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 Hi @TM78 

 Thanks for your question! I'd be happy to give you some guidance. HSAs are one of my favorite tax topics.

• Kudos on your HSA profits. Investing an HSA in the stock market and earning $ on top of your contributions is awesome!
• The earnings from your HSA are not taxable as long as you spend any HSA distributions on qualified medical expenses. 
• If you are under the age of 65, and you use your HSA on non-qualified medical expenses, then you are taxed on the entire distribution that was used on the non-qualified portion. Not only will the distribution be added to your total taxable income, thereby subjecting it to income tax, you'll also have to pay a 20% penalty! It doesn't matter whether the distribution is part of your contribution or part of the earnings.
• If you are age 65 or older, and you use your HSA on non-qualified medical expenses, then there is no penalty; however, your distribution will still be subject to income taxes.
• The $58k carryforward loss from your brokerage account is something that you don't need to consider in terms of your HSA. The loss will not have anything to do with the HSA.
• I encourage you to max out your HSA contribution every year that you qualify to do so. The money you don't spend carries forward so that you can use it for qualified medical expenses in the future. I use my HSA like this: I pay my medical expenses out of pocket, and I just hang on to my medical receipts. That way, my money stays in the HSA longer (earning more), and if I ever need to take a distribution later for cash flow purposes, I can do so, knowing that I have the medical receipts to back it up in case I get audited. 

I hope this information is helpful, @TM78! I'll stay tuned in case you have a follow-up question. Thanks again!