I've been dealing with IRS payment issues myself, and one thing that really helped was requesting a complete account transcript (Form 4506-T) before even trying to call. This shows exactly how every payment was processed and applied, which gives you concrete evidence to discuss when you do get through. In my case, I discovered that three of my payments had been applied to estimated tax penalties from a previous year instead of my current payment plan. Without that transcript, I never would have known to ask about it specifically. Also, try calling the Practitioner Priority Service line if you have a tax professional who can call on your behalf - the wait times are often shorter. If you don't have a tax pro, some enrolled agents will make calls for a reasonable fee, which might be worth it given how much time you're spending on hold. One more tip: if you do get disconnected after a long hold, immediately call back. Sometimes you'll get placed higher in the queue if the system recognizes you were recently disconnected. It's not guaranteed, but I've had it work a couple times. The whole situation is incredibly frustrating, but don't lose hope! Every person I know who's dealt with this eventually got it resolved once they found the right person to dig into their account properly.

I'm so sorry you're going through this - it's absolutely maddening when you're doing everything right by making your payments faithfully, but the system just isn't reflecting it properly. The combination of unresponsive phone lines and mysterious balance issues creates such unnecessary stress! After reading through everyone's experiences here, it seems like there are several common culprits for payment plan balance issues: payments being applied to penalties/interest first instead of principal, payments going to the wrong tax year, SSN or name discrepancies causing payments to sit in "suspense accounts," or simple processing delays that can take 6-8 weeks. For getting through by phone, the Tuesday/Wednesday 7 AM Eastern strategy really seems to be the most successful approach based on what others have shared. I'd also recommend having a specific checklist ready: ask them to verify your SSN matches exactly, check if any payments are in suspense, get a breakdown of how payments were applied (principal vs penalties vs interest), and confirm which tax year each payment was applied to. The Form 4506-T transcript request that someone mentioned is brilliant - having that payment history documentation before you call will give you concrete evidence to work with instead of just describing the problem. Don't give up! This is clearly a widespread issue, but everyone who's persisted has eventually gotten it resolved. Your $1,350 in payments are in the system somewhere - it's just a matter of getting the right person to track them down and apply them correctly to your account.

This thread has been incredibly educational! I'm dealing with a similar situation with old freelance tax debt from around 2016-2017, and I had no idea there were different types of "currently not collectible" status until reading everyone's experiences here. What really stands out to me is how the "not due to hardship" CNC status might actually be more favorable than the hardship-based one. The fact that the IRS isn't actively monitoring your finances or expecting you to eventually move to a payment plan seems like a significant advantage. @Ethan Davis, your situation is particularly compelling - if those 2014/2015 tax years were really assessed in 2015, you could be looking at collection statute expiration dates coming up very soon! Combined with your current CNC protection, that timing could be incredible. @Eve Freeman's firsthand account of actually having a tax year expire under the 10-year statute was so reassuring to hear. The fact that it just quietly disappeared from the transcript without any formal notification makes the whole process feel much more real and achievable. I'm definitely going to get my own transcripts analyzed to understand my assessment dates and timeline better. This community has provided more valuable insights than I've found anywhere else - thank you all for sharing your real experiences with navigating these complex IRS situations!

Thank you everyone for such detailed responses! This has been incredibly helpful in understanding my situation. After reading through all your experiences, I'm definitely going to dig into my transcripts to get the exact assessment dates for my 2014/2015 tax years. @Eve Freeman, your firsthand account of actually having a tax year expire is exactly what I needed to hear - knowing it just quietly disappears from the transcript without fanfare makes this feel much more real and achievable. Based on what several of you have mentioned about the timing, I think I need to be very strategic here. If my 2014 taxes were indeed assessed in early 2015, I could potentially be looking at expiration dates in just a few months. The fact that I'm already protected by the "not collectible not due to hardship" status while this timeline plays out seems like it could be ideal. @QuantumQuest and others who mentioned avoiding unnecessary contact with the IRS - this really makes sense to me now. I was originally thinking I should proactively reach out to "get ahead of" my situation, but it sounds like that could potentially backfire if I'm already in a favorable position. I'm going to focus on getting complete clarity on my assessment dates and collection statute timeline before making any moves. The "strategic patience" approach that several of you have described feels like the right path given my circumstances. I'll definitely update this thread once I have a clearer picture of my exact timeline. Thank you all for sharing your real experiences - this community has been invaluable!

