Thanks, Sam. Very helpful. I had forgotten a lot of this and Wes is doing business taxes for his C-Corp this week and needed this info.

For post-tax contributions, my provider allows me to establish an automated monthly contribution. (And I have set up a monthly amount for this) Another option is a one-time contribution. The challenge with the latter is the amount of time, up to a week, for the funds to become available through the HSA debit card for qualified medical expenses. The trick is to balance the monthly contribution for guestimated expenses based on prior history and minimize the one-time contributions with a goal of always allowing for a positive balance to pay expenses. Of course, the total of all contributions need to fall under the maximum contribution amount for the current tax year.

One question I would have is would the employer be obligated to perform pre-tax contributions from an employee's pay per request to the HSA provider of the employee's choice? Or is the pre-tax distribution locked into the HSA provider that the employer chooses?

In researching HSA providers, I have found a huge range in fees and even management capabilities from one institution to the next. It was important for me to understand the impact of those fees from one HSA to another and the potential limitations imposed for each contribution method when I chose my provider.

In my case I enrolled in the company provided High Deductable Health Plan but declined the pre-tax contribution to the company provided HSA provider. I individually enrolled in an HSA of my choosing.

So in this scenario, would my employer be obligated to make those elected contributions from my pay to my HSA provider upon my request?

Great question. I do not know the absolute answer. The worst case scenario involves allowing the employer to contribute to the HSA provider that is part of the plan. Then, transfer the money to another HSA provider of your choosing. Please let us know what you find out.

I actually declined the withdrawals and make the contributions myself, post-tax to my HSA. Of course, pre-tax would be better for cash flow but the fees associated with the company selected provider were unreasonable and prohibitive.