Generate a debug log (step 4b) capturing the connection of the Walkman and subsequent failure to delete file (which only works with AutoSync!) and send it to support: http://www.mediamonkey.com/forum/viewtopic.php?f=7&t=69

I have used a couple of Walkmans with MM - currently a NWZ-S765. They both work well with MM, but I have had problems with AutoSync with both devices and MM4 (including the latest 4.0.5) in that the synchronization process does not delete files not on the device, so the synchronization does not complete. You can get ground this by reformatting the Walkman and then running the sync, but this is a bit of a long-winded process. The synchronization issue might be related to me installation, and apart from that the Walkman and MM go together well, and the Walkman is an excellent MP3 player.

You may want to upgrade to 4.0.5 to see if the improvements also work on your device.

Hi,
About a month ago, I bought an itty bitty mp3 player called "Ice Latte" (here's the link).
http://www.google.com/products/catalog?hl=en&safe=off&rlz=1C1CHFX_enUS457US457&bav=on.2,or.r_gc.r_pw.r_cp.r_qf.,cf.osb&biw=1229&bih=616&q=ice+mp3+player&um=1&ie=UTF-8&tbm=shop&cid=5391981056624721068&sa=X&ei=-XTPT8LWD-GC6AHBocCrDA&ved=0CIUBEPMCMAQ

It sucks pretty badly and isn't compatible with MediaMonkey. I.E. the playlists I make in MediaMonkey just com up as .mu3p or .mpu3 or something and won't play.

What I'm asking is, if I order this:
http://www.amazon.com/Sony-NWZE465BLK-Walkman-MP3-player/dp/B005EQS9KS/ref=sr_1_1?s=electronics&ie=UTF8&qid=1338995657&sr=1-1

Will it be compatible with MediaMonkey? Will it accept my MediaMonkey playlists and play them as its own?

Thanks. =) Also, if anyone has had any positive or negative experiences with the Sony Walkman I'm interested in, please let me know.