I don't think there is an issue with the commands I'm executing as much as how I'm executing them. I need to switch to another user to run some of these commands as the permission obviously is lacking.

I login via 'sa' (owner of 'testdb') but in context of SSMS (2008 R2) New Query window, I don't think I'm executing under 'sa'. How can I switch to 'sa' in this environment?

USE master

GO

CREATE MASTER KEY ENCRYPTION

BY PASSWORD = 'Password' -- just imagine the password passes the criteria for now

GO

OPEN MASTER KEY DECRYPTION

BY PASSWORD = 'Password'

GO

CREATE CERTIFICATE MyCert

WITH SUBJECT = 'My Cert'

GO

USE testdb

GO

CREATE SYMMETRIC KEY MYTableKey

WITH ALGORITHM = AES_256

ENCRYPTION BY CERTIFICATE MyCert

GO