If you are performing a deployment and it is not working or working only after some effort.  One feature that might help you find the reason why is the deployment log available using KUDU.

You can access your deployment details by entering https://standard.scm.azurewebsites.net (where standard is the site name of your Windows Azure Web Site).  Using your Deployment credentials to login, you can click on the Deployments link, as shown in Figure 1, to download a JSON file containing your deployment logs.  If the issue is happening on the Windows Azure Web Site side, then the error is likely logged here which might lead you to a solution.  If there is no logged error, then the issue may be happening before the request reaches the Windows Azure platform.  In this case you want to focus you effort on the deployment platform.

Figure 1, Viewing Windows Azure Web Site deployment logs using Kudu