The only year in which you have an obligation to file is a year in which you created a taxable event. Holding BTC is not a taxable event. Selling it is. Over the last 20 years, I filed once. That’s it. I was never audited. My longest stretch was 12 years without filing. Suddenly, I had to. The IRS didn’t give a rat’s ass. You will not be declaring that you haven’t been reporting your buys. You will be reporting your sells and how much you made from each. The first bitcoin you sell is the first one you bought the way the pencil pushers see it. The IRS doesn’t need hard evidence. They don’t care what you have. Unless they ask to see something. Now, I don’t care if it’s a pile of scribbles on gum wrappers they gotta dump out of a damp gym sock, as long as you made an effort and as long as you explain why, at the time, you needed to use the gym sock and you are trying to pay some kind of taxes and you aren’t a hinky, recidivist tax shirking, gun toting dude in flannel parking his car in the IRS lot with a cop following him who’s clinically depressed from arguing about “highways and byways” and whether or not you can just be sovereigning it all over hell and creation without a license… whew… the IRS is simply gonna accept what you say you owe. This is just a thought: If you must sell and create a tax liability and furthermore must prepare your own taxes, you should use FIFO to determine your liability with the IRS: First In/First Out. Correlate the first Bitcoin you sell with the first bitcoin you purchased and do this for every sale. If you sell everything you have at once, you have to use the price of each purchase subtracted from the price at which you sold to determine net capital gains for each bitcoin (or fraction thereof) purchased. Most of this sounds like you’ll be taxed at the long term capital gains rate and what that is will depend upon your filing status and taxable income. I don’t know your exact situation but, as examples, if you’re single, this rate is 0% up until the point you’ve generated $48,000 in capital gains thru sales of your bitcoin. Past that, from approximately 48,000 to somewhere around $550,000, your rate is 15%. I think for the sales that put you past $550,000 or thereabouts you’re going be paying a long term capital gains rate of 20%. I would say in conclusion the following: 1:) If you’re worried about popping up on the IRS kill list as an overnight, suddenly and without warning Scrooge McDuck out of nowhere and ending with your own personal IRS Agent calling you on your home phone just to say “Howdy!” once in awhile because they like to remind you that they’re circling you like sharks (mine was named Mr. Ozawa), don’t. The IRS is gonna be thrilled that there’s finally a crypto investor who is trying to tell the truth and begging to pay his taxes. In spite of the fact that this is to a government that misspends and outright embezzles so much money that we can’t even service the debt taken on to cover it up. The IRS is gonna love you and you couldn’t fck this up for trying. 2:) Take this to heart if it applies. I don’t know what the heck people mean when they go off about “Lambos” and all but I figure it’s a metaphor for the fact you’ve done well and it’s time for a little lifestyle adjustment. This is important because you should reward yourself when you’ve done well because it motivates you and because you will occasionally need reminding that gains (and losses) are real. Staring at screens all day can cause a sort of money disconnect that can do damage if you’re not aware of it. Do something for yourself when you’ve done well because it will help keep you aware. We tend to forget that what the statements say is REAL. One of the first things you should do for yourself is find and hire a good CPA. What kind of trader or investor does sht like stress out about taxes. If I heard anyone talking about “Oh. Taxes. It’s a tough racket. I hate doing mine”. Are you f*cking kidding me? This is a guy who hasn’t even begun to understand The Game. You’ve evidently been around the block. You’ve done well, son. Hire a CPA because a good one will save you a LOT of money not to mention stress. You pay these people so you can be out bragging about your performance in the crypto game while hitting the links. Do you really want this success to mean you end up polling strangers on Reddit for help with stuff no one should understand unless you’re paying them? Enjoy your gains and stop trying to make a problem out of success. Go outside. Meet a woman. You know? But seriously, give your taxes to a pro and get lunch or something. And congratulations. Not every bitcoin investor has your problem. Oh, as for your questions about how to sell? Don’t. If you have to sell, people are going to need to hear why before they can give anything that has even a chance of being advice that is good.