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Installing Caddy on Windows

Overview​

Caddy is a powerful, enterprise-ready web server with automatic HTTPS that makes serving your sites easy. This comprehensive guide covers installation and configuration on Windows systems with proper security configurations, service management, and Cloudflare integration.

What is Caddy?​

Caddy is a modern web server that provides:

  • Automatic HTTPS: SSL certificates managed automatically
  • Reverse Proxy: Route traffic to backend applications
  • Static File Serving: Serve websites and files efficiently
  • Plugin System: Extend functionality with plugins
  • Easy Configuration: Simple, readable configuration files

Key Features​

  • Zero-Config HTTPS: Automatic SSL certificate provisioning and renewal
  • HTTP/2 and HTTP/3: Modern protocol support out of the box
  • Reverse Proxy: Load balancing and backend routing
  • Static Site Hosting: Perfect for modern web applications
  • Plugin Ecosystem: DNS providers, authentication, and more

Prerequisites​

Before beginning the installation, ensure your system meets the following requirements:

System Requirements​

  • Operating System: Windows 10/11 or Windows Server 2019/2022
  • Architecture: x86_64 (64-bit)
  • RAM: Minimum 512MB (1GB+ recommended)
  • Disk Space: At least 100MB free space
  • Network: Internet connection for downloading and certificates

Required Permissions​

  • Administrator access for installation and service setup
  • Port access: Ability to bind to ports 80 and 443
  • Firewall configuration permissions

Installation​

Step 1: Download Caddy​

  1. Visit the Caddy Download Page: Caddy Download Builder

  2. Select Required Plugins (if needed):

    • For Cloudflare: github.com/caddy-dns/cloudflare
    • For DuckDNS: github.com/caddy-dns/duckdns

  3. Download for Windows:

    • Select Windows as the operating system
    • Select amd64 architecture
    • Download the binary

Step 2: Install Caddy​

  1. Create Tools Directory: Create directory structure

    New-Item -ItemType Directory -Path "C:\Tools\Caddy" -Force

  2. Extract and Install: Move downloaded caddy.exe to Tools directory

    Move-Item "Downloads\caddy.exe" "C:\Tools\Caddy\caddy.exe"

    Add to system PATH

    [Environment]::SetEnvironmentVariable("PATH", $env:PATH, [EnvironmentVariableTarget]::Machine)

  3. Verify Installation: Check Caddy version

    caddy version

Configuration​

Step 3: Basic Configuration​

  1. Create Caddyfile: Navigate to Caddy directory

    cd C:\Tools\Caddy

    Create basic Caddyfile

    New-Item -ItemType File -Path "Caddyfile"

  2. Basic Caddyfile Example:

    # Replace with your domain
     app.example.com {
         reverse_proxy localhost:3000
     }

Step 4: Running Caddy​

Manual Execution​

Navigate to Caddy directory

cd C:\Tools\Caddy

Run Caddy with configuration

./caddy run --config Caddyfile
caution

Accept both permissions if Windows Firewall prompts appear upon first run.

For production use, install Caddy as a Windows service:

Install as Windows service

caddy run --config C:\Tools\Caddy\Caddyfile --service install

Start the service

caddy start --service

Check service status

caddy status --service

Cloudflare Integration​

If you're using Cloudflare for DNS management:

Step 5: Setting up A Name Record​

  1. Open Cloudflare Dashboard: https://dash.cloudflare.com/

  2. Click DNS on the sidebar:

image

  1. Click Add a Record:

image

  1. Get your external IP from https://ipchicken.com/:

image

  1. Click Save

Step 6: Getting an API Key​

  1. Go to Overview in the right-hand menu:

image

  1. Scroll down and click "Get API Token":

image

  1. Click Create a Token:

image

  1. Select Custom Token:

image

  1. Configure Token Permissions:

image

  1. Copy your token:

image

Step 7: Running Cloudflare DDNS​

danger

If Using a VPN, following the steps below will break your DNS configuration and make your services unreachable

Download CloudFlare DDNS​

  1. Download Cloudflare DDNS: CloudFlare DDNS
    • Choose the package for your system: Most likely cloudflare-ddns_v1.1.1_windows_amd64.zip

Assets

  1. Extract to directory: C:\Tools\CloudflareDDNS

    • The Filepath after being unzipped should be as follows. 
      └── C:/
          └── Tools/
              └── CloudFlareDDNS/
                  └── cloudflare-ddns.exe

Download and Setup DDNS Scripts​

  1. Open a Terminal Window:

    • Right click any blank space in the CloudFlareDDNS Directory.
    • Click Open in Terminal

