OS upgrade from 2008R2 to 2012R2 -- Issues and solutions.

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With the forced expiration of 2008R2 by Microsoft, an upgrade to at least 2012R2 for your OutSystems servers is needed, and if you are not already on Server 2016 so that you can use OutSystems V11, you might find this helpful. 

Note that 2016 is a minimum requirement for V11, and V10 support Ends soon. So if you are upgrading, it's in your best interest to target a landing point of 2016 at a minimum.

Note also, we are using the .NET platform version. As such, I can only speak to that and our experiences therefore.

First, an in-place upgrade of the OS is possible, it is just a bit more involved than just running the OS upgrade and moving on. 

.NET will stop functioning, the OutSystems Platform will not be functional, and you will likely see some very odd errors from the Server.

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We found that, despite using an image that was supposedly fully patched, once installed, there are a great number of additional patches that you will need to apply. In our case that exceeded 180, with associated periodic reboots and knock-on patches required as prerequisites for the patches.

These patches are necessary for .NET to run. Even with .NET installed already, there are requirements and prerequisites for .NET on 2012R2 and 2016, that just won't bake into an image and have to be addressed post-upgrade. 

Once those are applied, the most current version of .NET can be installed to ensure full and proper function, and the last steps to get the OutSystems platform running again can be completed.

After the OS upgrade, patching, and .NET install, you will find that OutSystems is still not working. The fix for this is perhaps the simplest and quickest part of the process.

Open Configuration tool on all upgraded servers. Go to File > Apply and Exit , and do not do the Service Center install. 

Once  you have done that, check Service Center and restart any services, such as SMS or Scheduler, that are not responding. These will be those with the Red X in Environmental Health. After one, or two, restarts; you should be green check-marks across the board and everything running without issue.

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I hope our pain can help someone else, without having to do the alternative of building new servers, with fresh installs, and having to address all the back-end updates and changes to DNS, etc... 

Always make sure your Certificates in IIS are up to date as well.

Thank you very much Damon, for your sharing with community!