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 111 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.

23 answers

DavidYorkshire 91 Reputation points

2023-01-10T16:39:50.43+00:00

I've had this issue a couple of times - first a few months back on a fileserver, but as the configuration was fairly simple I just clean installed it,leaving the data drive intact, then set up the share permissions again afterwards. Since then I've upgraded several servers with no issues but had the same problem today, with a management VM which has a lot of stuff installed and I didn't want to have to clean install it. The suggestion above to turn off updates at the beginning of the installer worked - thanks!
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Anonymous

2023-06-13T13:05:59.2433333+00:00

Here we are in June and still having this problem. Where are you guys downloading the older ISOs?
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Reymond Jonathan 0 Reputation points

2025-08-21T06:29:15.61+00:00

tried an inplace upgrade from w2k16 -> wk22 on HyperV -> no problem
tried the same on Vmware with 12.3.5 tools -> upgrade failed
2nd try with the Vmware network card removed + SW_DVD9_Win_Server_STD_CORE_2022_2108.iso -> successful
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Problem with in-place upgrade from Windows Server 2019 to 2022

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