This is super helpful - thank you! I've been trying to format my spreadsheet to match the 8949 exactly but wasn't sure about the column order. Do you know if they care about the font size or anything like that? My PDF looks tiny when I try to fit all the columns on one page.

Font size isn't specified in the requirements, but I kept mine at 10pt to make sure it was readable. If it's too small, it might cause issues with their scanning systems. The key thing is consistent formatting throughout the document. I made sure each page had the same headers and columns. Also, make sure to number your pages (Page X of Y) at the bottom of each page. This helps if they're processing it physically. My tax professional said that consistent formatting is actually more important than font size.

I e-filed last year with around 18,000 crypto transactions. What worked for me was splitting it into 4 separate PDFs (organized by quarter) and attaching each one. I labeled them clearly like "Form 8949 Attachment 1 of 4 - Q1 Transactions" etc. My return was accepted without issues. Just make sure your summary lines on the actual 8949 form match the totals from all your attachments combined. The IRS systems can handle it as long as everything ties out properly!

Thanks for this - that's super helpful! I was about to just use Google Translate for the passport which sounds like it would've caused a rejection. Do you happen to know approximately how much a certified translator costs for passport documents? And is there any list of IRS Certifying Acceptance Agents for international locations?

Certified translation costs vary quite a bit depending on your location, but for passport documents, you're typically looking at around $40-120. Some translation services specialize in immigration and tax documents and may offer package deals specifically for ITIN applications. For IRS Certifying Acceptance Agents (CAAs) abroad, the IRS maintains a directory you can search by location at irs.gov/individuals/international-taxpayers/acceptance-agents-overseas. Not all countries have them, but major cities often do. If there's none in your spouse's country, some US-based CAAs can work remotely by video conference, though this is a newer practice that developed during the pandemic. One more tip: make sure the translator provides a signed statement of certification on letterhead that includes their credentials and a statement of accuracy. The IRS is quite particular about this.

Unfortunately there's no online tracking system for W-7 applications like there is for tax returns. You can try calling the IRS ITIN unit directly at 1-800-908-9982, but good luck getting through. I submitted my wife's W-7 in February and only got the ITIN letter in May. The only way I managed to check status was using that Claimyr service mentioned above to actually get through to an IRS agent. It's ridiculous how hard they make this process!

This is true but dangerous advice without context. Even if you're under the threshold, you might still want to file if you had any taxes withheld from paychecks because that's the only way to get a refund of that money. Also, certain credits like the Earned Income Credit require filing to receive them.

Can you explain more about these phase-outs? I've heard about QBI but my accountant said I probably can't use it because of my income level (around $225k).

The phase-outs start at $170,050 for single filers and $340,100 for joint filers (for 2022 tax year, slightly higher for 2023). Above those thresholds, the deduction starts to phase out for specified service businesses (legal, health, consulting, financial services, etc.). For non-service businesses, instead of phasing out completely, the deduction becomes limited based on W-2 wages paid and qualified property. This is where it gets tricky - sometimes paying yourself MORE in W-2 wages actually increases your QBI deduction if you're over the threshold. That's why personalized analysis is so important.

If you have an S-Corp, health insurance premiums paid for a >2% shareholder (which you would be) must be reported as income on your W-2, but then you get to deduct them on your personal return. It's a wash tax-wise, but requires the proper paperwork. For an LLC taxed as a sole proprietorship, you can take the self-employed health insurance deduction directly on your personal return without running it through payroll.

Thanks for raising this point! My divorce was finalized in 2017, so I'm still under the old rules where alimony is taxable income to me and deductible for my ex. That's why I need to figure out the correct year to report it.

Got it! Since you're under the pre-2019 rules, then yes, constructive receipt applies and the experts above are correct - it's 2023 income for you since you received and deposited the check in 2023, regardless of when the funds became available. Just make sure your ex is also treating it as a 2023 payment on their return to avoid any IRS matching issues.

But what if the bank hold was because of insufficient funds in the payer's account? That seems different from a standard hold.