I can't seem to figure out how to edit my question so I will respond to it.
I have some more details that I would like to add.
I have attempted to set the -timeout and -sendtimeout args to 60 and 120 seconds and it just spins for the specified amount of time and then closes with the error. By setting the -timeout to 1 second I can make most of the uploads fail, so I know that it is affecting the request. The files that upload without a problem are on the order of 30 KB where as the file that has never succeeded is on the order of 740 KB.
