Came through this interesting issue a while ago, thought it’s worth writing.
A user reported that he is not able to use his OOO, because it’s grayed out.
While checking some features found out the root cause, to enable the OOO feature again, follow the below steps:
1. Go to Tools menu -->Options
2. In the pop-up window select the “Other” tab.
3. Click the “Advanced options” button at the top part of the window.
4. In the pop-up window click on the “Add-in manager” button.
5. A small window with various options opens, in that, click on the install button and select OUTEX.ECF and say OK also make sure that the "Exchange Extensions property Pages" option is selected.
6. Exit all the window by clicking OK.
7. Re-open Outlook and use the OOO feature.
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