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I know this is almost a duplicate of : The error "Login failed for user 'NT AUTHORITY\IUSR'" in ASP.NET and SQL Server 2008 and Login failed for user 'username' - System.Data.SqlClient.SqlException with LINQ in external project / class library but some things don't add up compared to other appliations on my server and I am not sure why. Boxes being used: Web Box SQL Box SQL Test Box My Application: I have an ASP.NET Web Application, which references a class library that uses LINQ-to-SQL. Connection string set up properly in the class library. As per Login failed for user 'username' - System.Data.SqlClient.SqlException with LINQ in external project / class library I also added this connection string to the Web Application. The connection string uses SQL credentials as so (in both web app and class library): <add name="Namespace.My.MySettings.ConnectionStringProduction" connectionString="Data Source=(SQL Test Box);Initial Catalog=(db name);Persist Security Info=True;User ID=ID;Password=Password" providerName="System.Data.SqlClient" /> This connection confirmed as working via adding it to Server Explorer. This is the connection string my .dbml file is using. The problem: I get the following error: System.Data.SqlClient.SqlException: Login failed for user 'DOMAIN\MACHINENAME$'. Now referencing this <a href="https://stackoverflow.com/q

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