Expected IRV recording isn't playing

ok so i’m a college intern working at my cousins company, i’m trying to set up our company’s phone system such that if anyone calls they get directed to an operator that will list out the option and such (just like how it would be if you were to call any other company’s help line). Unfortunately the voice recording doesn’t work if you are calling from an inside extention to a DID, it works if you call the extension or if u call from an outside line but not otherwise, i was wondering if there is any problem is or is it set up like this?