Ok this issue has been plaguing me for months and I just can't resolve it. I have an iMac (early 2008, supports wake on wireless) with Snow Leopard basically providing all of our services like iTunes, files etc. After the blasted thing falls asleep, when I try to connect to it in Finder with my macbook it'll say "connection failed". If I go wake it up, everything will work fine. I have an Airport Extreme (dual band). It'll show the machine available in finder while it's sleeping, I just can't wake it up. The option "Wake for Network Access" is selected on the Imac. Not sure why it won't wake up. At first the iMac was connected via airport wireless. I tried connecting the ethernet port to a base station and disabling wireless instead but the same issue exists. Thanks in advance for any help..