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I have had the same Family HSA for years 2011, 2012, 2013 and have met all IRS testing and eligibility for those years. I have the same Family HSA for 2014, but will be switching jobs where my employer will offer only an FSA. I am over 55 and had planned on contributing the max $7550 for 2014: $262.50 x 24 payrolls (Jan 15 - Dec 31, 2014) + $250 employer bonus + $1000 my contribution (both in Jan 2014) = $7550 My old job will terminate Aug 3, 2014, with 2 more paychecks being paid to me thru Aug 31. I will have total of $5450 thru August 31 contributed to my a/c via payroll deduction and other contrb noted above. I will be enrolled in the FSA (not sure what type) effective Aug 4, 2014. I have medical bills I would like to pay from my HSA which I will have incurred prior to Aug 4, and noting other posts on this site, I can still keep my HSA with the remaining balance and pay those bills, but I cannot add to my HSA after Aug 3. Can I contribute the additional $2100 to my HSA from my own funds prior to Aug 3 while I am still with my old employer, and not be penalized for over funding the HSA because of the FSA signup on Aug 4? If not, how do I calculate and what is the maximum amount I am allowed to contribute into my HSA for 2014, taking into consideration this job change and FSA starting in August? I have not been able to find an answer to this particular question, and it seems like a common one! Thanks for info and help!