level=1 or Level=2)]]</Select>
    </Query>
    <ReadExistingEvents>true</ReadExistingEvents>
    <TransportName>HTTP</TransportName>
</Subscription>