  2. Download the automated scripts using Powershell:

    curl -o cloudflare-ddns-automated.bat https://raw.githubusercontent.com/DevilsDesigns/DemonWarriorTechDocs/main/scripts/Cloudflare/cloudflare-ddns-automated.bat
    curl -o log-cleanup.bat https://raw.githubusercontent.com/DevilsDesigns/DemonWarriorTechDocs/main/scripts/Cloudflare/log-cleanup.bat

Configure the DDNS Script​

  1. Open cloudflare-ddns-automated.bat in a text editor and change these lines:

    cloudflare-ddns-automated.bat
    REM Configuration - Edit these values
    set CF_TOKEN=your-cloudflare-api-token
    set CF_ZONE=yourdomain.com
    REM Note: CF_ZONE should be your root domain (e.g., demonwarriortech.com)

    REM Dry-run mode - set to "true" to see what would be updated without making changes
    set DRY_RUN=true
    info

    Note: DRY_RUN is enabled by default for safety reasons. This allows you to test the configuration without making actual DNS changes.

  2. Replace the configuration values:

    • CF_TOKEN: Your CloudFlare API token from Step 6
    • CF_ZONE: Your root domain (e.g., demonwarriortech.com)
    • Keep DRY_RUN=true for initial testing

Test the Configuration​

  1. Run the script as Administrator:

    • Right-click on cloudflare-ddns-automated.bat
    • Select "Run as administrator"
    • Accept any Windows Firewall prompts

  2. Check the log file at ./logs/cloudflare-ddns.log for entries like:

    ======================================== 
    [2025-09-20 18:26:11] Starting CloudFlare DDNS update... 
    [2025-09-20 18:26:11] Detecting current public IP... 
    [2025-09-20 18:26:12] DEBUG: Primary IP service failed, trying fallback... 
    [2025-09-20 18:26:12] DEBUG: curl services failed, trying PowerShell fallback... 
    [2025-09-20 18:26:13] Current public IP: 203.0.113.42 
    [2025-09-20 18:26:13] Getting CloudFlare Zone ID for demonwarriortech.com... 
    [2025-09-20 18:26:15] DEBUG: Zone ID: a437cf***********497 
    [2025-09-20 18:26:15] Discovering all A records in zone... 
    [2025-09-20 18:26:17] Analyzing A records for updates... 
    [2025-09-20 18:26:18] DEBUG: Found A record: adguard.demonwarriortech.com -> 198.51.100.10 (Proxied: True)
    [2025-09-20 18:26:18] INFO: Record needs update: adguard.demonwarriortech.com (198.51.100.10 -> 203.0.113.42)
    [2025-09-20 18:26:18] DEBUG: Found A record: jellyfin.demonwarriortech.com -> 198.51.100.10 (Proxied: False)

  3. Verify the results:

    • If the new IP matches your current IP, you're ready to proceed
    • Change set DRY_RUN=true to set DRY_RUN=false in the script
    • Run the script again as Administrator to apply the changes

Step 8: Schedule Automatic Updates​

  1. Set up Task Scheduler for automatic execution:

    📋 Manual Task Scheduler Setup Instructions​

    Step 1: Open Task Scheduler​
    1. Press Win + R, type taskschd.msc, press Enter
    2. Or search "Task Scheduler" in Start menu
    Step 2: Create Task​
    1. In the right panel, click "Create Task..." (not "Create Basic Task")
    2. Name: CloudFlare DDNS Auto Update
    3. Description: Automatically updates CloudFlare DDNS every 5 minutes and at startup

Create Task

Step 3: General Tab Settings​
  • ✅ Run whether user is logged on or not
  • ✅ Run with highest privileges
  • Configure for: Windows 10/11

Task General

Step 4: Triggers Tab​

Click "New..." twice to create 2 triggers:

Trigger 1 - At Startup:

  • Begin the task: At startup
  • Delay task for: 1 minute
  • ✅ Enabled

Trigger 2 - Every 5 Minutes:

  • Begin the task: On a schedule
  • Settings: One Time, start today at current time
  • ✅ Repeat task every: 5 minutes
  • for a duration of: Indefinitely
  • ✅ Enabled

Task Trigger 1 Task Trigger 2

Step 5: Actions Tab​

Click "New...":

  • Action: Start a program
  • Program/script: C:\Tools\CloudFlareDDNS\cloudflare-ddns-automated.bat
  • Start in: C:\Tools\CloudFlareDDNS

Task Actions

Step 6: Conditions Tab​
  • ✅ Start only if a network connection is available
  • ❌ Start the task only if the computer is on AC power (uncheck this)
  • ❌ Stop if the computer switches to battery power (uncheck this)

Task Conditions

Step 7: Settings Tab​
  • ✅ Allow task to be run on demand
  • ✅ Run task as soon as possible after a scheduled start is missed
  • ✅ If the running task does not end when requested, force it to stop
  • If the task is already running: Do not start a new instance

Task Settings

Step 8: Finish​
  1. Click OK
  2. Enter your Windows password when prompted
  3. Task is now created!

