I
don't want just one email response per time the Out of Office AutoResponder is turned on. The boss is going to be gone for over two weeks and if someone sends him an email today and then another one again next Monday, that person won't receive another response and may not remember that the boss is out of the office (and won't get a response).
I found a way to use a
rule to auto respond which included a "Don't reply to Auto Reply emails (negating the infinite loop), but it too appears to have a setting (not adjustable) which prevents multiple responses to the same person - I don't know if that limit is once per day or once per startup.
Also, it is a local rule, so his machine would need to stay on with Outlook running (not a big deal).