I went through this exact scenario with two different clients in the past year, so I completely understand your stress! Here's what I learned from those experiences: First, the rejection of your e-filed extension is actually normal when there's a disconnect between your filed return and the IRS's system records. This doesn't necessarily mean your S election was denied - it's more likely that their systems just haven't synced up yet. For immediate protection, definitely mail Form 7004 via certified mail and mark it as an S corporation extension. Include a brief cover letter explaining that you have a pending S election under review. This creates documentation of your good faith effort to comply. Regarding your short tax year dates (9/1/22-12/31/22), those were absolutely correct if that's when business operations actually began. Don't second-guess yourself on this - the IRS expects the first tax year to reflect actual business activity dates. One thing I'd recommend is getting a Power of Attorney (Form 2848) on file if you don't already have one. This will make it much easier when you call the IRS to check on the election status, as they can speak directly with you about your client's account. The good news is that even if there are delays, you can usually get retroactive relief if you can demonstrate reasonable cause for the late filing. Keep detailed records of all your submission attempts and communications with the IRS.

I've been through this exact situation multiple times with clients, and I want to reassure you that this is more common than you think, especially with the IRS processing delays we've seen lately. Here's my step-by-step recommendation based on what's worked for my clients: 1. **Immediate action**: Mail Form 7004 via certified mail TODAY if you haven't already. Check the S-corp box and include a brief statement that the S election is pending IRS processing. This protects your client from penalties. 2. **Verify election status**: Call the Business & Specialty Tax Line at 800-829-4933 first thing in the morning. Navigate to the Form 2553 department specifically. Have your client's EIN, business name, and the date you submitted the election ready. 3. **Don't panic about the dates**: Your 9/1/22-12/31/22 short year was absolutely correct since that's when operations began. This won't cause approval issues. 4. **System disconnect is normal**: The e-filing rejection usually means their systems haven't synced, not that your election was denied. I've had clients where the election was approved weeks before the e-filing system recognized it. The key is getting confirmation of your election status first, then you'll know exactly how to proceed. Most of these situations resolve favorably - it's just the waiting and uncertainty that's stressful. Keep detailed records of all your calls and submissions for your files. You've got this! Let us know what you find out when you call.

I went through this exact same situation with my mother's IRA last year and completely understand your frustration! The key issue is that tax software often treats "inherited IRA" as if you're maintaining an inherited IRA account, but you actually took a full cash distribution. Here's what worked for me in TurboTax: Answer "Yes" to inheriting the IRA, but when it asks about the type of distribution, specifically look for an option like "I took a complete/total distribution" or "lump sum distribution." This should bypass the basis questions that are causing the software to calculate incorrectly. The reason you're seeing that massive refund is because the software is likely applying inheritance rules meant for people who are stretching distributions over time or who inherited Roth IRAs where distributions might be tax-free. Since your brother-in-law likely had a traditional IRA with pre-tax contributions (most common), the entire distribution should be taxable income. Make sure the distribution code in Box 7 of your 1099-R is correct - it should indicate death/inheritance (usually code 4). If everything is entered properly, you should pay ordinary income tax on the full amount with no early withdrawal penalty. Don't feel bad about being confused - this is one of the most poorly designed parts of tax software!

You're absolutely correct on both points! Since you took the entire IRA as a lump sum cash distribution (rather than rolling it over), you'll pay ordinary income tax on the full amount, but there should be NO 10% early withdrawal penalty regardless of your husband's age. The fact that your 1099-R shows code 4 in Box 7 confirms this is properly coded as a death distribution, which exempts it from the early withdrawal penalty. When you find that "complete distribution" or "lump sum distribution" option in TurboTax, it should clear up all the confusion and stop the software from trying to apply Form 8606 or giving you that incorrect refund calculation. The software gets tripped up because it's trying to apply rules for people who are keeping the inherited IRA open and taking distributions over time, but that's not your situation. One tip: if you're still having trouble finding the right option, try looking for language like "I liquidated the entire inherited IRA" or "I closed the inherited IRA account" - different versions of tax software phrase this differently, but they all have some way to indicate you took everything out at once. You're handling this exactly right by wanting to pay the appropriate taxes on what is essentially new income. Once you get past this software glitch, your return should calculate normally with the inherited IRA amount added to your other income for the year.

