Strange intermittent SQL connection error, fixes on reboot, comes back after 3-5 days (ASP.NET)

Question

For some reason every 3-5 days our web app loses the ability to open a connection to the db with the following error, the strange thing is that all we have to do is reboot t

Answer 1

Have you tried collecting basic information with perfmon and profiler (trace) to see how many connections are made, memory stats and other interesting things?