Sql Server Management Studio can't remember passwords When I connect to a database using ssms, I also have a checkbox labelled "Remember password". However, ssms will not remember the password. The next time I connect to the same server, I have to write it again.

What is the actual functionality of the "remember password" checkbox?
As said in the link from comment, It's a bug in SQL Server Management Studio

SQL Server 2012 Management Studio spuriously forgets password. and SQL Server Management studio solution explorer doesn't remember SQL authentication password

Some alternate solutions may work for you.