This is incredibly helpful - thank you for sharing! I've been struggling to reach the IRS about a 1099-R issue from my 401k rollover and kept getting the "high call volume" disconnect. One thing I'd add for anyone trying this: make sure you have a pen and paper ready when they call back. The agent I spoke with (using a similar method) gave me a lot of important information quickly, and I almost missed some key details about reporting requirements. Also, for those worried about wait times - I've found that if you miss their callback, they don't automatically reschedule you. You have to start the whole process over, so definitely keep your phone close and answer unknown numbers during your callback window! Has anyone had success using this method for questions about estimated tax payments? That's my next hurdle to tackle.

This is exactly what I needed to see! I've been putting off calling about my backdoor Roth IRA conversion reporting because I was dreading the phone maze. A few questions for anyone who's used this method recently: 1. Do they ask what your call is about when you first get connected, or do they wait until the callback? 2. If I have multiple tax years to discuss (2022 and 2023), should I mention that upfront or focus on one issue at a time? 3. Has anyone tried this for questions about Form 8606 specifically? I want to make sure I don't get transferred around between departments. I'm planning to try first thing Monday morning (7:05am sharp based on everyone's advice). Really appreciate this community for sharing these practical tips - the IRS website is basically useless for actually getting help!

I completely understand your frustration, Hunter! I went through this exact same process a few months ago and felt like I was going in circles. What helped me was realizing that there are actually TWO separate things happening: 1) Having an ID.me account (which you already have), and 2) Authorizing that account specifically for IRS access. Think of it like having a driver's license but still needing to register to vote - they're related but separate steps. The key is making sure you complete that authorization step when you log in through the IRS website. Once I understood this distinction, the whole process made much more sense. You've got this!

Hunter, I completely feel your pain on this! I just went through the exact same thing two weeks ago and was pulling my hair out. What finally worked for me was going to irs.gov, clicking "Sign into Your Online Account," then selecting ID.me, and here's the crucial part - when it asks you to authorize the IRS to access your ID.me information, you HAVE to click "Allow" or "Authorize." I had been logging into ID.me successfully but kept missing that final authorization screen. It's like having the right key but forgetting to actually turn it in the lock! The whole process took me about 10 minutes once I realized what I was missing. Don't give up - you're probably closer than you think!

I just want to warn everyone not to skip reporting crypto, even if you think the IRS won't know. I did that in 2021 because I had a small loss and didn't get any tax forms, and I got a CP2000 notice last year saying I owed taxes plus penalties. Apparently my exchange DID report my transactions to the IRS using some form I never received. Had to pay about $800 more than I would have if I'd just reported correctly in the first place. Don't make my mistake!

Just to reinforce what others have said - yes, you absolutely need to file Form 8949 even without a 1099-B. I'm a tax preparer and see this situation constantly with crypto clients. The key thing to understand is that cryptocurrency transactions are treated as property sales by the IRS, so every sale triggers a taxable event regardless of whether you received tax documents. Your $3,200 loss is actually valuable - it can offset other capital gains or up to $3,000 of ordinary income. For H&R Block, when it asks about the 1099-B, select "transactions not reported on Form 1099-B" and check box C on Form 8949. You'll need to manually enter each transaction with purchase date, sale date, proceeds, and cost basis. Keep detailed records of all your transactions - the IRS is increasingly focused on crypto compliance and many exchanges do report to them even if they don't send you forms. Don't risk an audit by not reporting. The penalties for underreporting are much worse than the time it takes to fill out the form properly.

Don't forget that even though you have to report all income, you can also deduct your expenses which will lower your taxable income! For delivery driving, track all your miles (including miles between deliveries) - that's usually the biggest deduction. Also, you can deduct a portion of your phone bill, insulated bags, car maintenance, etc. I did Instacart last year and after deductions, my taxable income was much lower than my gross earnings. Just make sure you keep good records in case you get audited!

Just a heads up, the threshold for receiving a 1099-K was supposed to change to $600 for 2024, but the IRS delayed it again. So for 2024 taxes (filing in 2025), third-party payment networks only have to send 1099-Ks if you made over $20,000 AND had more than 200 transactions. This might be why you don't receive forms from some gig apps. But remember - and this is super important - you still legally have to report ALL income regardless of whether you get a tax form!

This is such a comprehensive discussion! As someone who recently went through a similar international move, I wanted to add a few practical considerations that might be helpful. One thing that really helped me was creating a "domicile transition checklist" to ensure I was consistent in establishing my new foreign domicile. This included things like: - Opening local bank accounts and making them your primary accounts - Getting local phone service and utility accounts in your name - Registering with local tax authorities in Singapore - Getting a local driver's license (if you plan to drive there) - Joining local clubs, gyms, or community organizations - Establishing relationships with local service providers (doctors, dentists, etc.) The key insight from my tax attorney was that the IRS looks for a "preponderance of evidence" - they want to see that the majority of your life connections point to your new country rather than the US. Since you're keeping your NYC apartment unfurnished and not renting it out, document this decision well. Having it sit empty (rather than being set up as a home you could immediately return to) actually supports the argument that Singapore has become your primary domicile. Also consider the timing of your move - if you move mid-year, you might benefit from filing as a dual-status taxpayer for that transition year, which could optimize your tax situation. Good luck with your move! Singapore is an amazing place to live.

This has been an incredibly informative thread! As someone who works in international tax compliance, I wanted to add a few technical points that might help clarify the domicile vs. tax residency distinction for @Chloe Martin and others in similar situations. First, it's important to understand that "domicile" and "tax residency" are actually separate concepts, though they often overlap. Domicile is more of a legal concept about your permanent home and intent, while tax residency can be determined by various tests (physical presence, closer connection, etc.). For US citizens, you'll always be subject to US taxation on worldwide income regardless of domicile - but establishing foreign domicile can be crucial for: 1) Qualifying for Foreign Earned Income Exclusion 2) State tax purposes (as others mentioned) 3) Estate planning implications 4) Potential future expatriation decisions Regarding your specific Singapore situation - the lack of a tax treaty actually makes documentation even more important. Without treaty protections, you want to be absolutely clear about your status to avoid any double taxation issues. One practical tip: consider getting a formal legal opinion from a tax attorney about your domicile change, especially given the value of NYC real estate. The cost upfront could save significant issues later if the IRS questions your position. The physical presence test for Foreign Earned Income Exclusion (330 days in any 12-month period) might be easier for you to meet than the bona fide residence test initially, so track your days carefully from day one of your move.