Is it possible to simulate a dual load balanced server configuration on VMWare pretty easily?

Is there free load balancing software out there that I could use for this?

I'm using Windows Server Standard 2008.

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I've seen this done in production using Windows Load Balancing. It works perfectly - no magic or simulation is required since it works at the OS level.

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A good and free load balancing choice is pen. If you can access a network port on your VM you can load balance it with pen. VMWare absolutely supports access to network ports.

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I use pen for load balancing under VMware. There's a VMware appliance which you can download and push it into VMware. It takes a little work to get it into ESX. There's info in the forum about how to do this. vmware.com/appliances/directory/300 – mrdenny Sep 24 '09 at 21:07
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Yes, yes you can - depends on your LB mechanism but you can have two VMs pointing their DG at another VM which is acting as a LB (or caching etc.). It wouldn't matter what OS, it's really just a layer 3 thing really.

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