So my company has a Windows Server with SQL Server on it that we use as a development server (our production server is hosted by an ISP). For some reason the development server started doing this thing where it never connects the first time, but connects fine the second time. This is when attempting to connect from the web app, or from management studio running on a remote machine on the local network. This doesn't seem to be an issue when connecting using management studio on the host server. Seems to be a network issue, but I've checked that the SQL Browser service is running and that the firewall is configured with ports 1433 TCP and 1434 UDP. Has anyone else experienced this? Any suggestions on how to fix it?