Thanks for this perspective! I just checked our W-4s online through our employers' portals and yep - neither of us had checked that "two jobs" box. Do you think it's worth trying to get an extension to file since we owe so much? And will we get hit with underpayment penalties?

You can absolutely file for an extension using Form 4868, which gives you until October 15 to file your return. However, it's important to understand that this is only an extension to file the paperwork, not an extension to pay what you owe. You'll still need to estimate and pay your tax by the regular deadline to avoid penalties and interest. Regarding underpayment penalties, you might avoid them if you meet one of the safe harbor provisions: if your withholding and estimated payments cover either 90% of your current year tax or 100% of your prior year tax (110% if your AGI was over $150,000). If you were getting refunds in previous years, you might qualify under the prior year tax safe harbor, but you should check your specific situation.

The online portal is perfectly fine to use for W-4 adjustments. For most people with two relatively similar-paying jobs (like married couples where both work), simply checking the box in Step 2(c) is the easiest approach. This basically tells your employer to withhold at the higher single rate rather than the married rate. If your jobs have very different salaries, or you have more than two jobs, the multiple jobs worksheet or the IRS withholding calculator will give you more accurate results. You'd enter an additional amount to withhold in Step 4(c) based on those calculations.

This is so helpful - I never thought about using my diagnosis as part of explaining the late filing. Do you have any tips on what specific wording worked for you? I'm worried about explaining it wrong.

Focus on how your specific symptoms impacted your ability to complete tasks like tax filing. In my letter, I explained how executive dysfunction made organizing financial documents overwhelming, and sensory processing issues made working with numbers for extended periods impossible during certain times. Be straightforward and factual. Something like: "Due to diagnosed ADHD and depression, I experienced severe executive dysfunction during [time period]. Despite my attempts, I was unable to organize financial information and complete tax filing processes. I am now receiving appropriate treatment and have implemented systems to ensure timely filing going forward." Attach a brief letter from your healthcare provider confirming your diagnosis and treatment timeline if possible. Keep it under one page total, and include your contact information and tax ID number on the letter.

That's not right. Form 843 is only for requesting abatement of certain penalties AFTER you've filed your return and received a penalty notice. It doesn't apply to unfiled returns. The OP needs to file their returns first, then address penalties if they receive a notice.

Thanks for mentioning the state unemployment taxes - I completely forgot about those! Do you know if the QuickBooks payroll service automatically handles those filings or is that something I need to set up separately? And any recommendations on finding a bookkeeper just for year-end stuff? Would I search for someone who specializes in "year-end closing" specifically?

QuickBooks Payroll handles federal and most state payroll taxes, but whether it includes unemployment taxes depends on which tier of service you have. With the higher tiers, they'll calculate and file these automatically, but with basic service you might need to handle filing yourself even if they calculate the amounts. For finding a year-end bookkeeper, I'd recommend searching for someone who specializes in "small business bookkeeping" and specifically mention you need "year-end closing and tax prep assistance." Many bookkeepers offer one-time cleanup services or quarterly/annual packages rather than requiring ongoing monthly work. Check the American Institute of Professional Bookkeepers directory or platforms like Upwork where you can filter for people with QuickBooks and tax prep experience.

Does QuickBooks handle the e-filing of 1099-NEC forms? I've been using QB for years but always had my accountant handle the actual filing part.

Thanks everyone for the advice! Quick follow-up question - does getting an EIN mean we have to do anything special with state taxes or is that just for federal?

Getting an EIN is primarily for federal tax purposes, but you'll likely also need to register your business with your state. Most states have a separate business registration process and may issue you a state tax ID number that's different from your federal EIN. You'll need to check your specific state's requirements, but typically you'll need to register with your state's department of revenue or taxation, especially if you'll be collecting sales tax. Many states have online portals now that make this process fairly straightforward.

Be careful with S-Corps though - they require more paperwork, formal payroll processing, and you really need to justify that "reasonable salary." My accountant said for businesses making under $75k in profit it's usually not worth the extra hassle.

Does writing in red actually make a difference? I've never heard of that before. Also, do you have to redo all the calculations from scratch or just the changed portions for the second amendment?

The red ink absolutely helps - it flags the return for special handling in the processing centers. IRS employees are trained to look for these markings on paper returns. It's an old-school trick but still works. For calculations, your second amendment needs to show the correct final figures for your entire tax situation, not just the changes from the previous amendment. Think of each amendment as a complete replacement of your return, showing what it should have been if all information had been available originally. The "changes" column on Form 1040-X should show the difference between your last filed amendment and this new one, not between the original return and this one.

I filed an amended return in December and just got it processed last week, so that's about 3.5 months. My brother filed his in February and already got his processed though, so it seems inconsistent. Might depend on complexity or just luck of the draw.