You can disregard answering my first question. I coded it and it works without background session. So thank you for pointing that out. But if you can take a look at my other two questions - .earliestBeginDate & Rescheduling - it would be appreciated.

Kevin Elliott, This is very helpful, thank you. I have found that during testing using Background Sessions using a NSURLSessionUploadTask rather than NSURLSessionDownloadTask for a file upload increased the speed of the file upload significantly. I also found that following the pace of the file upload can be deceiving as the first 3-5MB can take a few minutes, but then each subsequent part uploads much faster. So if uploadTaskWithRequest: fromFile: will work on an NSURLSession executed through the BGProcessingTask Framework I have a great solution for my problem. That is what I am testing now.. Your insight should help.