If I apply for the extra help from Social Security and am approved, will I automatically be enrolled in a Medicare prescription drug plan?

Only if you do not enroll on your own.  If you do not enroll on your own, the Centers for Medicare & Medicaid Services will send you a letter in May 2006 that will tell you which plan you have been enrolled in and how to change plans.  However, you could lose months of benefits and you may not get the plan that is best for you if you wait to be automatically enrolled.