PC Reset from Cloud - how to debug

Is there a way to debug PC reset using Cloud option? It seems that I have not encountered any single machine (yet) that would not be complaining about inability to download files from the Cloud making this option useless.

Are there some prerequisites? Eg if the base OS is 3 years old and was never updated can it still download the "latest" image? Are there some logs (I found only something like CloudRec.log but nothing helpful inside)? WinRE itself can work on network as I have seen that the process is downloading two CAB files from http://tlu.dl.delivery.mp.microsoft.com/filestreamingservice/... so something else then "downloading" is the problem.