This is great advice but what about cash transactions? I paid some of my business expenses in cash and have literally zero proof. Is there any way to claim those or am I just out of luck?

For cash transactions, you're in a tougher spot, but not hopeless. Try to find any indirect evidence - ATM withdrawal records from your bank statements that align with when you think you made purchases, any notes or calendar entries about what you were buying or why. The key is reasonableness - if you can show a pattern (like you regularly withdrew $200 in cash every month for business supplies), that's better than nothing. Just be honest and consistent with your reconstruction, and only claim what you're confident you actually spent. And in the future, either keep receipts for cash purchases (even taking a quick photo with your phone works) or use a credit/debit card for better tracking.

This is reassuring to hear! Was there anything specific that triggered your audit? I'm trying to figure out what to avoid so I don't get flagged...

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 suggestion! I actually did reach out to HR back when I left, and they told me any unused funds would be forfeited immediately upon my last day. I didn't realize at the time how this would affect my taxes or I would have tried to use the funds before leaving. Do you know if there's any time limit on when you can challenge this with HR? I left in August 2023, so it's been about 7 months now.

Unfortunately, if HR already confirmed the funds were forfeited upon your departure, there's likely little recourse at this point. Most plans have strict deadlines for submitting claims, typically 90 days after termination at most. After 7 months, it's almost certainly too late to challenge this with HR. Their policies about forfeiture upon termination are generally spelled out in the plan documents, and they have to follow those rules consistently for all employees. At this point, your best approach is what others have suggested - claim the dependent care credit for your expenses above the $3,300 amount shown in Box 10. While it's frustrating to lose access to money that was allocated for you, you can still benefit from the tax credit on your additional expenses.

Great question! There's an annual limit that applies across all employers for Dependent Care FSAs. For 2023, that limit was $5,000 for single filers or married filing jointly ($2,500 if married filing separately). If you've already participated in a DCFSA at your previous employer this year, you need to count those contributions toward your annual limit at your new job. For example, if you contributed $2,000 at your old job, you can only contribute up to $3,000 at your new employer for the year. Make sure to inform your new employer's HR about your previous FSA contributions so they can adjust your maximum accordingly. If you accidentally exceed the annual limit, it can create tax complications.

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!

Does TaxAct specifically handle the nominee distribution situation for inherited savings bonds? I've been using TurboTax but couldn't find this feature. Does it also file the 1096 form that needs to accompany the 1099-INTs?

Yes, TaxAct has a specific module for handling nominee distributions, including from savings bonds. When you indicate you received interest that partially belongs to someone else, it walks you through reporting your portion on your return and then helps you prepare the 1099-INTs for the other recipients. It also handles the 1096 form automatically as part of the e-filing process. If you choose to e-file these information returns, you don't need to worry about the red forms at all since everything is submitted electronically. TurboTax might have this feature too, but it's sometimes in their higher-tier packages.

I tried using the FIRE system last year and found it incredibly confusing. It's not designed for casual users or one-time filers. You need to follow very specific file format requirements and testing procedures. I ended up just paying a tax professional to handle it for me.