I'm having a hard time figuring out why wireless wake-on-lan won't work. I'm playing music wireless from iTunes to my stereo through an Airport Express. 1) Should wake-on-lan work from the iPhone Remote app? If my iMac is not in sleep-mode, I can select music to play with Remote. However, if I have played music for say an hour the iMac is in sleep mode. The music still plays, but I can't use Remote anymore. I have to go upstairs to unsleep my iMac before everything works again. I have a late 2009 iMac. And I purchased the Airport Express last week, it has firmware 7.5.2 on it. I have followed the instructions from Apple from this page: http://support.apple.com/kb/HT3774 I have selected (checked) "Wake for network access" in System Preferences In system profiler I see "Wake On Wireless: Supported" 2) The strange thing is, when I use an utility like NetAwake, I can get my iMac out of sleep mode if it is only a few minutes or so in sleep mode. But if my iMac is sleeping longer, it does not work anymore.