Slightly off topic but why are u paying $12.99 per trade in 2025? Almost all major brokers offer free stock trades now. Unless ur trading something unusual or international?

Just wanted to add a point that might help others - make sure to keep detailed records of ALL your brokerage fees throughout the year, not just relying on your 1099-B. I learned this the hard way when my broker's year-end statement was missing some fees from smaller trades. I now keep a simple spreadsheet tracking each transaction with the actual purchase/sale price and the fee separately. This way when tax time comes, I can verify that my cost basis calculations are correct regardless of what the brokerage reports. Also, if you're doing a lot of trading like the OP mentioned, consider whether you might qualify as a trader for tax purposes rather than an investor - the rules for deducting expenses can be different and potentially more favorable.

My tax person said the deposit date on the transcript is when the IRS is done with their part. Then it goes to the financial management service who actually sends the money to banks 1-2 days before. Then its up to your bank when they let you have it.

This is so helpful! I've been stressing about my 2/17 date all week. I have Capital One 360 - does anyone know if they do early deposits like Chime? I'm hoping to see something before Monday but not getting my hopes up since it's not one of the "big" early deposit banks.

For what it's worth, Koinly helped me sort through a similar mess. I had hodled since 2017 and never reported anything. Their historical price data was pretty accurate for calculating my cost basis on old transactions, which was my biggest concern. Think they have a free tier where you can import everything first to see if it works before paying.

You're definitely not alone in this situation - I see posts like this all the time here. The good news is that the IRS has been pretty understanding about crypto confusion, especially for people who are genuinely trying to get compliant. A few practical steps to get started: 1. **Prioritize recent years first** - Focus on 2021-2023 since those are most likely to be audited and have the biggest impact 2. **Gather what you can** - Download transaction histories from all your exchanges going back as far as they allow. Most keep records for several years 3. **Don't stress about perfection** - The IRS prefers a good faith effort over perfect precision. If you can't find every single transaction from 2016, document what you tried and work with what you have 4. **Consider professional help** - Given the complexity and potential tax liability, a crypto tax specialist might save you money in the long run, especially for the voluntary disclosure process The key is starting the process now rather than waiting longer. Each year you delay just makes it more complicated and potentially more expensive. Most people in your situation end up owing less than they feared once everything is calculated properly, especially if you've been mostly holding rather than actively trading.

Is anyone using tax software to figure this out? I tried entering my kid's braces expenses in TurboTax but it's not clear if I'm doing it right. It keeps asking me if the expenses were for "dental services" or "medical services" and I don't know which category braces fall under.

Just wanted to share my experience as someone who went through this exact situation! My orthodontist actually gave me a really helpful tip - if you're doing a payment plan, you can strategically time your payments to maximize your deduction in a high-income year. For example, if you know you're going to have a bonus or higher income one year, you might want to prepay more of the orthodontic treatment in that year since the 7.5% AGI threshold will be harder to reach. Conversely, if you have a lower income year (maybe due to job loss or reduced hours), that might be the perfect time to bunch your medical expenses since you'll hit the threshold more easily. Also, don't forget about related expenses! You can deduct mileage to and from orthodontic appointments (currently 22 cents per mile for medical purposes), and if you have to travel overnight for specialized treatment, even lodging can be deductible. These little things can really add up over the course of treatment. One last tip - if your employer offers an FSA or HSA, definitely use it for future orthodontic work since it's pre-tax money. You can't deduct FSA/HSA expenses on your taxes, but you're still getting the tax benefit upfront.

Based on everyone's advice here, it sounds like you're in good shape to use the summary approach since your cost basis was reported to the IRS. I'm in a similar boat this year with more trading activity than usual. One thing I'd add is to double-check that your wash sale adjustments are correctly reflected in the summary totals on your 1099-B. Sometimes brokers handle the presentation differently, and you want to make sure the adjusted gains/losses match what you're reporting. Also, even though you're using the summary, I'd recommend keeping a spreadsheet or copy of all the individual transactions somewhere safe. Not just for potential IRS questions, but also for your own records - it's helpful to have that detail if you need to reference specific trades later for other financial planning purposes. FreeTaxUSA should handle the summary input smoothly once you have the right totals. Good luck with your filing!

This is really helpful information! I'm dealing with a similar situation this year - first time having significant investment activity and was dreading entering hundreds of transactions manually. From what I'm reading, it sounds like the key factors are: 1) whether cost basis was reported to the IRS (check Box 3 on your 1099-B), and 2) making sure any wash sale adjustments are properly reflected in the summary totals. One question for the group - if I have multiple 1099-Bs from different brokerages, do I need to enter separate summaries for each one, or can I combine them into one total? All of mine show cost basis reported, but they're from different firms (Schwab and Vanguard). Also want to echo what others said about keeping detailed records even when using the summary approach. Better to have them and not need them than the other way around!