I've been having strange errors in the behaviour of the scheduled publishing for various versions of Umbraco when deployed on Azure on our UAT and production environments. The following errors in the logs constantly appear.

The site is hosted on an https binding in IIS 8.

The currently deployed version of Umbraco for the site is 7.1.9 where the logs occur and the scheduled publishing does not complete.

After attempting to deploy a virgin 7.2.1 instance to the same environment the same errors appear however the publishing appears to actually work as expected despite the errors.

I've reviewed some other similar topics on the matter and attempted the fixes described to no avail. I'm wondering if there's something else I am missing here?

http://our.umbraco.org/forum/core/general/56407-Worrying-errors-in-the-logs-over-last-couple-of-days-from-UmbracoWebSchedulingScheduledPublishing-?p=0

http://issues.umbraco.org/issue/U4-5842

http://issues.umbraco.org/issue/U4-5379

The only thought I had considering the explanation given by Sebastiaan was after the OriginalRequestUrl fix had been implemented I'm seeing in the logs:

2015-02-04 10:31:32,073 [17] INFO  Umbraco.Web.UmbracoModule - [Thread 10] Setting OriginalRequestUrl: test.[company].com:443/umbraco

Now the site being hosted on https would not bind any requested made to http://test.[company].com:443/umbraco which I'm guessing would cause the timeout? Is there a setting I'm missing to enable this?

I have set umbracoUseSSL to true but this has not helped.

Thanks in advance.

2015-02-04 12:00:45,647 [20] ERROR Umbraco.Web.Scheduling.KeepAlive - [Thread 108] Error in ping
System.Net.WebException: The operation has timed out
   at System.Net.WebClient.DownloadDataInternal(Uri address, WebRequest& request)
   at System.Net.WebClient.DownloadString(Uri address)
   at Umbraco.Web.Scheduling.KeepAlive.Start(ApplicationContext appContext,   IUmbracoSettingsSection settings)
 2015-02-04 12:01:17,644 [73] INFO  umbraco.BusinessLogic.Log - [Thread 125] Log scrubbed.  Removed all items older than 2014-12-06 12:01:17
2015-02-04 12:01:17,644 [20] INFO  umbraco.BusinessLogic.Log - [Thread 108] Log scrubbed.  Removed all items older than 2014-12-06 12:01:17
2015-02-04 12:01:25,624 [20] ERROR Umbraco.Web.Scheduling.ScheduledPublishing - [Thread 14] An error occurred with the scheduled publishing
System.Net.WebException: The operation has timed out
   at System.Net.WebClient.UploadDataInternal(Uri address, String method, Byte[] data, WebRequest& request)
   at System.Net.WebClient.UploadString(Uri address, String method, String data)
   at Umbraco.Web.Scheduling.ScheduledPublishing.Run()