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I enrolled in HDHP plan starting 2014 Nov 3rd. I also have an employer sponsored HSA plan, where my employer contributed $250 towards the 2014 limit in Jan 2015. Before this I never had an HSA account. So is it possible for me make the remaining contribution out of my pocket to meet the max. 2014 limit ( 3300 - 250 = 3050 )? I think this is possible at least based on what I understand from the IRS publication 969 and other answers. Do I need to contact my employer or I can directly talk to the HSA company to make these contributions?

Also is my understanding correct that if I lose my job in 2015, I can buy an personal HDHP plan off the market to ensure that I will not get penalized for the excess contribution (since I need to make sure that I have HSA compatible HDHP till Dec 2015)?

I file my taxes jointly with my spouse who does not have a HDHP coverage (also no FSA). Is my max. contribution limit $6550 or $3300? I think it is the latter as there are no other family members covered under my HDHP.

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Since you have self-only coverage on your HDHP, your annual contribution limit for tax year 2014 is $3300. This includes all money that was put into the HSA on your behalf, whether it actually came from you, before or after tax, or your employer.

Under the last month rule, since you had HDHP coverage on December 1, 2014 and still have coverage now, you are allowed the maximum limit for tax year 2014 ($3300). The caveat, as you mentioned, is that you need to maintain HDHP coverage until December 31, 2015. If you do not, then your 2014 limit becomes $275 (1/12 of $3300), and you'll have to pay tax plus a 10% penalty on the extra amount. (See this question for more details.) Yes, if you lose your job and are no longer in your HDHP plan, you can buy an HDHP plan individually or continue coverage with COBRA to maintain your HSA eligibility.

Assuming that you want to put in the maximum amount allowed in 2014, since your employer has already put $250 in your HSA, you can still contribute $3050 ($3300 - $250) for tax year 2014. You have until April 15, 2015 to do this. If I were you, for previous year contributions, I would eliminate the middle man and talk directly to the HSA company to handle these contributions. When you make contributions for a previous year, you need to explicitly tell the HSA provider which tax year the contributions are for, because they report all the contributions to the IRS, and you want them to get it right. You'll be making after tax contributions, which can then be deducted from your income when you do your 2014 taxes. (HSA contributions are handled on Form 8889.)

For 2015, if you decide to contribute to your HSA through your employer with payroll deduction, those contributions are before tax, and are not deducted on your tax return (because they weren't included in your income to begin with).

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