What kind of detailed records do you recommend keeping? Is a credit card statement enough or do I need actual receipts for everything? I'm terrible at keeping track of paper receipts.

Credit card statements are a good start, but they're not enough on their own. The IRS wants to see the business purpose of each expense, which doesn't show up on credit card statements. I use a combination of methods - I take photos of paper receipts using an app that stores them digitally, save PDF receipts from online purchases, and maintain a spreadsheet where I note the business purpose of each purchase. For software subscriptions, I note what each one is used for in my business. The key information you need for each expense is: date, vendor, amount, what was purchased, and specific business purpose. Digital records are perfectly fine - you don't need to keep paper copies as long as your digital records show all this information.

What's this $2,500 threshold you mentioned? Does that mean I can deduct equipment purchases up to $2,500 immediately without depreciating them? That would be super helpful to know!

So how long does it typically take for the IRS to get the updated info from SSA after you get your new card? Is it immediate or is there like a delay of weeks/months?

It's usually not immediate. The SSA and IRS data synchronization typically happens within 2 weeks after your new card is issued, but in some cases it can take up to a month. However, you don't need to worry about the exact timing. Once you receive your new Social Security card with your updated name, that's your confirmation that the change is official with the SSA. For any tax filings after that point, you should use your new name as it appears on your card.

Is there any way around this? Like can she file a paper return with her married name instead of electronic filing? My sister had a similar issue.

Thanks for sharing your experience! Do you think having the previous counter offer will help his case? Also, did you have to provide any special documentation that might not be obvious?

The previous counter offer is absolutely golden - it shows the IRS was already willing to settle. He should definitely include all documentation from that previous interaction and reference it prominently in his new submission. As for non-obvious documentation, medical bills were huge in my case. The IRS allows for necessary medical expenses, but most people don't document them thoroughly enough. Have him gather EVERY prescription, doctor visit, and medical expense for the past year. Also, if he has any unusual expenses that aren't on the standard IRS forms (like caring for an elderly parent, special education needs for children, etc.), he needs to document these with receipts and explanations. The IRS can be surprisingly reasonable about legitimate unusual expenses if they're properly documented.

What tax software would you recommend for someone wanting to DIY an Offer in Compromise? Can regular software like TurboTax handle this or do you need something special?

I used TaxSlayer last year and it doesn't have OIC forms. Had to do those manually. Not sure about other programs though.

I did file a police report actually! The officer wasn't super familiar with crypto theft but took all the details. I also reported it to the FBI's Internet Crime Complaint Center (IC3) online. Not sure if anything will come of it, but at least I have documentation that I reported it officially. Do you think I should include copies of these reports with my tax return? Or just keep them on hand in case of audit?

I would definitely keep the police report and IC3 complaint with your tax records, but you don't necessarily need to include them with your filed return. Having those documents will be extremely helpful if you're ever questioned about the loss. My accountant also suggested writing a brief statement explaining the theft that you can attach to your return - just a simple explanation of what happened, when it happened, and that you filed reports. This shows you're being transparent and proactive.

I used Koinly for a similar situation. You can manually add a transaction and mark it as "lost" or "stolen" which helps with the reporting. You'll still need to double-check everything because the software isn't perfect with edge cases like theft.

Thanks for this explanation. Does this mean I've been doing something wrong the past few years? Will this cause problems when I apply for OPT after graduation?

If you've had mixed income (both W-2 and treaty-exempt 1042-S) and didn't report the 1042-S income on your returns, you might want to consider filing amended returns. The good news is that if you didn't owe additional tax (because the income was truly treaty-exempt), you likely won't face penalties other than possibly interest on late payments if any portion was actually taxable. As for OPT applications, USCIS doesn't typically verify tax compliance for OPT specifically, but they may check this for later immigration benefits like H-1B or permanent residency. They're mostly concerned that you maintained status and followed visa regulations. If you're worried, consulting with an international tax specialist would be worthwhile before your OPT application.

Does Glacier work for alumni too? I graduated last year but still got a 1042-S for a final scholarship payment in January.