Problem with in-place upgrade from Windows Server 2019 to 2022

TomaszW-0873 156

I have an issue when I try to do an in-place upgrade from Windows Server 2019 to Windows Server 2022. Installation itself starts, run okay but after restarting, system reverts to older version of Windows and I got the following errors:

0x800F081E-0x2003
The installation failed in the SAFE_OS phase with an error during INSTALL_UPDATES operation

Brian Hoyt 106 Reputation points

2023-03-16T16:10:12.6666667+00:00

The final answer for me was an updated ISO. I was told by a MSFT person that this was a bug fixed in November update. I got the latest ISO (Feb 2023 at the time) and was able to do in place upgrade on all my remaining servers.
Robert Sandri (rsandri) 5 Reputation points

2023-03-20T01:39:34.63+00:00

The Feb 2023 ISO will not work if you have applied VMware Tools 12.2.0 first. A Windows Server 2019 running VMware Tools 12.1.5 (and never previously upgraded to VMware Tools 12.2.0) will upgrade using the Feb 2023 ISO. If the Windows Server 2019 guest has been upgraded to the 12.2.0 VMware Tools, you will not be able to upgrade 2019 to 2022 for the time being.
DavidYorkshire 91 Reputation points

2023-03-20T08:27:43.78+00:00

Presumably you could uninstall the VMWare tools, do the upgrade then reinstall the tools?
Robert Sandri (rsandri) 5 Reputation points

2023-03-20T12:53:57.1166667+00:00

Removing or downgrading the VMware Tools has no effect. I did have success by using the Windows Server 2022 initial ISO released from Microsoft. Others have reported the same but using an ISO from 2021. I have not tested the latter.
Robert Sandri (rsandri) 5 Reputation points

2023-03-22T12:47:27.6833333+00:00

Solution: If you have already installed VMware Tools 12.2.0, you must use an older Windows 2022 ISO to perform an upgrade. I can confirm that the initial Windows Server 2022 release ISO works for the upgrade. Others have reported success with year 2021 ISO releases.
Chris Findley 0 Reputation points

2023-04-17T19:59:24.87+00:00

Experience date: April 2023, running VMware Tools version 12.1.0, Server 2019 with 23-04 Windows updates.

Using SW_DVD9_Win_Server_STD_CORE_2022_2108.11_64Bit_English_DC_STD_MLF_X23-17134.ISO failed with and without disabled update check.

Using SW_DVD9_Win_Server_STD_CORE_2022_2108.19_64Bit_English_DC_STD_MLF_X23-40586.ISO succeeded but only with disabled update check.

The subsequent check for Windows updates found 23-04 Cumulative and 22-08 Security for 21H2.
Robert Sandri (rsandri) 5 Reputation points

2023-06-13T13:12:29.76+00:00

I can confirm that the May 2023 version of the Windows Server 2022 ISO works for upgrades regardless of the situations outlined above,
Anonymous

2023-12-05T01:34:09.34+00:00

Hi Robert Sandri, Can you please post the May 2023 version of the Windows Server 2022 ISO full file name with prefix number part of it? e.g. SW_DVD9_Win_Server_STD_CORE_2022_2108.23_64BitEnglish_DC_STD_MLFX23-50413.ISO

As i am facing the issue with "The installation failed in the SAFE_OS phase" but it does not say : "INSTALL_UPDATES operation" for me but fails with: The installation failed in the SAFE_OS phase

I am trying to upgrade from Windows Server 2016 Standard(Desktop) to Windows Server 2022 (Desktop)
My VM is running on VMware Tools version is on: version:12384 as my ESXi hosts are running on ESXi version 8
Massimo Cracchiolo 0 Reputation points

2025-05-01T21:00:44.8233333+00:00

I was having the same problem with the Feb 2023 ISO. I happened to check and saw that there is a March 2025 ISO. I used the March 2025 ISO and was able to upgrade successfully without issue.

22 answers

RedVision81 31 Reputation points

2022-10-26T11:31:10.683+00:00
after spending days and a lot of try and error, in our Environment (VMware) the following method was finally successful
Our VMs are all equiped with VMware Paravirtual Controller and vmnext3 Network Controller.

When using VMware Tools 12.0.5 or later, you need to downgrade the Paravirtual Controller Driver below 1.3.25.0 (as suggested in Vmware KB https://kb.vmware.com/s/article/89290)

usual downgrade/installing older driver vom cd/iso via device manager is enough, no need to delete/remove drivers via command line - reboot the machine

upload Server 2022 August 2021 iso to vmware content library (current iso 2108.13 is running into a blue screen)

login with local administrator !! not domain administrator

mount Server2022 Iso to VM and run the upgrade

don't use the download updates, driver and optional feature function !! use "not right now"

lean back and cross your fingers ;)
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1 person found this answer helpful.
Michel Zehnder 21 Reputation points

2022-10-26T11:49:39.773+00:00

Holy smokes. An actual VMware KB article! Nice one. Will try this soon(ish) :)
Thanks for letting us know!
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Brian Hoyt 106 Reputation points

2023-03-16T16:09:46.02+00:00

The final answer for me was an updated ISO. I was told by a MSFT person that this was a bug fixed in November update. I got the latest ISO (Feb 2023 at the time) and was able to do in place upgrade on all my remaining servers.
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1 person found this answer helpful.
Alec Garcia 46 Reputation points

2023-03-16T16:16:21.4566667+00:00

About time they make an update that actaully fixes something!!!.....

