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I need to perform an in-place upgrade of a remotely located Windows 2016 server to 2022 (or 2019). My only access to it is via Remote Desktop connection. Knowing that the upgrade process may require restarts, will I be able to re-connect my remote desktop session to continue with the upgrade process?

Obviously I need to know before attempting. I don't want to get into a situation where I can no longer connect to the server after a restart and have to get someone on site to finish it up.

ChazJ
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    Without a real remote *console* capability, you are on a real mission to shoot yourself in the foot. Leaving aside the whole problem that in-place upgrade is a bad idea anyway. Without any idea of the infrastructure, it's hard to make suggestions. If it's a physical computer in a branch office cupboard, get someone to buy replacement hardware - with remote management like DRAC/iLO this time - install the new OS, preload the data/app/whatever, get someone to pay to install the new box in the remote location and finalise data migration. – LeeM Mar 02 '23 at 06:46
  • Thank you for your comments. Believe me, I wish I could do it the right/safe way, but it is just not possible. However, in order to preserve my foot, I will at least make sure the gun is not loaded. :-) – ChazJ Mar 02 '23 at 19:38
  • All I can really advise now is to make sure any paperwork outlines the risk that this could a) corrupt the OS or application, or b) make the system unserviceable remotely - and ensure that someone in change control or management has reviewed and acknowledged those risks IN WRITING. It will *likely* work in terms of the OS upgrade, at least, and remain connected. But the risk is not nothing. (To be really frank, I'd start looking for a better job, with better resources and risk-management (I get it, beggars can't be choosers, but no harm looking :-) )) – LeeM Mar 02 '23 at 23:38

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If everything goes smooth, you will not loose RDP access. However, there is simply no 100% way to know this for sure in advance. There are countless scenarios how in-place upgrade can fail, so you definitely need to prepare a recovery plan in case remote upgrade goes wrong.

Anyway, general Microsoft recommendations can be found here: https://learn.microsoft.com/en-us/windows-server/get-started/perform-in-place-upgrade

J-M
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  • Thank you for your reply. I was more concerned as to whether the RDP settings were reset, changed or in any way touched during the upgrade. Obviously, failures, errors and such is a whole nuther ball game. Much appreciated... – ChazJ Mar 02 '23 at 19:28
  • RDP settings should stay, unless stated otherwise in upgrade documentation – J-M Mar 02 '23 at 20:00