Does Health Insurance Affect Your Tax Return? 
First , let me say I am not an accountant or tax expert at all . This questions would be best answered by a Certified Public Account or other tax pro . I can only speak to my personal situation . For years we did n't have a group plan through my company and I had individual/familycoverage that I paid for out of pocket . I also have family members who have some health issues that included specialists , a lot of RX drugs , etc. . Simply due to the cost of the health coverage , we had to go with a high deductible health plan as well . So , over the course of a year we would have our health premiums , high deductibles , plus a bunch of specialist costs that were not even covered by our insurance . This generated a ton of dollars that came out of my pocket personally . There is a threshold for medical expences -LRB- I do n't remember what it is -RRB- where anything over an above that figure is deductible on your tax return . I have been well over that figure every year for the last 5 or 6 , so I have been able to deduct a good amount of my out of pocket expence . This is just my personal situation and again , I am not a tax professional of any sort . All this was done on the advice of my personal accountant . I would highly recomend you contact a tax professional and discuss your individual situation with them . 