I've been following this thread closely since I'm in a similar situation with about $145k in 1099 income this year. The consensus seems clear that retroactive S Corp election isn't possible, but I wanted to add a few practical considerations I've discovered while researching this. First, if you do decide to form the LLC in December, make sure you understand your state's publication requirements. Some states like New York require you to publish a notice in local newspapers, which can cost $1,000+ and take several weeks. This could delay your ability to get everything set up cleanly. Second, I've been talking to several CPAs about the "reasonable salary" issue that keeps coming up. The general rule of thumb I'm hearing is 60-70% of your net profit should be salary, with the rest as distributions. But this varies significantly based on your industry and role. For consulting/contracting work like ours, they're suggesting looking at comparable W-2 salaries for similar roles in your area. Third, don't forget about state-level considerations. Some states don't recognize S Corp elections or have additional franchise taxes that can eat into your federal savings. Has anyone here dealt with multi-state issues? I have clients in 3 different states and I'm worried about creating nexus issues with an LLC that I don't have as a sole proprietor.

I'm dealing with a very similar situation and want to thank everyone for the detailed responses here. I'm at about $128k in 1099 income this year and was also hoping I could somehow make an S Corp election work retroactively. One additional consideration I haven't seen mentioned - if you're planning to make this transition, start thinking about your 2026 estimated tax payments now. When you switch from sole proprietor to S Corp, your quarterly payment calculations become more complex since you'll have both payroll taxes and potential distributions to account for. I spoke with my accountant yesterday and she mentioned that many people underestimate their Q1 2026 payments because they forget that the "reasonable salary" portion will have payroll taxes withheld throughout the year, but any distributions taken early in the year won't have taxes withheld. This can create a cash crunch at tax time if you're not careful. Also, for those asking about the actual savings - I ran the numbers with my CPA and at my income level, we're looking at roughly $6,800 in annual self-employment tax savings after accounting for payroll processing costs and additional filing fees. That's definitely worth the extra administrative burden for me. The liability protection alone makes forming the LLC worthwhile even without the immediate tax benefits. Better to get everything set up properly now rather than rushing through it in January when everyone else is trying to do the same thing.

Most tax software handles this automatically now. I use TaxAct and when I entered more than 14 interest payers, it created the attachment for me and formatted everything correctly. Same with H&R Block online - it just keeps letting you add payers and handles the "overflow" in the background. If you're filing on paper or using software that doesn't handle this, definitely go with the attachment method others mentioned. But might be worth checking if your tax software already solves this for you!

Great question, Malik! I ran into this exact same issue two years ago when I had 19 different interest-paying accounts. Here's what I learned works best: The cleanest approach is to use a combination of the methods mentioned here. First, combine any accounts with less than $10 in interest into a single "Various - Small Accounts" line as Chloe suggested. This alone might free up enough lines. For any remaining overflow, create a simple attachment following Freya's advice. I used a basic Word document with three columns: "Payer Name," "Amount," and "Line Number" (continuing from where Schedule B left off). At the top, I included my name, SSN, and labeled it "Schedule B Continuation Sheet." On Schedule B itself, I used one of the last lines to write "See attached continuation sheet" and included the total from the attachment. The IRS processes thousands of these every year - it's completely normal. As long as you report all your interest income accurately, you won't trigger any red flags. In fact, being thorough like this actually reduces audit risk since it shows you're being careful and complete with your reporting. Keep copies of all your 1099-INT forms and the attachment for your records. Good luck with your return!

One thing to keep in mind when dealing with multiple 1099 forms - make sure you're checking for any backup withholding that might have been taken out. Some of your 1099s might show federal tax withheld (usually in Box 4 for 1099-INT or Box 6 for 1099-DIV) if you didn't provide a correct TIN or if you were subject to backup withholding for other reasons. This withheld tax gets credited to you just like regular tax withholding from your paycheck, so you want to make sure you're capturing all of it when you file. TurboTax should pick this up automatically when you enter your 1099 information, but it's worth double-checking that the total federal tax withheld on your return includes any backup withholding from your investment accounts. Also, don't forget that some 1099-DIVs might have state tax withheld too, which you'll need to report on your state return if your state has income tax.

One additional tip for organizing multiple 1099s - create a simple spreadsheet or table before you start entering data into TurboTax. List each financial institution, the type of form (1099-INT vs 1099-DIV), and the key amounts from each box. This gives you a clear overview and helps catch any discrepancies. I learned this the hard way when I had to go back and figure out why my totals didn't match what TurboTax was calculating. Turns out I had accidentally double-entered one of my smaller savings account 1099-INTs. Having everything laid out in a spreadsheet first would have made it much easier to spot the duplicate entry. Also, if you have any 1099s that arrive late (after you've already filed), don't panic. You can file an amended return (1040X) to include the missing income. It's better to be accurate than to rush and miss something.

Great thread everyone! As a newcomer to this community, I really appreciate all the detailed advice about handling 1099-R forms. I'm in a similar situation with my first retirement distribution and was getting overwhelmed by all the boxes and codes. Reading through all these responses, it's clear that the EIN is the critical piece for IRS matching, but entering the payer name exactly as shown is the safest approach. I love that people shared their actual experiences - especially hearing from the tax prep professional about what constitutes "minor" vs "problematic" variations in payer names. The tips about double-checking federal withholding in Box 4 and state withholding in Box 12 are gold - I almost missed those on my form! And I had no idea about the distribution codes in Box 7 being so important for determining tax treatment. This kind of detailed, experienced-based advice is exactly why I joined this community. Looking forward to contributing back once I get more familiar with all these tax forms and processes. Thanks again everyone for making this less intimidating for us newcomers!

Welcome to the community! This is exactly the kind of detailed discussion that makes this forum so valuable. I'm also dealing with my first 1099-R this year and was feeling pretty overwhelmed by all the different boxes and requirements. The consensus here about using the EIN as the primary matching element while still entering the full payer name exactly as shown is really helpful. I've been second-guessing myself on every field, but it sounds like being precise with "FIDELITY INVESTMENTS INSTITUTIONAL OPERATIONS CO." is the way to go. I also want to thank everyone who mentioned checking Box 4 for federal withholding and Box 12 for state withholding. I just went back to my form and realized I had federal taxes withheld that I need to claim as withholding on my return - would have completely missed that! One follow-up question for the group: if I discover I made an error in how I entered the payer name after I've already e-filed, is that something that typically requires an amended return? Or do minor discrepancies in payer names (assuming the EIN and amounts are correct) usually not cause issues that need correction? Thanks again for all the great advice - this community is incredibly helpful for navigating these tax complexities!

Anyone else think its crazy how much we pay for TurboTax when FreeTaxUSA does basically the same thing??? I switched 3 years ago and have saved like $300 total! The only thing I miss is the audit protection but never had an audit anyway lol

I made the exact same switch last year and can confirm everything others have mentioned. The first year is a bit of a pain since nothing carries over, but it's totally worth it for the cost savings. One tip that helped me: I kept my previous year's TurboTax return open on a second screen while filling out FreeTaxUSA so I could manually reference things like prior year AGI, estimated tax payments, and other carry-forward items. It made the transition much smoother. Also, don't be surprised if FreeTaxUSA's interface feels a bit bare-bones compared to TurboTax's fancy graphics and animations. I actually prefer it now - less hand-holding but more straightforward. Plus their state returns are only $15 compared to TurboTax's $50+ state fees. You'll love the savings!