Don't forget the important part about maintaining your liability protection! An LLC that mixes personal and business finances can lose its liability shield through what's called "piercing the corporate veil." Start using that business account exclusively for all business transactions going forward.

I went through this exact same situation when I started my photography business! Don't stress too much about the mixed accounts from the past few months - it's super common for new business owners. Here's what I learned from my CPA: You absolutely can claim those business expenses you paid from your personal account. Just make sure you have receipts and can clearly show they were for business purposes. I kept a simple spreadsheet with the date, amount, what it was for, and marked it as "paid from personal account." For the business income that went into your personal account, you don't need to physically transfer it to your business account now. Just document it properly for tax purposes. $3500 for bookkeeping seems really steep for a new business unless you're doing serious volume. I'd suggest trying to handle it yourself first with something like QuickBooks or Wave, then consider hiring help once you're making enough to justify that cost. The key thing moving forward is using that business account for everything business-related. It'll make your life so much easier come tax time next year!

Have you considered using a Certified Acceptance Agent? They can help with ITIN applications and often have direct lines to the IRS. Might save you some headache.

I went through something similar with my nephew's ITIN application last year. The key thing that helped me was actually going to a local IRS Taxpayer Assistance Center in person. I know it sounds old-fashioned, but sometimes face-to-face interaction gets better results than phone calls or mail. You can find your nearest location on the IRS website and make an appointment. Bring all your documents (originals AND copies) and that letter you received. The staff there were able to tell me exactly what was missing and helped me resubmit everything correctly. It took about 6 weeks after that to get approved. Good luck!

I'm in almost the exact same boat! Filed through TurboTax two days ago and just found a 1099-DIV I missed. Mine's even smaller - only about $15 in additional tax owed. Reading through everyone's responses here is super reassuring. Based on what the tax preparer mentioned about the IRS matching program not running until later in the year, I think I'm going to follow the consensus advice: let my original refund process, then file the amendment right after I receive it. The peace of mind from getting official IRS guidance (like what people got through that Claimyr service) would probably help, but honestly the advice here seems pretty consistent. Sometimes being too eager to fix a small mistake can actually make things worse, which is counterintuitive but makes sense given how the IRS processes returns. Thanks everyone for sharing your experiences - it's really helpful to know I'm not the only one who's done this!

I was in a very similar situation last year - filed electronically and then found a missed 1099-DIV about a week later. The dividend was small (around $45 in additional tax) and I was also expecting a substantial refund. After researching and calling the IRS (took forever to get through), I learned that filing an amendment before your original return processes can actually delay everything significantly. The agent I spoke with confirmed what others have mentioned here - during filing season, they're focused on processing returns as submitted, not cross-checking against information returns. I ended up letting my original refund process normally (got it in about 3 weeks) and then immediately filed Form 1040-X with the corrected information. The amendment took about 4 months to process, and I simply sent them a check for the additional tax plus a small amount of interest. The key thing the IRS agent told me was that being proactive about correcting it (rather than waiting for them to catch it) actually works in your favor. It shows good faith and typically results in minimal penalties, if any. For your $29 situation, I'd definitely recommend the "wait for refund, then amend" approach based on my experience.

There's one thing nobody mentioned yet - the tax basis of your business for eventual sale. Make sure you're tracking your adjusted basis correctly! Even though you didn't claim the amortization expense on Schedule C, if you reported it on Form 4562, your basis in the goodwill is still being reduced each year. When you sell, your gain calculation will use this reduced basis. If you don't fix this issue with amended returns/Form 3115, you could end up paying tax on a larger gain than you should - effectively getting taxed twice!

This is a really thorough discussion! I'm dealing with something similar but with equipment depreciation on my Schedule C business. Reading through all these responses, it sounds like the key is having that Form 4562 documentation to show the IRS that you were tracking the depreciation properly, even if it didn't make it to the expense line. One question I haven't seen addressed - when you file the amended returns for the open years, does the IRS typically process those refunds quickly? I'm worried about cash flow since we're talking about potentially significant refund amounts. Also, has anyone had experience with the IRS questioning why these deductions were missed in the first place during the refund process? The taxr.ai tool mentioned earlier sounds interesting for identifying these issues systematically. I'm wondering if anyone has used it specifically for equipment vs. intangible asset depreciation issues?

Wait, I'm confused about this W-4 form. I have 2 jobs too and I think I did mine wrong. For step 2, did you check box c or did you fill out the multiple jobs worksheet? And how much extra withholding did you put for line 4c?

This is a really comprehensive discussion! I'm in a similar boat but with a twist - my employer is making the switch from contractor to employee retroactive to my start date, which means they're going to issue me a corrected W-2 for the whole period instead of a 1099-NEC. Has anyone dealt with this retroactive situation before? My HR department says they'll adjust my future paychecks to account for the taxes they should have been withholding all along, but I'm worried about how this affects my cash flow. They're basically going to take out several months worth of back-taxes from my upcoming checks. Also, since they're handling it retroactively, do I still need to worry about estimated quarterly payments or does this take care of everything? I don't want to overpay if the employer withholding will cover it all.