So this issue is NOT one of having too many connection strings or connection strings not being disposed of properly. ASP.NET Sql Server stored session has been working great for months with decent traffic on the website, now I am getting many Unable to connect to SQL Server session database - The wait operation timed out exceptions. There is plenty of memory available for the database, the database has plenty of memory allocated. There is just a few users on the website when it is throwing errors.
I have two blade servers sitting right next to each other and very low traffic to the website so I shouldn't need to increase the connection timeout from the default 15 seconds.
I am using Windows Authentication and I can connect via SSMS and query my ASPSession database that is being used as the persistence layer for ASP.SESSION no problem.
I just have no were to go on this error currently.