Here's what I'm running. I have MM 4.06.1501 and I have an iPod touch Gen 4 which I just upgraded to the current software, 5.1.1. Prior to upgrading the iPod everything worked fine with the Monkey and I was able to put music on the iPod by 'highlighting' the songs and then use the "Send To" tab.
When I found that MM 4.06 would play nicely with IOS 5, I made the jump and upgraded. Since then, this is what I have been experiencing. If I highlight an album and hit 'send to' I get the green status bar at the bottom for a bit, as if the songs are converting, and then MM shuts down. Usually just one song will then appear on my iPod, but it is in grey and will not play. I get the same results when I select only one song and try to send it to my iPod, it is grey and will not play.
Any help would be greatly appreciated, thanks,