Could someone give me a 30K foot overview of the differences and relationships of a server login vs. a database login?
A Server Login is for authentication. A Database User is for authorization.
In the very simplest terms, a server login allows you to connect to the SQL Server database server. It's an outer shell for authenticating credentials.
The database user, on the other hand, does not have proper credentials of its own and relies on the server login for authentication. The database user's is used directly for authorization, allowing rights to be granted to database objects such as procs, tables, views.
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