That's a really good tip about saving the PDF first! Did you find their response times were quick enough to make this approach workable? And did you feel like they were thorough in addressing your questions?

The response times varied quite a bit. During off-peak hours (early morning or late evening), I usually got responses within 20-30 minutes. During peak times (weekends, evenings), it sometimes took 2-3 hours. I ended up submitting a bunch of questions before bed and checking the responses in the morning. As for thoroughness, it was mixed. Some experts gave really detailed answers with explanations about why certain tax rules applied to my situation. Others gave pretty bare-bones responses that didn't fully address my concerns. When that happened, I just asked follow-up questions until I got the clarification I needed. It definitely requires more persistence than the old appointment system, but I eventually got all the help I needed.

I used TaxSlayer last year and their Ask a Tax Pro service was ok but limited. You can ask questions but they don't do a comprehensive review. They give you like 3 questions with their mid-tier plan, and unlimited with their premium. Responses usually came within a day but sometimes felt generic.

Thanks for sharing your experience! That's disappointing to hear it's limited to a certain number of questions with their mid-tier plan. I definitely need more hand-holding than that. I might just bite the bullet and pay for a local CPA to review everything after I prepare it myself. Seems like all these online services are moving away from comprehensive reviews to save money on staffing costs.

Really? That would be so much easier! How did you calculate the difference in what you owed? Did you still use tax software to figure out the corrected amount or just calculate it manually?

I used TurboTax to calculate the correct amounts but didn't actually file an amended return through them. I basically entered all my original tax info plus the missing crypto transactions, saw what the new tax liability was, then compared it to my original return to get the difference. On the CP2000 response form, I entered my recalculated amount which was actually less than what the IRS estimated (they always seem to assume worst-case scenario on crypto gains). I included a brief explanation letter along with my completed Schedule D and 8949 showing all the transactions with correct basis amounts.

This is super important advice. The IRS is really backed up right now, but they don't extend the same courtesy to taxpayers. I learned this the hard way last year.

That's surprising! I work with a foundation and we never ask about which 501(c)(3) application was used. Maybe that foundation has had bad experiences in the past?

Does Free File handle multi-state returns though? Last time I tried it wouldn't let me add a second state without upgrading to a paid version.

It depends on which Free File partner you choose. Some providers do limit the number of state returns, but not all of them. I used OLT (Online Taxes) through the Free File program last year and was able to file federal plus three state returns completely free. TaxSlayer also lets you file multiple states through Free File without extra charges. Just make sure you access them through the official IRS Free File portal rather than going directly to their websites, as the free offers are different.

That's really risky. The IRS gets copies of ALL W2s and their system automatically flags mismatches. You might have gotten lucky last year, but it could easily come back to bite you with penalties and interest that would cost way more than whatever you saved.

Thanks for the professional perspective! So if the form is filed and the IRS doesn't respond within the 18 months, does that mean they can't come after anyone later if they find an issue? And does filing this form increase the chances of getting audited compared to not filing it?

If the IRS doesn't assess any additional tax within the 18-month period, they generally can't come after the estate or the personal representative after that time has elapsed. There are exceptions for fraud or significant understatements of income, but for a straightforward estate like you described, those wouldn't apply. Filing Form 4810 doesn't increase audit risk in my experience. The IRS doesn't view it as a red flag - it's a standard administrative request. They process thousands of these forms, and they don't trigger special scrutiny. Many tax professionals consider it good practice to file this form precisely because it limits liability exposure.

Massachusetts resident here. When we settled my grandmother's estate last year, our attorney filed the Form 4810 for federal purposes while acknowledging that MA still maintains their own 3-year period for state tax purposes. The two timeframes operate independently - shortening the federal period doesn't affect the state period at all.