How to Redirect Traffic from One IP to Another in Windows Server 2008 Using Route Command


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When migrating servers, hardcoded IP addresses in legacy applications can cause headaches. Here's how to seamlessly redirect traffic from an old IP (83.83.83.83) to a new server (66.221.24.31) in Windows Server 2008.

The most reliable method is using Windows' built-in route command:

route add 83.83.83.83 mask 255.255.255.255 66.221.24.31 -p

This command does the following:

  • Creates a persistent route (-p flag) that survives reboots
  • Directs all traffic for 83.83.83.83 to 66.221.24.31
  • Uses a full subnet mask (255.255.255.255) for precise targeting

After adding the route, verify it works:

ping 83.83.83.83
tracert 83.83.83.83
route print

For more complex scenarios, consider:

1. Windows Firewall with Advanced Security

Create a NAT rule:

netsh interface portproxy add v4tov4 listenaddress=83.83.83.83 connectaddress=66.221.24.31

2. Editing the Hosts File

For name resolution redirection:

# Edit C:\Windows\System32\drivers\etc\hosts
66.221.24.31    old.server.name
  • Run command prompt as Administrator
  • Check for conflicting routes with route print
  • Disable IPv6 if encountering unexpected behavior
  • For web applications, ensure IIS bindings are properly configured

If you need to redirect:

  • Specific ports only
  • HTTP/HTTPS traffic
  • Between different subnets

You might need to implement a full DNS migration plan or use a load balancer configuration.

During server migration projects, we often encounter legacy applications with hardcoded IP addresses that can't be easily modified. This creates connectivity issues when decommissioning old servers. Here's a robust solution using Windows Server 2008's routing capabilities.

The most reliable method is adding a static route to your Windows Server 2008 routing table:

route add 83.83.83.83 mask 255.255.255.255 66.221.24.31 -p

This command:

  • Permanently (-p flag) redirects all traffic destined for 83.83.83.83
  • Uses a full subnet mask (255.255.255.255) for single IP redirection
  • Sends traffic to the new server at 66.221.24.31

After adding the route, verify it exists in your routing table:

route print

Look for an entry similar to:

Network Destination    Netmask      Gateway       Interface  Metric
83.83.83.83            255.255.255.255 66.221.24.31    66.221.24.31     1

For more complex scenarios, consider configuring Network Address Translation in Routing and Remote Access Service:

netsh routing ip nat add interface name="Public" mode=full
netsh routing ip nat add addressrange 83.83.83.83 83.83.83.83
netsh routing ip nat add addressmapping 83.83.83.83 66.221.24.31

After implementation, test with:

ping 83.83.83.83
tracert 83.83.83.83

Both should show responses coming from 66.221.24.31.

  • Ensure firewall rules allow traffic between the IPs
  • Test application functionality thoroughly after redirection
  • Document all changes for future reference
  • Consider DNS alternatives for long-term solutions