It may be only that the MyDrive application isn't automatically coming up if the browser is already running, or that it isn't automatically initiating a browser launch. With your 2050 connected, and using the PC (it's what I'm most familiar with), assure that the 'MyDrive Connect' (or if its been ages since you updated the app, the 'My TomTom' - I will hereafter assume you have the newer app and I will use the MyDrive Connect name) systray icon is present. If so, the computer has recognized the device, but the application has not auto-launched a browser page. If your browser isn't running, launch it manually. Then right click the icon and select the top item 'MyDrive'.
If the systray icon is NOT present, then the MyDrive Connect application is not running. Locate it on your PC. It is called MyDriveConnect.exe, and should be in an application folder called MyDrive Connect. Double click on that to manually execute it. Watch to assure that the systray icon appears and continue from there.
If the systray icon already appears, but it does not seem that the device is recognized (selecting MyDrive Connect from the systray icon brings up a browser screen indicating that the device is not connected), then we have a somewhat larger problem that I will address -- but not unless we find that's the ditch you're in.