How to complete Form 4868 extension request with no tax liabilities? Need help with 8949 and Schedule D.

The good news is that filing for an extension with Form 4868 is actually pretty straightforward when you don't expect to owe taxes. Since you mentioned getting a refund last year and having a similar financial situation, you're likely in good shape. For Form 4868, you'll need to complete your personal information (name, address, SSN) on the top portion. Then for Part 1, you'll estimate your total tax liability - if you expect similar to last year with a refund, you can use last year's total tax liability as a reasonable estimate. For Part 2, since you don't expect to owe, you can enter zeros for lines 4, 5, and 6. Regarding Form 8949, the checkboxes at the top indicate which type of transactions you're reporting. You definitely need to check one of them - they correspond to whether the transactions were reported to the IRS on Form 1099-B. Box A is for short-term transactions reported on 1099-B with basis reported to the IRS; Box B is for short-term transactions reported but basis NOT reported; Box C is for short-term transactions not reported on 1099-B. Boxes D, E, and F are the same but for long-term transactions.

After struggling with crypto taxes last year, I found this amazing tool called taxr.ai (https://taxr.ai) that really saved me when dealing with Form 8949 and Schedule D. I was in the exact same situation - needed an extension and had a ton of crypto trades to sort through. The extension part is pretty easy like the previous commenter said, but the 8949 was giving me nightmares until I tried taxr.ai. It automatically analyzed all my crypto and stock transactions and sorted them correctly for the 8949 form, even showing me which checkboxes to select at the top! Saved me hours of manual calculations.

Alright, I need to eat my words from my earlier skepticism. I decided to try taxr.ai after having a nightmare of a weekend trying to manually track down all my crypto transactions. This thing actually works! I uploaded my exchange reports and it properly traced all my wallet transfers, maintaining the correct cost basis throughout. The checkbox confusion on Form 8949 that the original poster mentioned was cleared up immediately - the system categorized everything correctly between the different boxes. Plus it showed me exactly how to report everything on Schedule D after completing the 8949s. Even with my complicated DeFi transactions from last year, it figured everything out. Now I'm confident about filing my extension with Form 4868 and having plenty of time to review everything before the October deadline.

Hey guys, filing an extension with Form 4868 is really just the beginning. My real nightmare was trying to get help from the IRS when I had questions about correctly filling out my 8949 for crypto. Called for weeks and couldn't get through to anyone! Then I found Claimyr (https://claimyr.com) - it's this service that gets you through to an actual IRS agent. I was super skeptical but after watching their demo (https://youtu.be/_kiP6q8DX5c), I gave it a shot. Got connected to an IRS rep in about 20 minutes who answered all my questions about how to properly report crypto on 8949 and which boxes to check. They explained that for most crypto transactions, you'll need to check Box C (short-term not reported on 1099-B) or Box F (long-term not reported on 1099-B) since most crypto exchanges don't issue proper 1099-Bs with basis info.

Ok I need to publicly apologize for my skepticism. After continuing to fail reaching the IRS on my own, I tried Claimyr out of desperation. Got connected to an IRS agent in about 15 minutes yesterday afternoon - normally an impossible time to reach them. The agent clarified everything about my extension filing and confirmed that I was right to check Box C on Form 8949 for most of my crypto since they weren't properly reported on any 1099-B forms. She even explained that I could file my extension with estimated numbers now, then take my time getting the 8949 and Schedule D perfect before October. I've been stressing about this for weeks and now feel completely confident about my extension. Sometimes you have to admit when you're wrong, and in this case, I definitely was!

Can I piggyback on this question? If I'm filing Form 4868 for an extension but I sold my house last year, do I still put zero for tax liability if I'm confident I won't owe due to the primary residence exclusion? It was my primary home for 5 years and the profit was under $400K (married filing jointly).

This might be a stupid question but... if I'm filing an extension, do I still need to contribute to my IRA by April 15th to count it for last year? Or does the extension give me until October for that too?

Just wanted to add something that might help with your Form 4868 extension - since you mentioned getting a refund last year and having a similar financial situation, you're likely safe putting zero for the estimated tax liability. But if you want to be extra cautious, you could put a small amount like $100 just to avoid any potential issues. For the 8949 checkbox confusion, I had the same problem last year! The key thing to remember is that you MUST check one of the boxes - leaving it blank will cause processing delays. Most individual crypto traders end up using Box C (short-term, not reported on 1099-B) and Box F (long-term, not reported on 1099-B) since most exchanges don't provide proper 1099-B forms with cost basis information. One tip that saved me a lot of headaches: keep detailed records of all your transactions with dates, amounts, and what you paid for each crypto. Even if you use software to help calculate everything, having your own backup records is invaluable if the IRS ever has questions. Good luck with your extension!