Just to add another perspective - I work as a tax preparer and deal with signature issues all the time. The IRS has actually gotten much more flexible about electronic signatures since COVID, especially for individual returns (Form 1040). What matters most is that it's YOUR authentic signature, regardless of how it's created. A stylus signature on your Surface that gets printed is generally acceptable for most personal tax forms. The key is making sure the signature looks consistent with other documents you've signed. That said, if you're really worried about it, here's a middle-ground solution: sign a blank piece of paper with a pen, scan or photo it with your phone, then digitally paste that signature onto your tax forms before printing. This gives you a "wet signature" appearance while avoiding the transport issues. But honestly, for a standard 1040 return, your stylus signature should be fine. The IRS processes millions of returns and they're more concerned with tax compliance than signature methodology. Just make sure it's clearly your name and looks like an actual signature attempt, not just typed text.

As someone who's dealt with this exact situation, I'd say go with the stylus signature! I've been using my iPad to sign tax documents for the past two years without any issues. The IRS really has become much more flexible about electronic signatures, especially since so many people are doing everything digitally now. Your Surface stylus signature will be totally fine for a standard 1040 return. Just make sure it actually looks like your signature and not just scribbles. The IRS cares way more about whether you're reporting your income correctly than how you physically signed the paper. That said, definitely look into the Free File program for next year like others mentioned - no point paying TurboTax's fees if you don't have to! But for this year, sign it digitally, print it out, and mail it in. You'll save yourself the Uber money and the headache.

I've been using FreeTaxUSA for 3 years and never had this problem until this year. I think they're just overwhelmed with new users. If you keep getting errors, try this workaround that worked for me: 1. Clear browser cache/cookies 2. Use incognito/private browsing mode 3. Try the direct login URL: https://www.freetaxusa.com/login.jsp instead of going through the homepage The third step was what finally worked for me when nothing else did. Good luck!

I've been dealing with the same FreeTaxUSA login issues for the past week! What's frustrating is that I already started my return there and now I can't get back in to finish it. For anyone still struggling, I found that using a VPN sometimes helps - I think their servers might be geographically overloaded in certain regions. I switched my VPN to a different state and was able to get in during peak hours when it normally would have failed. Also, if you're like me and already have a partially completed return stuck in there, don't panic - your data is saved and you won't lose your progress once you can log back in. I called their support line (surprisingly short wait time compared to the IRS!) and they confirmed this. The direct login URL that Diego mentioned actually worked for me too, but only in combination with clearing cookies first. It's definitely worth trying all these suggestions before giving up and switching to a different service entirely.

I dealt with almost the exact same situation last year and wanted to share what I learned. The joint account aspect actually simplifies things quite a bit - since you're already a named account holder, the IRS typically views transfers between accounts you're on as internal movements rather than gifts. The key thing that helped me was treating this properly as debt repayment from the start. I created a simple spreadsheet listing all the expenses I'd covered for my parents (medical bills, home maintenance, utilities, etc.) with dates and amounts. Then I had my parents sign a one-page acknowledgment that they owed me this money and were repaying it. One thing I wish someone had told me earlier - keep records of how you originally paid these expenses. Bank statements showing transfers from your personal account to pay their bills, credit card statements if you used your cards, etc. This creates a clear paper trail showing you genuinely fronted the money on their behalf. Since you mentioned $130k over a couple years, that's substantial but completely reasonable for ongoing family support. Just document everything well and you should be fine. The IRS understands these family arrangements happen all the time - they just want to see that it's legitimate debt repayment rather than gift tax avoidance.

I've been following this thread and wanted to add my perspective as someone who works in banking compliance. The joint account situation actually works in your favor here - transfers between accounts where you're already a named holder rarely trigger gift tax scrutiny. However, I'd strongly recommend getting ahead of any potential banking flags by giving your bank a heads up about the transfer, especially since $130k will definitely trigger Currency Transaction Reports. Most banks appreciate when customers explain large transfers in advance rather than having to investigate them after the fact. One thing I haven't seen mentioned is that you might want to consider the timing of this transfer relative to your tax year. Since this is debt repayment rather than income, the timing shouldn't affect your taxes, but having it settled before year-end can make your record-keeping cleaner. The documentation everyone's suggesting is spot-on - create that paper trail showing the original expenses you covered, get your parents to sign an acknowledgment, and keep everything organized. Banks see these family financial arrangements constantly, so as long as you can explain the legitimate purpose of the transfer, you shouldn't have any issues.