Here's something else to throw in your retirement notes. During the open enrollment period the year before you retire take at look at signing up for the Health Care Savings deduction if you need anything done in the next year. I stumbled across this by accident. My wife needed some dental work we had scheduled for January so I had them take money out. They divide the repayments into 24 equal payroll deductions. My last paycheck will be 30 September so I get 6 payments for "free". Thought this might be a mistake but the folks at Wage Works confirmed it.