Hi @Labsy
I would firstly suggest you upgrade your Exchange 2010 server to a later version, for example: Exchange 2016, since Exchange Server 2010 reached its end of support on October 13, 2020.
Details: Exchange 2010 end of support roadmap
And according to your description above, the issue occured on OWA as well, so the issue may be related to server side, we could follow the steps here to rebuild the search index.
1.Launch Exchange Management Shell as administrator (right click run as administrator)
2.type get-mailboxdatabase to get the names of the databases. Copy the name of the database you’d like to rebuild.
3.browse to the scripts directory by typing the following:
cd\
cd “program files\microsoft\exchange server\v14\scripts”
4.Enter the following command to rebuild:
ResetSearchIndex.ps1 “Mailbox Database 1”
Note: specify your desired database name instead of “Mailbox Database 1”
Another document introduces about Troubleshooting Exchange 2010 Search for your reference as well
In addition, recently a known issue about outlook search is related to Windows update KB5008212. After you install update KB5008212, recent emails may not appear in search results.
And the TEMPORARY WORKAROUND is disabling Windows Desktop Search which will cause Outlook to use it's built-in search.
- In Windows, right-click Start, and then select Run. In the Open: box type regedit, and then click OK. This will open the registry editor.
- Find this subkey in the registry and then click it: HKEY_LOCAL_MACHINE\SOFTWARE\Policies\Microsoft\Windows
- Click Edit > New > Key and name the new key Windows Search.
- Select the new Windows Search key.
- Click Edit > New > DWORD Value.
- Type PreventIndexingOutlook for the name of the DWORD, and then press Enter.
- Right-click PreventIndexingOutlook, and then click Modify.
- In the Value data box, type 1 to enable the registry entry, and then click OK.
- Exit Registry Editor, and then restart Outlook.
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