Hey, getting Windows to manually synchronize the secure clock (necessary for DRM transfers) can be a real bugger.
Sometimes, opening the device connection (sync tab) will result in this message, offering to synchronize the secure clock. If only those geniuses had placed an option to do so in the drop down menus, we’d be in business.
Often, you can synchronize the secure clock by formatting the device, by using the Clip’s built-in format command, then retransfer the DRM content.
Please note that formatting erases all content from teh device, and you’ll need to reload. So be sure to save a copy of your music first.
If you use the Rhapsody service, the Secure Clock can be manually synchronized. This clock is quite different from the familiar HH:MM:SS clocks we use every day; the secure clock is for the DRM system only.
To synchronize with the Rhapsody 4 client, a little trick is required.
Open R4 and plug in your Clip, in MTP mode. Now try this! Right click on the Clip, and Deauthorize, Format, and License will show up. Try again, but HOLD [ctrl] + [shift] while right clicking a second time. Behold! A new option: Reset Secure Clock.