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Kiara Greene

Need urgent help! Started S Corp but can I file as Sole Proprietor for tax years 2021-2022?

I'm seriously stressing out about my tax situation and need some guidance from anyone who's been through this. In mid 2021, I started doing some contracting work as a side gig. Things were going well enough that I kept it up through 2022. At some point, this bookkeeper I hired (total waste of money, btw) convinced me that forming an S Corporation would be the best move tax-wise. So I went ahead with it without really understanding what I was getting myself into. Fast forward to now, and I've got a complete mess on my hands. I mixed personal and business finances constantly, filed extensions for both years, and my QuickBooks subscription lapsed when I stopped paying for it after realizing the bookkeeper wasn't doing anything with it anyway. So now I don't even have proper records! What I really want to know is: can I just ignore the S Corp filing and do my 2021 and 2022 taxes as a Sole Proprietor instead? Would that be simpler given the mess I'm in? I talked to someone at Justice Tax recently, but I'm not totally confident in their advice and wanted to get some additional perspectives before making any decisions. The tax deadline with extensions is approaching and I'm getting really anxious about this!

Evelyn Kelly

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You're in a tricky situation, but don't panic! Once you've elected S Corp status and filed with the IRS, you generally need to file as an S Corp. The problem is that the S Corp is now a separate legal entity that exists whether you maintained it properly or not. Here's what you need to know: If you formed the S Corp and started operating under it, you technically need to file Form 1120-S for the corporation and then report any distributions or salary on your personal return. However, if you never actually operated as an S Corp (never opened separate accounts, never processed payroll, essentially just formed it but didn't use it), you might have some options. Your best approach might be to get a tax professional who can help you determine if you have grounds for "late election relief" to be treated as a sole proprietor, or if you should just properly file the S Corp returns. Mixing finances makes this more complicated, but it's fixable.

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Kiara Greene

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Thanks for responding! I did operate under the S Corp name and had clients pay the business directly, but I never set up proper payroll or took an official salary. Just kind of transferred money from business to personal accounts whenever I needed it. Would that complicate things further?

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Evelyn Kelly

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Yes, that does complicate things a bit more. Since you operated under the S Corp name and had clients paying the business directly, the IRS would consider the S Corp active. The transfers you made should have been structured either as salary (requiring payroll taxes) or as distributions (which have their own tax implications). For an S Corp, the IRS expects you to take a "reasonable salary" subject to employment taxes, before taking any distributions. Those improper transfers between accounts could potentially be classified as distributions without adequate salary, which is something the IRS often looks at.

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Paloma Clark

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Just wanted to share my experience with a similar situation. After spinning in circles trying to fix my own S Corp tax mess, I ended up using https://taxr.ai to help straighten everything out. What was super helpful was that they analyzed my bank statements and could categorize all those mixed transactions between personal and business accounts that I had no idea how to handle. They actually specialize in sorting out messy books for small business owners. The system helped me recreate proper books for my past filings, showing me which transactions should be classified as legitimate business expenses versus personal withdrawals. Made a huge difference in getting my S Corp filing prepared correctly.

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Heather Tyson

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How long did it take them to sort through all your transactions? I'm in a similar situation with about 18 months of mixed finances and I'm worried it would take forever to untangle.

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Raul Neal

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I'm skeptical about these online services. Did they actually help with filing the returns or just organizing the data? Because it sounds like OP needs help with the actual tax forms and potentially dealing with the IRS about the election status.

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Paloma Clark

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It took about 2 days for them to process all my transactions, which was about 14 months worth. They have some AI thing that recognizes patterns in your spending which really speeds things up. They don't file the returns themselves but they organize everything into reports that make it super simple to either DIY your filing or hand to an accountant. In my case, I took their reports to my accountant who was amazed at how organized everything was compared to the mess I'd brought him previously. Saved me a ton on accounting fees since he didn't have to do all that cleanup work.

