windows-iac-vm-tooling/docs/07-advanced/evaluation.md

⏰ 90-Day Evaluation Management

Overview

Windows Evaluation editions expire after 90 days. This document explains the expiration mechanism and provides strategies for managing it in your automation pipeline.

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Understanding Evaluation Expiration

flowchart LR
    subgraph Timeline["90-Day Timeline"]
        Start[Install Day 0] --> Day30[Day 30] --> Day60[Day 60] --> Day90[Day 90 - Expiration]
    end
    
    subgraph States["System States"]
        Active[✅ Active] --> Warning[⚠️ Warning 15 days] --> Expired[❌ Expired]
    end
    
    Timeline --> States
    
    style Timeline fill:#e3f2fd
    style States fill:#e8f5e9

Phase	Duration	Status
Full Activation	Days 0-89	✅ Fully functional
Warning Period	Days 90-104	⚠️ Countdown warnings
Grace Period	Days 105-180	⏳ Extended grace
Expired	Day 181+	❌ System stops

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Expiration Methods

Method 1: Rearm (Manual/Scripted)

The slmgr /rearm command resets the activation timer.

# Run as Administrator
slmgr /rearm

# Reboot required
shutdown /r /t 0

Limits:

• Maximum 3 rearm attempts per installation
• Each rearm resets to 90 days
• Total: 360 days maximum

Method 2: Packer Rebuild (Recommended)

The recommended approach is to rebuild the golden image monthly.

flowchart TB
    subgraph Monthly["Monthly Schedule"]
        direction LR
        Week1[Week 1: Packer Build] --> Week2[Week 2-4: Use Template]
    end
    
    subgraph Process["Rebuild Process"]
        Destroy[Destroy Old Template] --> Create[Create New Template] --> Verify[Test New Template]
    end
    
    Monthly --> Process
    
    style Monthly fill:#e3f2fd
    style Process fill:#e8f5e9

Benefits:

• Fresh timer each month
• Latest Windows updates baked in
• Consistent baseline
• No rearm limitations

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Implementation Strategy

Automated Monthly Rebuild

Configure a scheduled workflow in Forgejo:

# .forgejo/workflows/monthly-rebuild.yml
name: Monthly Template Rebuild
on:
  schedule:
    - cron: '0 0 1 * *'  # First day of each month at midnight

jobs:
  rebuild-template:
    runs-on: ubuntu-latest
    steps:
      - name: Checkout
        uses: actions/checkout@v3
      
      - name: Build New Template
        run: |
          cd packer
          packer build -timestamp-ui windows.pkr.hcl
      
      - name: Cleanup Old Template
        run: |
          # Script to remove template older than 45 days
          ./scripts/cleanup-old-templates.sh --older-than 45d

Rebarm as Backup

For emergency extension:

# emergency-rearm.ps1
# Run via Ansible or manually

if ((slmgr /dlv) -match "Remaining: 0") {
    Write-Host "Rearming system..."
    slmgr /rearm
    shutdown /r /t 0
} else {
    Write-Host "Not yet expired, no action needed"
}

---

Monitoring Expiration

Check Current Status

# Method 1: slmgr
slmgr /dlv

# Method 2: PowerShell
(Get-CimInstance -Query "SELECT * FROM SoftwareLicensingProduct WHERE PartialProductKey IS NOT NULL").RemainingGracePeriod

Automated Monitoring Script

#!/bin/bash
# check-expiration.sh - Run via Ansible monthly

VM_ID="9000"
PROXMOX_HOST="la-vmh-07"

# Get VM's Windows activation status
ssh root@$PROXMOX_HOST "qm agent $VM_ID exec-win32 powershell -Command '(Get-CimInstance -Query \"SELECT * FROM SoftwareLicensingProduct WHERE PartialProductKey IS NOT NULL\").RemainingGracePeriod'"

# Alert if less than 7 days
if [ $DAYS_REMAINING -lt 7 ]; then
    echo "⚠️ ALERT: Template expires in $DAYS_REMAINING days"
    # Send notification
fi

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Best Practices

Practice	Description	Priority
Monthly rebuild	Schedule automatic Packer build	🔴 High
Monitor expiration	Check status weekly	🟡 Medium
Test new templates	Verify before production use	🔴 High
Document rebuilds	Log template versions	🟢 Low

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Troubleshooting

Issue	Cause	Solution
Rearm failed	Already rearmed 3 times	Rebuild with Packer
VM won't boot after rearm	Activation issues	Rebuild template
Updates not installing	WSUS offline	Include updates in Packer build

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Next Steps

Goal	Next Document
View troubleshooting	Troubleshooting
Configure pipeline	Forgejo Workflows
View architecture	Architecture Overview

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