You do not enter a health insurance payment for yourself as a business expense. If you want to enter for 2023, enter as Self-Employed Health Insurance Paid section under Wages & Income, even though the program says not to. It says not to because you can only deduct the net cost after any premium tax credit. When you file your 2024 tax return and complete form 1095-A, you may have to repay a portion of any premium tax credit you are receiving. Therefore, I recommend you wait and report it on your 2024 tax return.
As for your Cobra payments, if you paid those premiums with after tax funds, you can deduct them for any month you were self-employed. If they were deducted pretax from severance payments they are not deductible.
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