Strange updating problem

I have an odd problem with a small application that is written in VB.NET, reading from and updating an SQL Express 2012 server.  The app pulls a datareader from a view and then loops through it and sends each record to an offsite db via an http post.  It then goes and marks the record sent using an update query to set a sync bit value in the main key table.  It then goes to the next record in the reader and repeats the process (or that was the idea). 
What happens when it runs is that the update operation fails with a “Connection timeout or server instance not found “ erro ...