Test the task: Right-click the task → "Run"
Check logs: C:\Tools\CloudFlareDDNS\logs\cloudflare-ddns.log

Task Run

Your DDNS will now update automatically every 5 minutes! 🚀

Maintenance​

  1. Log cleanup (optional):

    • Run log-cleanup.bat periodically to manage log file sizes
    • Or set up another scheduled task to run it weekly

  2. Monitor the service:

    • Check logs regularly: C:\Tools\CloudFlareDDNS\logs\cloudflare-ddns.log
    • Verify DNS records are updating correctly in CloudFlare dashboard
    • Test your domain resolution periodically

Service Management​

Windows Service Commands​

Start Caddy service

net start caddy

Stop Caddy service

net stop caddy

Restart Caddy service

net stop caddy && net start caddy

Check service status

sc query caddy

Configuration Management​

Test configuration before applying

caddy validate --config C:\Tools\Caddy\Caddyfile

Format Caddyfile

caddy fmt --overwrite C:\Tools\Caddy\Caddyfile

Reload configuration

caddy reload --config C:\Tools\Caddy\Caddyfile

View current configuration

caddy config --config C:\Tools\Caddy\Caddyfile

Troubleshooting​

Common Issues​

Issue 1: Service Won't Start​

Check Windows Event Logs

Get-EventLog -LogName Application -Source Caddy -Newest 10

Check service status

sc query caddy

Common causes:

  • Configuration syntax errors
  • Permission issues
  • Port conflicts

Solution: Validate configuration

caddy validate --config C:\Tools\Caddy\Caddyfile

Check file permissions

Get-Acl C:\Tools\Caddy\Caddyfile

Test manual execution

Move to Caddy.exe Folder Directory

cd C:\Tools\Caddy

Run Caddy command inside Caddy folder

./caddy run --config Caddyfile

Issue 2: Firewall Blocking​

Check Windows Firewall rules

Get-NetFirewallRule -DisplayName "*Caddy*"

Add firewall rules if needed

New-NetFirewallRule -DisplayName "Caddy HTTP" -Direction Inbound -Protocol TCP -LocalPort 80 -Action Allow
New-NetFirewallRule -DisplayName "Caddy HTTPS" -Direction Inbound -Protocol TCP -LocalPort 443 -Action Allow

Issue 3: Certificate Issues​

Check certificate status

caddy list-certificates

Clear certificate cache if needed

Remove-Item -Recurse -Force "$env:APPDATA\Caddy\certificates"

Security Best Practices​

File Permissions​

Secure Caddy directory

$acl = Get-Acl "C:\Tools\Caddy"
$acl.SetAccessRuleProtection($true, $false)
$accessRule = New-Object System.Security.AccessControl.FileSystemAccessRule("Administrators","FullControl","Allow")
$acl.SetAccessRule($accessRule)
Set-Acl "C:\Tools\Caddy" $acl

Firewall Configuration​

Enable Windows Firewall

Set-NetFirewallProfile -Profile Domain,Public,Private -Enabled True

Configure specific rules

New-NetFirewallRule -DisplayName "Caddy HTTP" -Direction Inbound -Protocol TCP -LocalPort 80 -Action Allow
New-NetFirewallRule -DisplayName "Caddy HTTPS" -Direction Inbound -Protocol TCP -LocalPort 443 -Action Allow

Next Steps​

Advanced Configuration​

  1. Explore advanced directives: header, encode, rate_limit
  2. Set up monitoring: Windows Performance Counters, health checks
  3. Configure logging: Custom log formats and Windows Event Log integration
  4. Implement security headers: HSTS, CSP, X-Frame-Options

Integration Examples​

  • IIS Integration: Run alongside IIS for specific applications
  • Docker Desktop: Reverse proxy to Windows containers
  • Load balancing: Distribute traffic across multiple Windows servers
  • API gateway: Route and transform API requests

Resources​

Summary​

You have successfully installed Caddy on Windows with:

✅ Professional installation with proper directory structure
✅ Windows service integration for automatic startup
✅ Automatic HTTPS capability with zero configuration
✅ Cloudflare integration for dynamic DNS management
✅ Security best practices - Proper permissions and firewall rules
✅ Production-ready configuration - Enterprise deployment ready

Your Caddy installation is now ready for production use with automatic HTTPS, robust security, and professional service management on Windows.

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