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In my experience both IIS Web Farm Framework and MSDeploy is doing a really poor job of managing configurations between servers.

While the idea behind the Web Farm Framework and MSDeploy is awesome, I don't think any of those two have done a good job of doing the task. Of all the setups where I've tried to use either Web Farm Framework or MSDeploy, it has failed, or at best, run very unstable. Usually I have to revert to manually configuring servers and mirroring files, which is less than optimal in larger setups.

So I wonder if there is any IIS configuration management on the market which actually does a decent job of synchronizing files, site configuration, certificates etc.

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I agree and wish that this question had answers. Web Farm Framework is still unstable and routinely takes down a node because it is "unhealthy". It's bad at managing memory, and if anything uses too much memory it will crash the web farm agent on worker nodes due to OutOfMemory indefinitely, even after resources have been released by the other process. –  jocull Jun 24 at 14:49

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How about rolling your own with PowerShell? I've built PowerShell frameworks around "legacy" MSI based installers for web sites since it has great support for running commands remotely and coordinating workflows between various processes. It can be painful to start, but PowerShell pretty much has full access to the OS and IIS configuration settings, and combined with standard monitoring system provides a great tool for automating and maintaining web deployments on multiple systems.

There are also commercial solutions like Octopus Deploy or RedGate's Deployment Manager and various configuration management systems (Chef, Puppet, Windows DSC) that can be used to automate system configuration.

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Yeah, we currently use Octopus Deploy to deploy our IIS apps. –  JohannesH Jul 20 at 12:00

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