Queued Items

Hold Power Button till Xbox shuts down. Turn it back on and once you are signed in, sign out and back in again. If none start downloading, disconnect Internet from Xbox. Reconnect Internet and try again. Other than that, wait 24 hours and see if they start
on their own.

Also, seeing alot of complaints of slow downloads so it may be an Xbox server issue but, I wouldn't say for sure.

Can you try queuing up items for download via xbox.com?

Hi,

The exact method is a little hazy, but as I understand it, you'll need to start one download, then add another to the queue. The second item (the one queued) can have the download location changed from within the Xbox 360 mini guide.

So, choose to download something and then add the actual content you want to download to the external drive to the Queue. Change the install location on queued item and then cancel the first first download. The content that was queued will now download to the external storage.

Ran into the same issue. Had to choose download this item first, THEN got the download all items option on the next screen. Also, may be stating the obvious here, but male sure there's more than one item queued for download.

Whenever this happens, select the option to "Download All Items". Once done, this will associate your new XBox as the primary console for your account, and all future items queued from the website will be sent this console.