Hi came accorss this while looking for a fix for my own fault.
Just to let you know having multipul addresses is done in a few ways you can have different accoutns all opened at once (you will see down left hand side more than one mail box and need to go to each inbox to see there mail) or you can have multipull address set up to the same account. All emails will come into your standered inbox.
If what you have set up is different accounts then you will only activate out of office on your main account as technicaly all your doing is veiwing the other accounts not editing them.
If you have the second option (multipul addresses to one account) then i know why you only got back one response.
Out of office only replys to each person on the first email sent so if you sent from your hotmail accoutn the first time you woudl get an out of office response the second time you sent from that account to any of the other addresses the server will see you are already aware of the out of office and will not resend it. This provents too much trafic and is the default configuration on the server.
However with either option some form of out of office should have gone out at some stage and your notes on what you did to set it up are 100% correct! your IT team there should be aware its correct and inform your boss this was a system fault not yours!
There is always the possibility that the sender has it set up to bar these responses (as they can be classed by some filters as spam) and most companys these days ban the received receipt emails so this may also not work for you.
Think this is a fault for your IT team and you should not be punished for it.