Deductions & credits

@dmertz  Thanks for the reply.  Where to pay expenses from has many factors, not just predicting the future.  What are the investment opportunities offered by the custodian?  Where would the money be drawn from instead and at what real and opportunity costs?  I am retired.  If I pull money from my IRA to contribute to the HSA, the distribution income is offset by the contribution.  If I need to pull an additional amount to pay the expenses, that is not offset.  I'd rather use the HSA funds and take that additional distribution (taxable) and convert to a Roth where I probably have more investment options, grows tax free, and can be withdrawn for any reason, not just medical, tax free.