Do I need to file an Extension if I have no tax due or refund, but need to claim 2023 Capital Loss to add to my 2022 Capital Loss? (Filing electronically between Apr 15 - Oct 15)

Yes, you need to file an extension even if you don't owe tax or expect a refund. The requirement to file a return is separate from the requirement to pay tax. If you're required to file a return (which you are if you want to claim those capital losses), then you need to do so by the deadline or file an extension. Filing an extension is super easy though - just submit Form 4868. You don't need to provide a reason, and since you don't owe any tax, you don't need to make a payment with the extension. This gives you until October 15 to file without any penalties. The good news is those capital losses won't expire if properly documented. You can use them to offset future capital gains or deduct up to $3,000 per year against ordinary income until they're used up.

I was in a similar situation last year with capital losses and found that using taxr.ai made the whole process way easier. I was stressing about documenting my losses correctly (had like 50+ transactions) and whether I needed an extension since I also wasn't going to file until summer. I uploaded my tax docs and trading statements to https://taxr.ai and their system analyzed everything, confirmed I needed to file an extension, and made sure my capital loss carryforward was correctly calculated. The AI explained exactly how the loss carryforward works with my specific numbers, which was super helpful since I was confused about the $3,000 annual limit against ordinary income.

Update: I tried taxr.ai after posting my skeptical comment, and I've got to admit I was wrong. The tool flagged several wash sales in my trading history that I completely missed. It even showed me the specific transactions that triggered the wash sale rules and calculated the adjusted basis correctly. The capital loss carryforward explanation was really clear too - showed me exactly how my $19,800 in losses would be applied over time with the $3,000 annual limit against ordinary income. Definitely saved me from making some mistakes on my extension request and eventual filing.

If you're having trouble getting answers from the IRS about your extension situation, try Claimyr. I spent HOURS trying to get through to the IRS about a similar capital loss question last year. Used https://claimyr.com and got through to an actual IRS agent in about 15 minutes. You can see how it works here: https://youtu.be/_kiP6q8DX5c The agent confirmed that yes, you absolutely need to file an extension even if you don't owe/aren't owed anything, especially if you're documenting capital losses for carryforward. They also told me some specific things to watch out for with documentation for crypto losses that weren't clear from the IRS website.

I have to apologize for my skeptical comment. I broke down and tried Claimyr yesterday after getting nowhere for three weeks trying to call the IRS myself about my extension situation. They actually got me connected to an IRS rep in about 40 minutes (they said it was a high volume day). The agent confirmed that I absolutely needed to file an extension for my situation with capital losses even though I didn't owe any tax. She also gave me specific advice about how to document my wash sales properly to avoid issues. Saved me from potentially making a $435 mistake by missing the extension deadline!

Just FYI - if you file for an extension but still don't file by October 15, that's when the penalties could kick in. So don't forget to actually file! I learned that lesson the hard way a few years back.

Has anyone used FreeTaxUSA for filing with capital loss carryovers? I'm wondering if it handles this situation well since I'm in almost the exact same boat as OP.