Error message: “the operating system is not configured for that operation”

Occasional Contributor

We have the error documented in this blog post below;


 This is happening more and more on our computer fleet as we upgrade staff to the latest C2R version of Office 365\2016. The blog post mentions that after following the steps (launching Outlook before Skype4B) the problem went away for them.


For us however, it does not.


I have submitted tickets to Microsoft through the Office 365 Admin portal but their solution is to "re-image the device". Ok sure, we can test that with a few to see if it helps, but we simply cannot re-image all 150 laptops that we have. That's ridiculous.


Our environment is;


Windows 10 Pro \ Windows 10 Enterprise (mostly 1703).

Office 365 (Click 2 Run install from the Office portal).

Skype for Business client (from the above install).


Is anyone else getting this error also? As it's starting to become more widespread, this is one of those errors that almost makes you start regretting your Office 365 migration...


Thanks in advance. All advice is appreciated. 

7 Replies

Can you give a bit more detail on what you are doing to the machine before this error occurs?

For example, the machine has a previous version of Office 2013 C2R, or Office 2013 MSI (Volume License) and you are trying to upgrade to Office 2016 C2R using [Manual Install/Group Policy/Script/Configuration Manager/Other] ?


I have not encountered this error before so it makes me think it has to do with the steps that are being performed on the machine to cause this to happen.


Also, just curious, does going into Control Panel and doing an "Online Repair" fix the problem (as a work-around?).


Is this problem happening on all 150 systems now or just the ones you are upgrading?

This is happening on devices that have brand new installs of the Office 2016 C2R from the office portal, done manually.


Doing an online repair doesn't fix the issue either.


It seems to be happening on systems that are the most up to date with Office updates.

Was there ever any previous version of MS Office on the machine? It sounds to me as if there is a lingering component from a previous install that was not uninstalled.

Prior to installing O365 C2R, all previous versions of C2R or MSI including Project and Visio and shared components need to be scrubbed from the machine.

There are a few automated scripts available in the community that can help scorch previous office installs.

Or is this a brand new machine that you are experiencing this behavior with? There has to be something on the machine causing this, otherwise all of us would be seeing what you are experiencing.


My device may have traces of older Office versions, but I know that my managers one does not. When he started we imaged it fresh, to put the 1709 update onto it. Now, 1 week later he's getting the same error I do.

Since the problem did not immediately appear on the manager's workstation, I would look in the event log around the time he/she first saw the error, perhaps something is getting installed on the machine that is causing this behavior to occur. That would make sense because a freshly imaged machine may not have all the apps the manager needs, then a week later they install an app and WHAM.. it causes this problem. My recommendation is to start again with a fresh image, then see if the problem occurs, watching the event logs for evidence of what is getting installed on the device.

I've since discovered that my managers device only had W10 build 1703.

I have updated mine to 1709 and the problem has gone away. We will update a few others experiencing this issue and see if it resolves this for them also.

Did you ever resolve this problem?  We're also seeing it on a number of machines, but not all.  We image all of our systems and then add additional apps as needed with SCCM.  I'm suspecting it's one of those additional apps which is causing the problem.