Thanks for this explanation! Yes, the site did take a small fee during the conversion to ETH. Should I be including that fee in my calculations somehow? Sorry if that's a dumb question, I'm still trying to wrap my head around all this.

That fee is important! It should be factored into your cost basis. For example, if you withdrew $1000 worth of winnings but only received $950 in ETH after the fee, your cost basis should be $950, not $1000. When you eventually sell that ETH, you'll calculate your gain/loss based on the $950 figure. The $50 fee isn't deductible separately - it's just part of the transaction cost of acquiring the ETH. This is likely contributing to why your software is showing a capital loss.

How did you figure out the exact price when you received it though? The price can change like every minute and im never sure what exact value to use.

@Juan Moreno Good question! I usually just use the price from a major exchange like Coinbase or Binance at the time I received the transaction. Most crypto tax software will pull historical prices automatically if you enter the date and time. If you re'not sure about the exact timing, check your email confirmation from the gambling site - they usually timestamp when the withdrawal was processed. That s'the moment you acquired "the" crypto for tax purposes. You can then look up what BTC/ETH was trading for at that specific time on sites like CoinGecko or CoinMarketCap.

How do you even find out what your plan's minimum retirement age is? My old employer went out of business and the plan is now managed by some third party administrator who never answers the phone.

You can usually find your plan's minimum retirement age in the Summary Plan Description (SPD) that you should have received when you enrolled in the plan. If you don't have this document, try looking for online account access with the third-party administrator - they often have plan documents available for download. If those options don't work, try sending a certified letter to the administrator specifically requesting the Summary Plan Description and information about the minimum retirement age. By law, they must respond to formal requests for plan documents. Another option is to check if your disability payments changed amount when you reached a certain age - that change often coincides with the minimum retirement age.

This is super helpful! I've been trying to figure out if my payments are fully taxable or not. How do I know if I made "after-tax contributions"? I honestly can't remember from 30 years ago when I was working...

Great question! If you made after-tax contributions, they would have been deducted from your paycheck AFTER income taxes were already taken out (so you paid tax on that money when you earned it). Most employer pension plans only accept pre-tax contributions, but some allow after-tax too. Check old pay stubs if you have them - after-tax pension contributions would be listed separately from regular pre-tax retirement deductions. You can also contact your former employer's HR department or the current plan administrator to ask for your contribution history. They should have records showing the breakdown of pre-tax vs after-tax contributions you made over the years. If you can't find any records and you're not sure, it's safer to assume all contributions were pre-tax (which means 100% of your payments are taxable). Most people never made after-tax contributions to employer plans.

Comparing my experience this year to last year confirms this. Last year I had a straightforward W-2 return and got my refund in 8 days flat. This year I have 1099 income, business expenses, and home office deductions - suddenly I'm at 31 days and counting. It's not because I'm checking more often, it's because my return is more complex and probably in a different processing queue.

Do these Thursday night updates apply to everyone or just certain processing centers? I've read somewhere that different regional centers have different update schedules. My return is processing in the Kansas City center if that matters.

From my experience working with clients across different regions, the Thursday night transcript updates are generally system-wide, but processing centers do have slight variations in timing. Kansas City typically processes between 1-3am CT (2-4am ET), so you might see updates slightly later than East Coast filers. The regional differences are more about which batches get processed first rather than completely different schedules. Have you noticed any pattern in when your transcript has updated in the past, or is this your first time monitoring it closely?

omg great idea! doing this rn