I appreciate all the detailed responses here! Based on what I'm reading, it sounds like filing 2023 first is definitely the safer approach. The technical point about prior year AGI verification for e-filing is particularly compelling - I'd rather not deal with rejection codes and delays. One follow-up question: since my 2023 return is now quite late, should I expect any specific complications during processing? I'm wondering if late-filed returns get flagged for additional review or if they generally process at the same speed as on-time filings. Also, given that I mentioned having investment gains, are there any special considerations for capital gains reporting on late-filed returns that I should be aware of? Thanks again for all the guidance - this community has been incredibly helpful!

As a newcomer here, I want to echo what others have said about filing 2023 first, but also share a practical tip that helped me when I was in a similar situation. When you do file your 2023 return, consider using certified mail if you're paper filing, or keep detailed records if e-filing. Since it's late, having proof of submission date can be crucial if any questions arise later. Also, if you owe money on the 2023 return, you might want to pay any taxes due immediately when filing to minimize additional interest charges. The IRS continues to charge interest on unpaid balances even after you file the return. I learned this the hard way when I delayed both filing AND payment - the interest really adds up over time!

Don't overlook the potential mileage deduction! For 2023 its 65.5 cents per mile for business travel in your truck. If your driving a lot for these contracts that really adds up. Just make sure you keep a detailed mileage log (i use the stride app). You can either do actual expenses or the standard mileage rate but not both.

Just to add another perspective - I went through this exact same decision last year when I started my handyman business. I ended up going with a single-member LLC for the liability protection, especially since I'm working with power tools and heavy equipment on client properties. The peace of mind is worth the small additional paperwork. One thing I wish I'd known earlier: if you're buying that pickup truck, look into whether you qualify for the full Section 179 deduction (up to $1.16 million for 2023) vs. regular depreciation. For vehicles over 6,000 lbs GVWR used primarily for business, you might be able to deduct the full purchase price in the first year instead of depreciating it over time. This could be huge for your tax situation, especially if you're expecting a loss this year anyway. Also, keep every single receipt and document everything. The IRS gets picky about vehicle and equipment deductions, so having bulletproof records is essential.

I had this exact same issue two years ago with a 1099-NEC that had my last name spelled "Johnson" instead of "Johnston" - just missing one letter. I was stressed about it too, but it turned out to be a non-issue. I ended up filing with my correct name spelling on the return and reported the income exactly as shown on the form. No problems whatsoever - my return processed normally and I got my refund without any delays or questions from the IRS. The key thing everyone's mentioned is absolutely right - the SSN is what matters for their matching system. I did reach out to the company for a corrected form initially, but they were slow to respond and I didn't want to delay my filing. In the end, it wasn't necessary anyway. If you're planning to file in the next couple weeks like you mentioned, I'd say go ahead and file with the misspelled form. Just make sure to use your correct legal name on your tax return and report all the income shown. You can still request a corrected form for your records if you want, but don't let it hold up your filing.

I've dealt with this exact situation multiple times as a tax preparer, and I can confirm what others have said - a misspelled last name on your 1099-MISC won't cause filing issues as long as your SSN is correct. The IRS matching system is primarily based on your Social Security Number, not the exact spelling of your name. When you file your return, use your correct legal name as it appears on your Social Security card, but report the income exactly as shown on the 1099-MISC (even with the misspelled name). You don't need to delay your filing to wait for a corrected form. If you want to request one for your records, that's fine, but it's not necessary for tax filing purposes. The most important thing is that you report all the income shown on the form and that your SSN matches. I've never seen a return rejected or flagged solely because of a name spelling discrepancy when the SSN was correct. File with confidence using your correct information!