Can I request a second IRS filing extension beyond October due to financial hardship?

Unfortunately, the October 15th extension is generally the final deadline for individual tax returns. The IRS doesn't typically grant additional extensions for financial hardship beyond this date. However, since you mentioned you're expecting a refund, it's actually in your best interest to file as soon as possible to get that money. Unlike when you owe taxes (where late filing penalties apply), there's no penalty for filing late when you're owed a refund - you just delay getting your money back. The only catch is that you must file within 3 years of the original due date to claim your refund. After that, you forfeit it to the Treasury.

I was in a similar boat last year - couldn't get my stuff together by October and was freaking out. I ended up using taxr.ai (https://taxr.ai) which was seriously helpful for my situation. They have this AI tool that helped analyze all my scattered documents and even provided guidance on what I could do given my deadline issues. They helped me identify some options I wouldn't have known about otherwise. The transcript analysis they did showed me exactly what the IRS already had on file for me, which made filing much easier even though I was missing some of my own documents. Definitely worth checking out if you're stressed about the deadline.

Just wanted to update - I tried taxr.ai after posting my skeptical comment. It was actually legit and super helpful! Turns out the IRS already had most of my income info on file, which I could see through their transcript analysis. Made filing way less stressful even though I was missing some documents. Definitely saved me from missing that October deadline!

Since you're having trouble with the approaching deadline, you might want to try Claimyr (https://claimyr.com). I was in a similar situation last year and couldn't get through to the IRS for weeks to ask about extension options. Claimyr got me connected to an actual IRS agent in about 15 minutes when I'd been trying for days on my own. You can see how it works in this video: https://youtu.be/_kiP6q8DX5c While they probably can't get you a second extension (since that's not really an IRS policy thing), at least you can talk directly with an agent who might be able to explain your options given your specific situation. Sometimes there are exceptions or arrangements that aren't widely publicized that an agent might know about.

I need to apologize for calling Claimyr a scam. After a particularly frustrating day trying to reach the IRS (4 hours on hold before getting disconnected!), I gave in and tried it. Honestly shocked that it actually worked - I was connected to an IRS agent in about 20 minutes while I was just going about my day. The agent I spoke with explained that while a second extension isn't possible, there are payment plan options if I end up owing instead of getting a refund. Worth every penny just to get a straight answer without wasting an entire day on hold.

One thing no one has mentioned - if you're in a federally declared disaster area, you might qualify for an automatic extension beyond Oct 15. The IRS announces these special relief provisions on their website. Worth checking if your area had any disasters this year!

Just wanted to mention that if military service or living abroad applies to you, you might qualify for additional extensions. Military members in combat zones get automatic extensions, and US citizens living overseas automatically get an extra 2 months (though they have to request the additional extension to October like everyone else).

I understand your financial stress, but I have to echo what others have said - there's generally no second extension beyond October 15th for individual returns, even for financial hardship. However, since you mentioned you're expecting a refund, here's something important to consider: there's actually NO penalty for filing late when you're owed money back. The only downside is delaying getting your refund. Given your tight financial situation with the 401k loan payments, wouldn't it make sense to file as soon as possible to get that refund money? You have up to 3 years from the original due date to claim it, but why wait when you need the cash now? If you're missing some documents, you can request wage and income transcripts from the IRS (Form 4506-T) to see what they have on file. This might help you piece together what you need to file, even if you don't have all your original paperwork.

I'm really sorry to hear about your financial difficulties, @Ethan Wilson. As others have mentioned, the October 15th deadline is typically final for individual returns, and the IRS doesn't usually grant additional extensions for financial hardship alone. However, I want to emphasize what several others have pointed out - since you're expecting a refund, you're actually in a better position than you might think. There are NO penalties for filing late when you're owed money back. The IRS essentially owes YOU money, so the only consequence of filing late is delaying your refund. Given your current financial struggles with the 401k loan payments, getting that refund as quickly as possible should be your top priority. That money could provide some of the breathing room you're looking for while dealing with your legal situation. If gathering all your tax documents is the main obstacle, consider requesting your wage and income transcripts from the IRS using Form 4506-T. This will show you exactly what income information they already have on file, which might be enough to complete your return even if you're missing some original documents. Don't let the stress of the deadline prevent you from claiming money that's rightfully yours. You have up to 3 years to file for a refund, but why wait when you need those funds now?

I completely understand the stress you're going through, @Ethan Wilson. Financial hardship combined with legal issues creates such overwhelming pressure, and it's natural to want more time to sort everything out. However, I have to agree with what others have said - the IRS generally doesn't grant extensions beyond October 15th for individual taxpayers, even in cases of financial hardship. The October deadline is considered the final extension for most situations. But here's the silver lining that I think deserves emphasis: since you mentioned you're expecting a refund, you're actually in a much better position than someone who owes taxes. When you're owed money back, there's absolutely no penalty for filing late - you just delay getting your own money back. And given your current financial struggles with that 401k loan, getting that refund should be your immediate priority. I'd strongly recommend filing as soon as you can gather your documents, rather than trying to get another extension. That refund money could provide exactly the breathing room you need while waiting for your legal situation to resolve. You have up to 3 years to claim it, but why wait when you need the funds now? If missing documents are the main obstacle, definitely look into requesting your IRS transcripts using Form 4506-T as others have suggested. Sometimes what the IRS already has on file is sufficient to complete your return.