We recently had a case where a role was stuck in this state. So on the portal, the deployment line said “Initializing” and the role says “Preparing Node” and it never moves past this. We cannot remote in using RDP or anything else to see what is happening with the deployment. The error looks like:
Turns out one problem that can cause this is if you are using Unicode file names. During the packaging and preparation of the files, we urlencode the names so that they can be stored in a compressed format. If the encoded file names become longer then 260 bytes, then the compression tools fail to unzip the package correctly and you will be left in a state like this when trying to deploy.
There are a couple of things you can do here to fix this problem.
Using either of these methods will allow you to deploy successfully to Azure.