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Heather Tyson

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Just wanted to follow up - I tried taxr.ai after seeing this recommendation and it was seriously helpful! I had almost 2 years of completely mixed finances between personal and my LLC accounts. The system identified patterns in my spending and automatically categorized about 80% of my transactions correctly. I just had to review and fix the remaining ones. What I really liked is that it showed me exactly which "personal" transfers should actually count as owner distributions versus legitimate business expenses. It even flagged potential red-flag deductions that might trigger an audit. Ended up with clean books that I could actually hand to my tax preparer without embarrassment. Definitely worth checking out if you're in a similar mess!

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Jenna Sloan

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One thing nobody's mentioned yet - if you're struggling to get answers from the IRS about your options, try using https://claimyr.com to get through to an agent. I was in S Corp hell last year trying to fix some filing mistakes and spent DAYS on hold trying to reach someone at the IRS. Saw a video about this service (https://youtu.be/_kiP6q8DX5c) and it got me connected to an actual IRS agent in about 20 minutes. The agent walked me through my options for correcting prior year S Corp returns and explained the proper documentation I needed to submit. Honestly saved me from making an even bigger mess of my situation. Sometimes you just need to talk to someone official to understand your options.

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Wait, doesn't the IRS have a special business line you can call? Why would you need a service to get through? Seems sketchy to pay for something that should be free.

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Raul Neal

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I tried calling the IRS business line directly for three days straight last month and never got through. Always got the "due to high call volume" message and a hangup. How much does this service cost and are they just using some trick that we could do ourselves?

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Jenna Sloan

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They do have a business line, but it's constantly overwhelmed. I tried calling directly for over a week - either got disconnected or was on hold for 2+ hours before having to hang up for other commitments. The service basically holds your place in line for you. They have some system that navigates the phone tree and waits on hold, then calls you when an actual agent picks up. Not sure exactly how it works technically, but the end result is you get to speak with a real IRS agent without spending your whole day listening to hold music.

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Raul Neal

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I'm back and need to admit I was wrong to be skeptical. After struggling for another week trying to get through to the IRS myself, I finally used Claimyr yesterday. Got a call back in about 45 minutes with an actual IRS agent on the line! The agent walked me through my options for dealing with my S Corp election issues and missing returns. Turns out I qualified for first-time penalty abatement which the agent helped me apply for right on the call. That's going to save me over $1,200 in penalties! Also got clear instructions on exactly which forms I needed to file for the back years. Having an actual conversation instead of trying to interpret the IRS website made everything so much clearer. If you're dealing with S Corp issues like the original poster, getting actual IRS guidance is super helpful.

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Sasha Reese

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Something else to consider - if you only formed the S Corp in mid/late 2021, you might have income from early 2021 that was legitimately earned as a sole proprietor before the S Corp was formed. You need to make sure you're distinguishing between pre-S Corp income (which would go on Schedule C) and S Corp income (Form 1120-S). Also, if you didn't make a formal S Corp election with Form 2553, you might actually be a C Corp by default, which would be a whole different tax situation. Do you remember filing Form 2553?

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Kiara Greene

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That's a really good point. I started contracting around April 2021 and didn't form the S Corp until September. So I definitely had some income before the corporation existed. And yes, I'm pretty sure I filed the 2553 - the bookkeeper handled that paperwork and I signed it. I got something back from the IRS confirming the S election but I'd have to dig through my files to find it.

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Sasha Reese

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That's good you filed Form 2553 and have confirmation. Your approach should be to file two different types of returns for 2021 then: For January-August 2021, report your contracting income on Schedule C as a sole proprietor. This will be part of your personal 1040. For September-December 2021, file an 1120-S for your S Corporation. You'll need to report any reasonable salary you should have taken (even if you didn't actually run payroll) and any distributions you took from the business.

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Jumping in to add another perspective - I went through something similar last year and learned that operating as an S Corp without proper salary payments can be a red flag. The IRS looks specifically for S Corps that don't pay reasonable salaries to owners to avoid payroll taxes. If you decide to keep the S Corp status and file 1120-S forms for those years, make sure you work with a tax pro to determine a reasonable salary amount. You might need to file amended payroll tax returns too.

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Noland Curtis

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I use TurboTax Business for my S Corp. Would that work for someone in OP's situation or is this too complex for DIY software?

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