So, I understand that although under COBRA, since I will still be in a HDHP, I am eligible to make HSA contribution (up to the allowed yearly maximum). if this is correct?
as long as the COBRA insurance is a high-deductible plan you are correct.
will my HSA contributions while on COBRA be tax-exempt? what do you mean? you get a tax deduction for the contributions to an HSA plan (form 8889). you can not deduct any expenses paid through the HSA. so only the portion, if any, of COBRA premiums that are not paid through the HSA would be an eligible medical expense deductible on schedule A even if self-employed. When you're self-employed, the Internal Revenue Service does allow you to write off qualifying medical insurance premiums as self-employed health insurance because to qualify, the insurance plan must be created under your trade or business name. COBRA coverage continues your existing coverage under your previous employer's plan. Therefore, because you didn't create the policy under your self-employed business name, you can't include the COBRA insurance premiums you pay as part of the self-employed medical insurance deduction.
If so, do I claim the tax-exemption when I file my tax return next year? Will this be possible, even if I do not itemize deductions? the deduction for HSA goes on schedule 1 (2020 who knows what form in 2021) and is a deduction to arrive at adjusted gross income which means you do not have to itemize to get the benefit but you do need to have income in excess of the standard deduction. to get a tax benefit.
