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I have a Sharepoint site with several custom lists, and lately some people started to use "List > Connect to Outlook" (from the List panel while viewing a List) in order to read and reply to discussions directly from Outlook.

While it's a very interesting feature, it became a nightmare after a few days. Several discussions have been deleted by those users, probably because they had removed the entries from their Outlook (probably assuming it would only clear the discussions locally, just like an email).

At least we were able to recover those important discussions from the site collection recycle bin, but I would prefer finding the root cause of this and then provide them with a solution to the problem.

Is it possible to block the deletion of list entries and comments from Outlook?

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It's based on permissions, so no unless you wanted to block users from doing so at the List level. That said, you can disable the feature entirely via Group Policy. You do need the Office Administrative Templates (2016 linked for reference, but there are templates for each version of Office). After adding those to the domain, you can then modify a GPO. The setting is under User Configuration -> Policies -> Administrative Templates -> Microsoft Outlook [2016] -> Miscellaneous -> Miscellaneous -> PST Settings. Enable the policy Prevent users from adding PSTs to Outlook profiles and/or prevent using SharePoint PSTs. Then select the option No PSTs can be added. Unfortunately this is an all or nothing approach, as this will prevent standard PSTs from also being created.

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