Outlook 365 message "Windows search module disabled", Windows Server 2022, terminal server environment (Feb. 2024)

[German]I'm posting a problem here in the blog that was brought to my attention by a blog reader recently. The administrator in question is struggling with the fact that he keeps seeing the message "Windows search module deactivated" in Outlook 365. These are terminal server environments that run on Windows Server 2022. The question that arises: "Are others affected?".

A reader message

A blog reader sent me an email on February 27, 2024, in which he describes his configuration and the problem in more detail. Below are the boundary conditions:

• Windows Server 2022 is used, on which a terminal server environment is running.
• The users work with Microsoft 365 and therefore also with Outlook 365.

The combination initially raised question marks for me, because Terminal Server is somehow "Microsoft's unloved child". And then there was the issue that Office 365 apps were not officially supported under Windows Server 2022 for a long time. This has now been cleared up by Microsoft (see Windows Server 2022: Support for MS 365 Apps till October 2026).

Outlook error "Windows search module deactivated"

Now the reader (IT service provider for SMEs) has been facing an unpleasant problem for days and writes that "since the server updates of the last few days", two customers with a terminal server environment on Windows Server 2022 are now spontaneously running into problems. The customers are receiving a message in Outlook 365 that the Windows search module is deactivated.

The user is notified to contact the system administrator and without the "Windows search module", Outlook would no longer provide quick search results with the new functionality in the instant search. There is indeed a checkbox "Do not show this message again". But the reader wrote: "Unfortunately, checking this box does not work."

The reader narrows down the problem to the extent that, according to his observations, the message currently only seems to occur on Windows Server 2022 systems with Terminal Server. And here is a brief summary of the observations:

• At one customer, several users were affected at the same time. The IT service provider then activated the Windows Search service on the terminal server (TS) and the message disappeared for the affected employees.
• At the second customer, there has so far only been one response stating that the error had occurred. However, there is a terminal server farm there where it has not yet been decided whether it makes sense to reactivate the service on all terminal servers for this error, especially as the error has only occurred there once so far.

The reader wrote: "Unfortunately, I haven't found any public reports about this yet" and asked: "Maybe there is someone in the community who has noticed the same thing."

I did a quick internet search, the message that the "Windows search module" is disabled has been discussed in connection with Microsoft Outlook from time to time for years (see the old MS Answers thread here or the English MS Answers thread here as an example). Like the blog reader, I have not found any more recent reports from 2024 – and specifically on terminal server environments – in a hurry.

An administrator wrote in a comment within the German blog "On a terminal server, Windows Search must be installed separately via the server manager – it is not installed by default like on a Win10/11." Then the initial blog reader added the following explanation:

• Windows Search has been installed on all terminal servers from the outset, but was deactivated as it made sense due to previous problems.
• The popup warning appeared spontaneously after installing the February updates for two customers the following day, who have had exactly the same Server 2022/Office 365 combination for some time, so far without a pop-up.
• The window can be closed by ticking the box, but then it pops up again the next time the Outlook search is used. All you have to do is simply click on the search field; you do not have to start a search.
• The only way to make the window disappear permanently for employees is to activate the search service on the TS. However, this is not always desired.

The reader writes: "Maybe there are other colleagues with the same "problem"? The message is new and has not appeared before with the same configuration. I suspect a dependency on the latest updates from MS, but I can't narrow this down yet." Hence my question: Anyone else from the blog readership with the same observations?