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How Do I Model Contributions to Health Saving Accounts?

We have not yet formally included HSAs in ESPlanner. We will likely do so in the near future. In the meantime, enter the contributions you plan to make as special expenditures that are excludable from AGI. That's really all you have to do. The future withdrawals are going to cover future medical expenses. You could enter the future withdrawals as non-tax related special receipts and the future medical expenses as non-tax related special expenditures, but they'll cancel with each other. So you might as well leave them both out of the program. best, Larry