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My boss will be out of town and he wants all of his emails deleted after an out of office is sent. A quick test suggests that if I set an out of office and add a rule: Delete (don't accept message), the message being refused happens first so the out of office is never sent.

I could add a rule to have it filtered to a separate folder and then delete the folder at the end of his vacation but that would likely sync with his Outlook and he'd see the folder. This might still be the best solution, however I am hoping that I can the message deleted.

This is using Lotus Notes 9 and I have access to his Outlook or webmail client.

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If you filter them to a folder and then delete the folder, that won't delete the messages that were in the folder. They will still exist and be accessible through 'All Documents' view. If you want to get rid of the messages, you will have to select them in the folder and delete them, and then delete the folder. You could automate this by writing a simple agent to delete the filtered messages nightly.

Personally, unless he's worried about exceeding his mail storage quota, I would suggest to your boss that filtering them to a folder and keeping them, just in case, is a better strategy. He doesn't have to look at them unless it's absolutely necessary. And he doesn't have to tell anyone that he kept them. But if it is discovered after he returns that something important was sent, and the sender did not notice that he was away and neglected to keep a copy, this strategy will put your boss in the position of saving the day.

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