Stanley Noel 1 Reputation point

2024-03-07T12:06:14.67+00:00

I used the SW_DVD9_Win_Server_STD_CORE_2022_2108.30_64Bit_English_DC_STD_MLF_X23-69130.iso on a VMware Tools v12.0 virtual machine and still fails. May have to look at a migration approach to new servers.
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RedVision81 31 Reputation points

2023-03-22T08:15:47.8033333+00:00

Inplace Update with current Server2022 Iso (SW_DVD9_Win_Server_STD_CORE_2022_2108.18_64Bit_English_DC_STD_MLF_X23-37922) and Vmware Tools 12.1.5 worked without any issues.
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Anonymous

2021-09-18T19:23:43.263+00:00

An in-place upgrade can be problematic and is never recommended. Better option is a clean install, patch fully, migrate roles over. You can check the logs for additional details.
https://learn.microsoft.com/en-us/troubleshoot/windows-client/deployment/windows-setup-log-file-locations

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TomaszW-0873 156 Reputation points

2021-09-18T21:44:34.04+00:00

It is a on-prem machine, so it will be difficult, but I will look in the logs.

Anonymous

2021-09-18T21:48:07.913+00:00

Sounds good, you're welcome; a simpler solution may be to clean install, patch fully, migrate roles over and move on.

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Anonymous

2021-09-19T13:17:30.083+00:00

Just checking if there's any progress or updates?

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TomaszW-0873 156 Reputation points

2021-09-19T13:29:39.093+00:00

I will go for separating roles to other machines and clean install

Anonymous

2021-09-19T13:32:16.377+00:00

Sounds like a good move.

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Anonymous

2021-09-20T14:19:16.173+00:00

Just checking if there's any progress or updates?

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TomaszW-0873 156 Reputation points

2021-09-20T14:24:07.08+00:00

I should be done by the end of the week, as I am in the progress of migratiobn. If I have any further issues, I will write them down.

Anonymous

2021-09-20T14:25:43.133+00:00

Glad to hear of progress.

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MaximillianC 101 Reputation points

2022-05-14T21:56:29.31+00:00

While your warning is technically "valid", in response to the question asked, it's unhelpful. When someone explains they're having trouble doing a Windows upgrade (which Microsoft and Windows do allow admins to do, for good reason), "you shouldn't be doing that" just comes across as dismissive, especially before asking why they're doing an upgrade instead of a fresh install. I have been upgrading my Windows OSes my entire life, and, fortunately, aside from some small snags here and there, my upgrades have saved me countless hours of time. Like many people, time is something I never have enough of, so I value mine greatly. For the average configuration, despite the warnings about upgrading, I've found that Microsoft actually tends to do a pretty good job of making Windows upgrades work very well, and that seems to have gotten better with every release. In fact, I'm pretty sure (try not to gasp) that I upgraded my main PC all the way from Windows 95 to Windows 10 (even moving it to different hardware), and have several servers that have gone through 4 or 5 Windows Server version upgrades, and continue to work beautifully. Since an upgrade takes FAR less time than doing a fresh OS install, and reinstalling and reconfiguring every single component and app on that machine, those of us who don't have hours of time to do full re-installs on our workstations and/or servers have really good reasons to go the upgrade route, instead.

Roy Charman 16 Reputation points

2022-08-19T12:14:54.92+00:00

How unhelpful.
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Docs 15,761 Reputation points

2021-09-19T01:37:40.52+00:00

List any of these installed non-Microsoft software:
a) antivirus
b) firewall
c) drive encryption

Run setupdaig > post a share link into this thread

https://learn.microsoft.com/en-us/windows/deployment/upgrade/setupdiag

Post commands with results for these administrative command prompt commands:

sfc /scannow
dism /online /cleanup-image /restorehealth
findstr /c:"[SR]" %windir%\logs\cbs\cbs.log >%userprofile%\desktopsfcdetails.txt
findstr /c:"conx" c:\$windows.~bt\sources\panther\setupact.log >"%userprofile%\desktop\setupactdetails.txt"
copy %windir%\logs\cbs\cbs.log "%userprofile%\desktop\cbs.txt"

Find the new text files on the desktop and post share links into this thread.

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Problem with in-place upgrade from Windows Server 2019 to 2022

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