I tried doing this last year and it backfired on me. My employer messed up the W-4 change and didn't withhold enough. Just make sure you check your paystubs after submitting the new W-4 to confirm the additional withholding is actually happening!!!

This is exactly what I did when I started my consulting work alongside my full-time job! One thing that really helped me was keeping detailed records of my 1099 income and expenses throughout the year in a simple spreadsheet. This made it much easier to adjust my withholding if my freelance income was higher or lower than expected. Also, don't forget that you can deduct business expenses from your 1099 income (home office, equipment, software, etc.), which will reduce the amount you actually owe taxes on. Make sure to factor this into your withholding calculations so you don't over-withhold. The key is to be conservative in your first year - it's better to get a small refund than to owe money and potentially face penalties. Once you get a feel for your actual 1099 income patterns, you can fine-tune the withholding amount for following years.

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.

I've had 570 codes three years in a row now. It's just part of the process for some of us. Usually clears up on its own, but if you have a 971 code too, watch your mail for a notice explaining what they need from you (if anything).

Don't panic! Code 570 is actually really common this year - I got it too about a month ago and my refund came through just fine. What helped me was checking for any accompanying codes on my transcript. If you see a 971 code with a date, that usually means they sent you a notice explaining what they're reviewing. Also, keep an eye on the "as of" date on your transcript - when that updates, it often means they're actively working on your case. The Child Tax Credit you mentioned is definitely a likely trigger since they're being extra careful with those this year. Hang in there - most 570 holds are resolved within 2-3 weeks!

Check your bank too. Not just WMR. Some banks hold IRS deposits. Mine shows pending two days early. Credit unions often faster. Big banks sometimes slower. Weekends delay everything. Tuesday DDDs are most reliable. Friday DDDs can mean Monday actual deposit. Transcript is most accurate source.

Great question! I've been tracking this pattern for the past few years as well. In my experience, WMR typically updates to "Refund Sent" about 1-2 days before your actual DDD, but there can be some variation. I've noticed that if your DDD falls on a Tuesday or Thursday (which are the most common IRS deposit days), WMR usually updates the night before or early morning of the day prior. However, if your DDD is on a Monday, it might update as early as the preceding Friday since the IRS doesn't process over weekends. One thing I've learned is that your transcript with the 846 code and DDD is always the most reliable source - that date is essentially set in stone once it appears. The WMR tool is more for general public updates and can sometimes lag behind their internal processing systems. Have you checked your transcript recently to see if your 846 code is showing yet?

Does anyone know if we need to convert the purchase price from foreign currency to USD when reporting on form 8949? I bought some UK stocks while living in London and the purchase was in GBP, but I sold after moving back to the US and received USD.

I had a similar issue with some European stocks I sold last year. The key thing to remember is that even without the 1099-B, you're still legally required to report all capital gains and losses. I used Form 8949 and checked Box C (transactions not reported to you on Form 1099-B) and entered all the details manually from my brokerage statements. One tip - if your broker is still "looking into it," get their response in writing via email. If the IRS ever questions the missing 1099-B, having documentation that you tried to get it corrected shows good faith effort on your part. Also make sure you have screenshots or printed copies of your account statements showing both the purchase and sale transactions as backup documentation. The deadline pressure is real, but don't let it rush you into making mistakes. Better to file correctly using your own records than to wait for a 1099-B that might never come.