Oudie Updater will recognize an Oudie when it is connected to PC regardless if it is connected by USB or Active Sync. It will automatically detect whether something on your Oudie needs to be updated. If your Oudie is up to date then the Updater will quietly sit in the Windows Tray and will not do anything.

If there is something that needs your attention it will give you a message baloon at the bottom of the screen:

When you see this message - click on it. It will open a larger dialog where you can update your Oudie to the latest version with a few clicks: