https://ttlc.intuit.com/community/tax-credits-deductions/discussion/make-cobra-medical-insurance-payments-tax-deductible/01/569132#M73784 My employer used to pay my medical insurance premium payments pre tax. Now I switched to COBRA and make payments myself. I switched in Nov 2015. So for Nov and December, I'd like to make the premium payments tax deductible. Can I do that ? Wed, 05 Jun 2019 18:59:10 GMT LordDarkWarrior 2019-06-05T18:59:10Z https://ttlc.intuit.com/community/tax-credits-deductions/discussion/make-cobra-medical-insurance-payments-tax-deductible/01/569132#M73784 My employer used to pay my medical insurance premium payments pre tax. Now I switched to COBRA and make payments myself. I switched in Nov 2015. So for Nov and December, I'd like to make the premium payments tax deductible. Can I do that ? Wed, 05 Jun 2019 18:59:10 GMT https://ttlc.intuit.com/community/tax-credits-deductions/discussion/make-cobra-medical-insurance-payments-tax-deductible/01/569132#M73784 LordDarkWarrior 2019-06-05T18:59:10Z https://ttlc.intuit.com/community/tax-credits-deductions/discussion/yes-paying-medical-insurance-premiums-for-cobra-out-of-p/01/569141#M73786 <P>Yes, paying medical insurance premiums for COBRA out of pocket is deducible when&nbsp;itemizing on Schedule A. This is reported in <B>Federal Taxes, Deductions &amp; Credits, Other Tax Breaks, Medical Expenses</B>. See the FAQ below for more info.&nbsp;<A href="https://ttlc.intuit.com/replies/3301457" target="_blank">https://ttlc.intuit.com/replies/3301457</A></P> Wed, 05 Jun 2019 18:59:12 GMT https://ttlc.intuit.com/community/tax-credits-deductions/discussion/yes-paying-medical-insurance-premiums-for-cobra-out-of-p/01/569141#M73786 HollyP 2019-06-05T18:59:12Z